Retreats bring us new energy and ideas. We bond, brainstorm, and collaborate in person. For a remote team like Canny, these retreats offer the in-person interaction we miss. This retreat had a big goal—to launch Canny Autopilot. Here’s what went down in Perugia.

Preparation

Retreats always need extensive preparation. As the team grows, we need to think through everything even more. In particular:

• Dates: what works for everyone (or at least the largest number of people)?
• Destination: which place doesn’t require visas (or issues visas easily)?
  • Where can most of the team easily get to?
  • We prefer places that offer interesting sightseeing/activities
• Accommodations: are there enough beds, bathrooms, and common areas for work?
  • Ideally, we also look for accommodations with cool features like a pool, sauna, views, large kitchen, ping pong table, and more
  • Is there good wifi?
• Food (restaurants, supermarkets, etc)
• Work meetings: who wants to talk about what? What are some high-level decisions we should all discuss? What are we trying to accomplish this time?
• Activities: what are we going to do for fun?

With 15 attendees, finding the perfect place is challenging. Early planning is key.

Assemble the troops

Eight retreat planners volunteered to help. We started with destination, accommodation, and food research.

Start planning asap

We sent out a survey with proposed dates almost immediately after the previous retreat. The sooner we lock them in, the faster we can start planning the rest.

Cross off the big things – destination & accommodations

We’ve tried different retreat formats at Canny—large cities, smaller remote towns, and something in between.

Here’s the tradeoff: in prominent cities like Tokyo, we are forced to split the group between multiple Airbnbs. It’s also harder to come together in one place and have meetings.

Smaller towns can offer larger accommodations (with fun perks like a pool, gym, theatre, and more) but don’t have that much around them.

Our post-retreat surveys revealed that most of the team prefers a cooler space over a larger city. This goes back to our goal—come together to collaborate and share ideas.

We took that feedback and prioritized smaller towns with fun Airbnbs. We also had to consider visa requirements and flight durations. This is when we have a spreadsheet going with viable options and columns relating to the cost of flights and accommodations.

We chose a town in Italy called Deruta. It’s in the province of Umbria, next to Perugia. Our primary reasons were:

• Large accommodations with just enough bedrooms, bathrooms, and common areas
• Excellent amenities like a pool, sauna, hot tub, ping pong and foosball table, gym, and even donkeys!

Collect ideas

We always set up a Canny board to crowd source ideas for the retreat.

After we have a prioritized list of ideas (based on votes, cost, proximity to our accommodations, and more), we pick the best dates for them. Typically, it’s easier to book many things on weekdays. That’s why we usually swap one or two weekdays with weekend days for work and play. This way, we avoid crowds and sometimes get a better price.

Our winning ideas this time included:

• Truffle hunting (with a dog!) and pasta-making experience
• Exploring Perugia (capital of Umbria)
• Authentic Italian cooking class at our villa

Plan work

This retreat the biggest thing on our mind was Autopilot—our AI-powered feedback management tools that we just released. We used this time to:

• Determine the final steps to get it ready for launch
• Finish writing and testing code
• Align with the rest of the team on functionality, marketing, messaging, and more 

We’ve been working on Autopilot for some time. Getting everyone together in person to tackle the final roadblocks was very impactful. Communication flows faster and easier when you’re all in one room.

We also had meetings about go-to-market priorities, customer experience, and Canny’s overall direction. Everyone could voice their concerns, ask questions, and align on our future.

Make it happen

After months of waiting, we all met in Rome. Some of us explored the city for a few hours, while others drove straight to the Airbnb.

We always do a kickoff presentation to get everyone excited and set goals for the week ahead.

We made time for fun too. The Airbnb amenities were amazing—perfect for strategic chats overlooking the Italian countryside.

During one of our days off, we went on a truffle hunting experience. A trained dog named Dado led the pack. He sniffed out the truffles, dug them up in seconds, and immediately asked for treats.

After we collected enough truffles, we explored a local winery and then learned how to make pasta and cookies from scratch. All this hard work called for some rest, so we had a wine tasting along with all the food we made. It was also Ramiro’s birthday so this was an awesome way to celebrate all together 🙂

Other highlights included exploring Perugia and Assisi and cooking an Italian dinner at our villa. It’s safe to say that we all brought home some new cooking skills.

Another highlight for me was our PechaKucha night. PechaKucha is a Japanese presentation format. The presenter is only allowed 20 slides, and they have 20 seconds per slide. It’s a quick and fun way to present anything you want.

When new team members join Canny, we ask them to do a PechaKucha about their lives. Since we’re all remote, we do them virtually.

This time, we did them in person. Anyone could do one and pick any topic they liked. As a result, we learned about:

• Bikepacking from Niall
• Fast & Furious from Ramiro
• Being a dad from Eric
• Having pet pigeons from Miko

Learning about each other outside of work is always special. We find more things in common, get new ideas, and just become closer. This helps us work together better and understand each other more.

Canny in Italy: what we learned

As we mentioned, we send out a post-retreat survey when we come back. It helps us make the next one even better.

Here’s what we learned on this retreat.

• Plan meetings more in advance and in more detail. Meetings can easily go off-script and overtake an entire day.
• Try not to schedule a major public release during the retreat. This put pressure on certain team members.
• Think about food more. Assign responsibilities in advance.
• Ensure we’ve got sufficient Internet connection.

Overall, this was another great retreat for the books. We’re now busy with planning the 10th Canny retreat!

We hope these tips will help you plan your retreat, too. Share your retreat learnings with us too—we’d love to hear about your experience.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

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The post La dolce vita con Canny: team retreat in Italy first appeared on Canny Blog.

The post La dolce vita con Canny: team retreat in Italy appeared first on Canny Blog.

However, managing mountains of feedback is tough, especially when it’s coming from many different sources. That’s why we’re excited to launch Canny Autopilot!

Autopilot is our suite of AI-powered features that automate feedback management and give you back your time.

“AI is exploding. It’s this new unlock in the world. Everybody is thinking—how can we use it to provide value to our customers? For us, there’s this obvious opportunity. Our customers are already tracking feedback. If we can do this for them seamlessly and automatically (and better than they can do it themselves), that’s a huge value-add right there.”

Andrew Rasmussen, co-founder

Autopilot uses AI to handle your manual tasks. It collects and sorts feedback, finds duplicates, replies to users, summarizes long threads, and more. This lets you focus on improving your product based on what users really need.

Our beta users are already saving time and getting better insights.

“I’m really loving the new [Autopilot] beta. It’s been awesome. It makes me engage with your product on a daily rather than every week or two. So, props to your team to developing this feature because it’s made our usage of your product to go up by a crazy amount!”

Keenan Jones, VP of Product at Credit Repair Cloud

Even if it only takes you a minute to capture feedback from a user, that still adds up to hours saved over time.

Let’s explore how Autopilot saves you time and helps you more effectively manage feedback.

What is Autopilot?

Feedback Discovery: automated feedback collection

Connect Autopilot with your favorite tools like Intercom, Help Scout, Zendesk, and Gong. Watch as it sifts through customer chats, detecting valuable feedback and funneling it right into Canny. This automation cuts down on manual sorting and ensures no feedback gets missed.

We’ve thoroughly tested and optimized our AI, and it very accurately extracts customer feedback. Autopilot is able to capture more feedback than humans.

“We don’t just have a single-stage process. We’re not going straight to the API asking, “What is the feedback here?” or “Is there a bug report in this?” Instead, we have a multi-stage process where we ask one small question at a time. This means we have higher fidelity and accuracy than competitors.

We also don’t cheap out on the models we use. No matter which Canny plan you’re on, you’re still getting the same level of accuracy with extraction and deduplication.”

Niall Dickin, engineer

We spent a lot of time building, iterating, and perfecting Autopilot’s feedback discovery. It started as a proof of concept that one of our engineers built. Then, we built an MVP and released it to beta users. After six months of beta, we’re incredibly excited to take it live.

“The rate at which the field is advancing is a little challenging. Lots of things are happening at once. Canny is a small, bootstrapped team, and we have to keep up with other projects as well.

I’ve been the dedicated engineer on this project, so my daily tasks have included keeping up with AI news, benchmarking new models, and using what’s best for our customers.”

Niall

Organize feedback in one place

Autopilot puts all new and detected feature requests in one spot. You can connect various feedback sources and automatically extract feedback from them. Autopilot will also identify duplicates and merge them to keep your feedback tidy.

You can go with full automation and let Autopilot create posts and votes for you. You’ll be able to see a log of all actions and easily undo them if need be.

Autopilot doesn’t just collect feedback. It also connects it back to the users. Even if feedback is collected automatically, we ensure users are connected to their requests. This way, you can still segment and better understand the urgency of requests. They also get updated as you work on their suggestions. This enhances user satisfaction and trust in your product.

Smart duplicate management

Autopilot is great at spotting when the same feature request pops up more than once. It merges these duplicates and upvotes them for your customers. This keeps your feedback boards clear and focused.

“Autopilot will automate and bring home feedback that would otherwise get missed. Support moves quickly. Canny Autopilot can follow behind and pick up those crumbs to help you build a better system. You don’t need to train your teams or customers to do anything new.”

Jacques Reulet, customer support

Engage better and faster with Smart Replies

Autopilot responds to every feedback post with intelligent questions that sound like you. It helps you uncover additional context. This means you can quickly ask for further details without typing everything yourself.

“You can really understand the sentiment of what your customers are asking for. This way, you can thoughtfully take care of their needs.”

Julia Valade, customer success

Save time with Comment Summaries

Autopilot can also summarize the main points from really popular ideas with many comments. This helps you see what matters most without reading through every single comment.

Seamless integrations

It’s simple to connect Autopilot with your favorite customer support tools. Whether you use Intercom, Zendesk, Help Scout, or Gong, setting it up is straightforward. We’re always adding more integrations, too.

If you have a feedback source we don’t support yet, send text in via our API endpoint and Canny will detect feedback there as well.

Why you’ll love Autopilot:

• Never miss feedback again. Be confident that you’re catching nearly all customer feedback.
• Save time. Let Autopilot handle the routine tasks so you can focus on making important decisions.
• Understand your customers better. Get a clear view of what your users really need and want. This will help you choose which features to work on next.

Not just about AI

We want to be very clear—Autopilot was not made to check the AI box. We want to transform how you manage feedback and AI helps us do that. You can count on Autopilot’s reliability and accuracy to many Canny your source of truth for feedback. With Autopilot, you can reach your goals faster.

How Autopilot fits into Canny’s vision

Canny Autopilot aligns perfectly with our vision—building better products through feedback. That’s hard to do at scale and Autopilot solves that.

Autopilot makes capturing feedback easier and more reliable than ever. With its high accuracy, you won’t miss out on valuable insights. This not only saves you time but also ensures that every voice is heard and considered.

“Canny’s Autopilot ensures feature requests never fall through the cracks. We’ve seen an 80% increase in requests logged since introducing Autopilot.”

Owen Doherty, COO, Orca Scan

A more complete and organized feedback collection process helps you better understand your users. It also lets you prioritize the features your users truly care about. This alignment with user needs drives product development forward.

Managing feedback across a growing customer base becomes challenging. Autopilot scales smoothly with your growth. It handles increased volumes of feedback without losing accuracy. This makes it an ideal solution for larger clients who need robust feedback systems to match their scale.

“We are a small, agile, and bootstrapped team. We’re not at all worried about impressing VCs with fancy terminology. Our number one investor is our customer. We aren’t going to ship functionality that doesn’t work.”

Dan Murray, engineer

Bottom line: Autopilot reduces manual work, saves time, and improves performance

Canny Autopilot takes the manual work out of feedback. This lets you focus on building better products. It makes managing feedback realistic for teams at any scale. 

Ready to put your feedback management on Autopilot?

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

All Posts · Twitter

The post Put feedback management on Autopilot—introducing our new AI features first appeared on Canny Blog.

The post Put feedback management on Autopilot—introducing our new AI features appeared first on Canny Blog.

If you haven’t seen earlier reviews, check our year one, two, three, and four.

Let’s go over some highlights from this year:

• Over $3.4m in annual recurring revenue
  I’m proud of this figure in itself but this past year has been very difficult for revenue in particular. I’ll talk about that more below.
• 17-person team
  So grateful to every person on this small but mighty team.
• 2 retreats
  We went all out to Tokyo last May and then hosted Canny Cottage in Ontario in November.
• Raised $0
  Still going strong here with no plans to change that!

I publish a series of tweets every year on the anniversary of me quitting my full time job at Meta. I’ve still managed to do those so check them out: year 5, year 6, and year 7.

1/ Today marks 5(!!) years since I left my job @facebook (@meta?). In numbers:
💰 $2,200,000 ARR
🙏 1,100 customers
💬 68 investor chats turned down
💕 9-person team
👩🏻‍💻 8 remote team hangs
🚀 1 startup, @cannyHQ
✊ 0 dollars raised

— Sarah Hum (@sarahhum) November 18, 2021

1/ Today marks 6(!!) years since I left my job @meta. In numbers:
💰 $3,500,000 ARR
🙏 607 paying customers
💬 102 investor chats turned down
💕 13-person team
✈️ 6 team retreats
🚀 1 startup, @cannyHQ
✊ 0 dollars raised

The next year ahead is going to be tough 🧵👇

— Sarah Hum (@sarahhum) November 18, 2022

1/ This weekend marked 7 years since I left my job @meta. In numbers:
💰 $3.3m ARR
🙏 583 paying customers
💕 16-person team
✈️ 8 team retreats
🚀 1 startup, @cannyHQ
✊ 0 dollars raised

This was the first year where we didn't grow. Let's unpack 🧵👇

— Sarah Hum (@sarahhum) November 21, 2023

Between the tweets for year six and seven, we see a $200k ARR drop. Yes, year six was over-reported due to a pricing change but a big part of that was also the economy. One thing’s for sure: the world was/is still struggling and we felt that. All of a sudden, growth started to feel a lot more difficult.

Navigating economic lows

As pandemic panic subsided, recession worries escalated. Interest rates climbed to combat inflation with many countries hitting multi-decade highs. In the startup world, we started hearing pretty negative outlooks for growth.

How bad will the recession be?

After analyzing revenue data from 27.2k companies: it's worse than we thought.
– B2B getting hit hardest since '08
– Consumer $$ tanking

What should you do?
– 6 ways to not lose in recessions
– 4 ways companies win in them

Thread time 🧵

— Patrick Campbell (@Patticus) November 9, 2022

While all that was happening, we launched Canny’s first Free plan. We’d been planning it for months and wanted to make Canny more accessible to early-stage startups. In hindsight, not the best timing. 

We lost around half of our paying customers overnight but more than doubled our ARPU. It hurt, but our goal was to have more teams using Canny. Now, we have over 6,000 teams on Canny Free.

In the following year, cancellations citing money problems became a lot more common. It makes sense that a lot of companies (especially funded ones) did some cost-cutting. Running lean means a longer runway. To combat this, we leaned more into annual contracts and some multi-year contracts. Our Free plan helped maintain many relationships as well.

While we are bootstrapped and profitable, we also cut our spending down where we could. Thankfully, we never got to a point where we even thought about doing layoffs.

We also make sure to keep a pulse on the market in general. It’s more helpful to benchmark ourselves against similar companies. Things have slowed compared to previous years but we’re doing alright versus other companies.

During this time, we felt it was important to make sure the team was united and pushing towards a common goal. We find our team retreats are a great way to stay connected and motivated. They aren’t cheap and require a lot of planning but they’re worth it. This last year, we met up in Tokyo(!!) and at an awesome cottage near Toronto.

I love being able to relive our trips through these videos. They’re also great for showing potential new teammates what working at Canny is like. Here’s a blog post outlining our most recent retreat and how we pull them off.

Meanwhile, we also hunkered down and continued doing what we do best—building product. 

The AI wave

You know what I’m talking about. We’re seeing tools add sparkle buttons all over the place. The button that basically says, “click me and something magical will happen”. While there are definitely some misses out there, there are also some really great uses of AI. If you’re not already, you should be considering how AI can help you be more efficient with your job.

I asked the Canny team what AI tools have been helpful for their day to days:

Engineering:

Github Copilot – it’s like autocomplete for coding, but it can also complete large swathes of text. You can also ask general coding questions. I typically use the autocomplete feature to speed up my coding.

Niall

GPT-4 – for rubberducking (but the duck talks back)

Ramiro

Support:

Intercom’s Fin AI bot has taken over more than a third of support cases. The fact that it learns from our help center is great enough, but it also learns from past conversations. It’s only getting better!

Jacques

Marketing:

GPT-4 – helping generate outlines that comprehensively cover topics while incorporating relevant keywords. Also, review large volumes of data like reviews, forum threads, etc, to find good quotes.

Eric

GPT-4 – For content creation. I never use exactly what it gives me. No matter how detailed the prompt is, I still need to edit the copy output to match our voice and tone. Still, it saves me a bunch of time I’d spend on external research and ideation.

Maria

The overall sentiment seems like these AI features help us avoid doing a lot of the manual work we used to do.

At Canny, we’ve shipped some sparkle buttons too. As Canny’s product manager, I’ve been able to take advantage of our smart replies and comment summary features. Both help me get to the information I’m looking for faster. 

The way we approach building in this AI era boils down to one question: how can we provide our customers with more value?

We ask ourselves questions like:

1. What are the most time-consuming aspects of Canny?
2. What tasks do not need to be done by a human?
3. What is the real end-value we’re trying to provide and how can we get our customers there faster?

Our next big sparkly update involves automatically identifying feedback in customer conversations. We know how important it is to capture feedback from support, customer success, sales, etc. but it’s a lot of work to stay on top of. What if Canny tracked feedback for you and automatically grouped similar ideas together?

I’m really excited about it because it takes a lot of the responsibility off our go-to-market team. Meanwhile, product still gets the feedback we need. When considering a new feature, I’m able to go in and see sentiment from customers and prospects tracked by our AI. 

We’re currently running a beta for it so if you are interested in joining, reach out to our team!

Product marketing

Our product team is building high-value features for our customers everyday. That said, we don’t have a dedicated product marketer and realized that we can do more to celebrate what we ship.

This past year, during one of our retreats, we sat down and put together a product marketing plan. The goal was to share what we’re working on without it being a lot of new overhead. Now, we’re committed to sharing a product update every three weeks. Each update involves:

• Product team declaring which features are slotted in for a specific release date
• Sending out a product updates newsletter and sending out updates on our socials
• Publishing changelog entries for each new feature

So far, our plan has worked really well. Primarily, it gives our customers more insight into what’s new in Canny. They can feel that the product is constantly improving.

Beyond that, we found benefits we weren’t expecting. This process caused some good ripple effects and discussions internally. Previously, our product development cycles were very flexible. The releases give our product team a rhythm without subscribing to a full scrum process. Outside of product, our other teams feel more connected. Positive change all around!

Founder time

I’ve talked about this before, but delegation is still very much something Andrew and I are working on. Especially as our team grows, I’ve been trying to protect my time more. We try to budget our time for things in two groups:

1. Things only we can do

For me, this includes stuff like writing this blog post! Reflections like these are fully based on personal experience—something someone else (or an AI) wouldn’t know.

I would also include product management in this list. Of course, we could hire a dedicated product manager. However, at least for now, I feel it’s very helpful for me to stay as close to the product as possible. 

2. Things that we really enjoy doing

For Andrew, this includes writing code. Over time, Andrew’s responsibilities went into covering our legal and finance needs—things he’s good at but doesn’t particularly enjoy. In the past few months, he’s found more time to get back into the codebase, and I can tell he’s happier.

“Canny kicked off well thanks to Sarah’s design magic and my engineering chops. We see these as our superpowers. Doing what we’re best at keeps us happy and does wonders for Canny.”

Andrew

Something that helps me plan my time is writing tasks down. These kinds of systems are really personal, but here’s what’s been working for me:

1) Keeping a physical journal

I use a ring planner to write down key weekly work and personal tasks. Every night, I disconnect from electronics before bed and jot down anything new on my mind. Then, I keep my planner open in front of me on my desk as a constant reminder of what I need to get done. Something about writing it down makes it feel more “real”.

2) Brain dumping specific task details digitally

The nitty gritty gets documented digitally in a tool called Ellie. I can easily move tasks between different days and timebox them as needed. I also use an iOS shortcut on my phone that creates Ellie tasks for me when I’m out and about. It feels really good knowing that I don’t need to store everything in my brain.

This past year, I looked back at the tasks I was doing repeatedly and asked myself what I could delegate. This usually requires some upfront work to train a new person. Once that’s done, it makes a huge difference.

The biggest changes we made to create space involved internal team restructuring.

Team changes

Team changes are often really challenging, and we had to make some tough decisions this last year. That said, I’m confident we are stronger for it.

Starting with the challenging parts: we moved people around to make the best use of their strengths. As managers, it’s important for us to identify and recognize the strengths of our team. In some cases, there might be a mismatch between the person and the role they’re in. The best thing to do in that scenario is to make a change. This can be a painful process, but it’s definitely worth it.

Moving onto management. While we still consider ourselves a very flat organization, we needed help here. It’s been great to have a few people step up and dedicate brain space to help our teams work effectively and happily. While Andrew and I were doing a lot of this management before, we weren’t great at it. Our time was much too divided to give people the attention they deserved.

Onto exciting parts: opening new roles! When we find gaps, we look for someone to fill them. This year we brought on Clare to help us out with all things operations. She now also leads our go-to-market teams, helping them identify opportunities for impact. One of the people Clare works with is Julia, who came onboard to take on our customer success needs. This is especially important to us given our focus on retention.

Another role that we wanted to fill this year was support engineering. Previously, we had our engineering team do a support rotation. Over time, it proved to be quite disruptive to core product work.

At first, we looked for an entry-level engineer to handle technical support questions. However, one of our engineers, Sara, stepped up to fill this need and so much more. She is now our customers’ point of contact for technical issues. Sitting between our product and go-to-market teams is also beneficial. She spots opportunities for improvement in our processes and communications across teams. We now refer to her as our go-to-market engineer.

“As an engineer at Canny, I deeply appreciate the opportunity to work for a company that values direct engagement with our customers. By dedicating engineering team members to work closely with users, we gain invaluable insights into their workflows. This enables us to fully leverage the power of Canny and swiftly implement functionalities that align with our customers’ goals.”

Sara

Last but not least, we hired our first virtual assistant! Steph is from the Philippines and helps out with a bunch of our miscellaneous tasks. These range from finding our retreat accommodations, to keeping our task statuses up to date, to building an AI benchmark dataset. These might seem like small tasks, but they add up to a lot over time. 

Our team changes this last year made a huge difference in our overall impact as a team.

Personal updates & goals

We are so much more than our day jobs! All of us at Canny enjoy life outside of work.

Andrew and I were able to go on a few trips including a month in Korea, Japan, and Taiwan, and a spontaneous trip to Hawaii. It’s very different from being digital nomads, but I always enjoy an adventure.

Outside of that, we mostly enjoyed our quiet life in Toronto with our dog, Emmy. 

I personally spend most of my free time on hobbies. I started a little side hustle making artisan keycaps out of polymer clay. Through that, I’ve learned that I get a lot of joy out of creating something with my hands, shipping it to someone, and then seeing them love it. 

The other big thing for me is journaling. I’ve been writing in my journal every day since January 1st this year, and I plan to for the rest of the year. I’ve found appreciation for documenting things that I know I’ll enjoy looking back at years from now. I’m also happy I can finally make use of all of the stationery I’ve been collecting for so long.

This is technically not in the last year but we’re moving to Seattle next month! It was a complicated and sudden decision, but we’re looking forward to being back on the west coast. If you’re in the area, say hi!

The team had some awesome accomplishments this last year too:

• Jacques: Got married and moved to Mexico.
• Maria: Is working out consistently and learned at least five songs on the guitar.
• Eric: Became a dad and won first place in some Updog frisbee games with his pup, Cloud Strife.
• Kaman: Joined Canny, opened an Etsy shop, got married, and climbed Mount Fuji.
• Ramiro: Ran his first 20k, traveled a bunch, and learned to snowboard.
• Dan: Started doing local sauna popups in Madison, WI. Check out the Smokin’ Barrel Sauna.
• Julia: Joined Canny and is learning Spanish, sewing, and salsa.
• Adam: Had a baby who is coming up on 10 months old.

Year 8

We are inching closer to double digits—wild.

During hard times, I’m especially grateful for our amazing team. While we’re working remotely, we are trusted to deliver. A lot of cool product stuff is coming down the pipeline, and I’m excited for our customers to see them. Our go-to-market team is on deck to make sure everyone knows the value Canny brings to software development. 

Stay tuned especially to our next big AI-powered features. We are pushing hard to nail down the experience and quality. Join our Discord if you want the inside-scoop.

When we can get together in person, the focus is on team bonding. We work better together when we know each other better as people. Our next retreat is in Italy in May!

We feel good about our team at the moment, so we’ve slowed down hiring. I love having a small but mighty team. That said, this could change! Keep an eye on our jobs page if you’re interested in being a part of team Canny.

I’m hopeful that year eight will be a significant year in our story. Onwards!

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

All Posts · Twitter

The post Year in review: 7 years of running our profitable bootstrapped SaaS first appeared on Canny Blog.

The post Year in review: 7 years of running our profitable bootstrapped SaaS appeared first on Canny Blog.

It’s a unique blend of personal and professional worlds. Is it always a good idea, though?

Combining personal and business relationships brings its own set of challenges and rewards. It demands clear communication and a shared goal. You need to learn to navigate both personal and professional challenges together.

You’ll face work stress together, which can lead to more disagreements. Work becomes a major part of your lives and it could come at the cost of a happy personal life.

Andrew and I started Canny together over seven years ago. While I believe working together has strengthened our relationship, I wouldn’t say it’s been an easy journey. Mutual respect and complementary skills helped us get to where we are today.

I’m writing this based on the interview we did in this video so watch that if you prefer. It was fun because we both answered the same questions separately and got to see how our responses differed.

Alright, here are some tips for starting and running a business with your significant other. First, let us introduce ourselves.

Who is Sarah?

I’m Sarah, one of the co-founders at Canny. I studied graphic design in university and my first full-time job was at Facebook. That’s where I met Andrew and where the seeds for Canny were planted. I’ve always been passionate about design and how it can solve real-world problems.

Today, I focus on crafting a functional and user-friendly product design. I thrive on creating products that people love to use. I also spend lots of time trying to understand our users’ needs. On top of this, I juggle many other hats—from marketing to customer support. I enjoy being involved in so many aspects of the business.

It’s not all smooth sailing though. As a co-founder, making tough decisions is part of the job. Letting people go, cutting costs, and deprioritizing exciting projects are just some examples. It’s challenging, but it’s also what makes this journey exciting.

Who is Andrew?

Andrew is my co-founder and the one who built Canny’s foundation. Today, he makes sure our platform is not just up and running but also constantly evolving to be better. He’s heavily involved in shaping our product strategy and many behind the scenes functions that keep Canny going. When he can find the time, he still enjoys coding.

He’s also incredibly dedicated, sometimes to the point where it’s hard for him to step back and take a break.

“I really like talking about work. I can talk about it for hours. I find it really fun, even if you’re not making any material progress. It’s almost therapeutic for me. Sarah is not like that, so she’s the one who maintains our balance.”

Andrew Rasmussen, co-founder of Canny

Canny’s origin story

It all started at Facebook, where I began as a design intern. Andrew was starting his full-time engineering job, and we met through mutual friends. It wasn’t long before we realized we had much more in common than just our workplace. We began collaborating on small projects and participating in hackathons.

“One memorable experience was at an AT&T event in Las Vegas. Our team won the hackathon, and the prize was $45,000. This wasn’t just a victory for us; it was a turning point. It made us think: “Maybe we can really do this—build products together.”

Andrew

Realizing we work pretty well together, we looked for something we could turn into a real business.

Canny’s evolution

Early versions of Canny were targeted at consumers and attempted to give them a say in the roadmaps of products they were using. We soon realized that we had it backwards: we needed to go to the companies who wanted to process that feedback. We shifted our focus to B2B SaaS companies. This change really transformed Canny into what it is today—a comprehensive feedback management tool for software teams.

Every step of the way, we leveraged our strengths—my design expertise and Andrew’s engineering skills. This synergy drove product development and helped us grow quickly.

Working together

When you work with your significant other, having clear roles is essential. In our case, it was easy. We capitalize on our individual strengths.

A part of why we work well together is because we have complementary skills. It’s not very helpful for co-founders to have the exact same skillset. We balance each other well.

Andrew is an engineer, so he has a final say in everything related to engineering. He also works on our business vision, revenue, compliance, and legal.

I’m a designer, so I’m in charge of design. I also get involved with product, marketing, customer service, and other areas.

Lesson: Assess your skills and capitalize on your strengths. Have defined roles from the start. The other stuff will fall into place as you go.

Aligning our vision for Canny

We often discuss and reassess our goals to ensure we’re on the same page. Our alignment comes from understanding each other’s perspectives and finding common ground. We don’t always agree. Over the years, we’ve learned to “disagree and commit.”

“We don’t always see eye to eye, but we can make most decisions together. You don’t have to get every decision perfectly right. We certainly don’t, and that’s OK.”

Andrew

Suppose one of us has strong convictions about a particular decision. In that case, the other partner is open to trying it out. Ultimately, it’s about trusting each other’s judgment and committing to our joint decisions. If the decision turns out to be the wrong one, we adjust, no harm done.

One of my favorite things about our relationship is trust. It’s easy to take things personally but we both trust each other to make the best decision for the business

Lesson: Trust your partner to own decisions in their area of expertise. Otherwise, when you need to make a decision and don’t agree, try “disagree and commit.” 

Being a couple

When you run a business with your significant other, work can quickly take over every conversation. Andrew and I manage this by setting clear boundaries. We have a rule: discuss work for a limited time, then switch off. When we walk our dog, we can talk about work on the way out but no work talk on the way back.

We are very intentional about these boundaries so that we have space for our personal lives.

“It’s all about finding that switch between work and play modes. Regardless of how Canny is doing, we turn off the “business brain” at the end of the day.”

Andrew

Lesson: Set boundaries and don’t let work take over every conversation. Make space for work and for being a couple.

What makes our relationship work

Our shared vision and values are the core of our relationship.

There are definitely advantages to starting a company with your significant other. Andrew and I already had a foundation of trust before we started Canny. We also knew how to communicate and have disagreements.

Startups aren’t easy. If they were, everyone would start a small business. We’ve seen some co-founder relationships fall apart because of little things. It usually happens because of a lack of trust.

I can’t imagine stressing over ownership percentage, for example, on top of running a business.

At the baseline, we are pretty different people. Still, we share the same morals, beliefs, and goals for the future. This alignment keeps us grounded and focused when dealing with daily tasks or big life decisions. We both know what we’re working towards every day.

Lesson: I’ve already talked about how important trust is but it’s nothing without communication. Understand how each person prefers to communicate. You need to be able to talk to each other about anything. Otherwise, both your personal and business relationship may suffer.

The future

To be honest, the future feels pretty uncertain right now. The economy isn’t great, but we have a great team and exciting plans for Canny.

When I read books or get advice from other founders, it doesn’t hit me until I feel it myself. Nothing replaces your hands-on experience, so welcome it.

Our exit strategy?

We sometimes get asked about our exit strategy. “If Canny blows up, will you cash out?”

We don’t have any plans on cashing out. Our focus is on building a long-lasting and successful business. We want to start offering equity sales every few years to give our team some liquidity. Our heart is in Canny for the long haul.

“I love this company and team we’ve built. We’re planning on operating this company for the long term.”

Andrew

Lesson: Enjoy the journey.

For those starting a business with their significant other

Here are our biggest learnings for entrepreneurial couples contemplating starting a business together.

1. Complementary skills are key. It’s about having strengths that balance each other. People are happier when they get to do what they love too.
2. Prioritize communication. It’s the vital foundation of any relationship. Be clear, open, and honest with each other, especially when disagreements arise.
3. Learn to disagree productively. Not every decision will be unanimous. Disagree and commit, respect each other’s perspectives, and make a joint decision, even if it involves compromise.
4. Balance work and personal life. Set clear boundaries. Find that switch from work mode to play mode. This balance is essential to maintain a healthy relationship outside of work.
5. Support each other through challenges. The path won’t always be smooth. Support each other even more when the business is challenging. Your partnership should be a source of strength in good and challenging times.
6. Celebrate small wins together: Take time to acknowledge and celebrate your successes, no matter how small. These moments of joy can be a significant morale boost on your entrepreneurial journey.

As we reflect on our journey with Canny, one thing is clear: starting a business with your partner is a unique and special experience. It blends the lines between personal and professional life in challenging and rewarding ways.

While it’s not always easy, the journey is worth it. Embrace the challenges, celebrate your successes, and cherish the experience. I wouldn’t have it any other way!

Want to hear more from us? Subscribe to our updates here.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

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The post Starting a startup with your significant other: what it’s really like first appeared on Canny Blog.

The post Starting a startup with your significant other: what it’s really like appeared first on Canny Blog.

We’ve learned a lot about startup hiring since starting Canny. We launched Canny in 2017, and after reaching ramen profitability, began hiring in 2018. 

We discovered that organic growth and deliberate hiring decisions are crucial. Unlike heavily funded companies, bootstrapped companies like Canny don’t feel the same pressures to hire rapidly. We grow our team as our revenue grows. We always keep profitability top of mind.

How we began hiring

Our first hire at Canny was a big step for us. Sarah and I were managing everything ourselves, but we were also quickly getting stretched thin.

“We were starting to feel overwhelmed. From building our product to doing marketing, we split founder time into many areas. Since we were profitable, we started to ask ourselves – how can we best spend our money to grow faster?”

Sarah Hum, co-founder at Canny

At some point, we became so busy that we realized we needed help. Our main duties were demos, customer support, content marketing, and product development. This is a lot for two people. The day-to-day operations were keeping us from focusing on the bigger picture.

On top of that, we didn’t have any experience with sales, support, or marketing. We wanted to bring in experienced people who focus on one thing full-time and do it even better than we could.

We asked ourselves: “What’s the one role that would make the biggest impact right now?”

We landed on content marketing. Many advisors have stressed the long-term importance of content marketing and SEO for SaaS companies. That it takes 6-12 months to really start working. This determined our first hire.

Lessons from the first few hires

Every new team member changed Canny a bit. We learned to look beyond skills. Fitting in with our company culture mattered a lot.

When culture-add team members join, they fit right in. They also hit the ground running right away. This is an awesome feeling for everyone.

Sometimes, things won’t work out – it can be difficult to technically vet for a role that you’ve never done yourself professionally. We learned that take-home assessments are very important. It gives us an idea of the work a candidate will produce and how well they take feedback. For example, today we ask all content marketing candidates to complete a blog post outline and draft. 

We went through lots of challenges, and we view them as lessons. The first time we had to let someone go was extremely difficult but necessary. Going forward, we tried to polish our processes and learn from our mistakes. We are still learning.

Key lesson: don’t rush hiring. Take time to find people who you are confident are great at their job. This may involve a longer hiring process and asking others for help.

Tools and processes we used

We started simple. Online job boards and our network were our go-to. In particular, Hacker News: Who is hiring? and RemoteOK forums came in handy.

As we grew, we adopted tools like Recruitee. It helped us reach more candidates and streamline the hiring process.

Initially, our process was basic:

• Understand what’s bringing in revenue (sales, marketing, advertising, etc)
• Determine what role we need to fill based on that
• Find gaps in the business – where are we stretched thin?
• Make sure we have enough money to hire

As we hired more, we saw the need for structure.

We set up clearer stages in the interview process and defined roles for team members in hiring. It made everything more efficient and fair.

Our team enjoys being involved in hiring – it gives them a sense of ownership. They feel that they have a say in what happens at Canny.

Recently, we hired a head of operations, Clare, who’s now in charge of recruitment. Here’s what she shared about hiring:

“Hiring is a task that many people own at Canny. This means we need to be crystal clear on our ideal candidate from the start.”

Clare Garrity, head of operations at Canny

Key lesson: start with simple tools and grow your process as your startup expands. Emphasize clarity and structure in hiring. Involve your team for a sense of ownership.

Signs for other founders

How do you know when it’s time for you to hire? Most founders try to do it all themselves for way too long. Others hire too early.

Here are a few signs to look out for. They’re good indicators of whether or not it’s time to hire.

Hiring when you need to

Timing is everything in hiring. It’s tempting to build a large team quickly, especially when you see others doing it.

At Canny, we learned to hire in sync with our revenue growth. This means understanding your business’s actual needs and not just hiring to fill perceived gaps.

Ask yourself: “Is this role essential for our next growth phase?” If the answer is no, it might be wise to wait.

Making cost-effective decisions

Bootstrapping teaches you the value of every dollar. We apply this to hiring – we’re strategic about who we hire and when.

It’s not just about salary costs. Factor in the costs of recruitment, training, and onboarding. Sometimes, it’s more cost-effective to outsource certain tasks temporarily or use automation tools until you’re ready for a full-time role. We still hire freelancers and consultants from time to time.

Balancing skills and budget constraints

In a bootstrapped startup, you might not be able to offer top-market salaries. This means getting creative. You can offer equity, flexible work arrangements, and growth opportunities.

Look for candidates who are motivated by the role and your company’s vision as opposed to just a paycheck.

Key lesson: grow the team alongside revenue. Assess the real need for each role. Prioritize strategic, cost-effective hiring decisions over rapid team expansion.

How to drive quality applications and fill roles quickly

We mentioned that rushing through hiring isn’t the best idea. However, taking too long to fill a role might hurt your efficiency. It’s all about balance.

At Canny, attracting a large pool of quality applicants wasn’t an overnight success. It took time, experimentation, and refining our approach. Here’s what we learned.

Create a clear and streamlined hiring process

Admittedly, we haven’t always had a solid process. But we’ve learned along the way.

We have clear stages for our hiring process and assigned owners to each stage. This helps with accountability and efficiency. From the initial application to the final decision, every step is structured. This makes the process smooth for both candidates and our team.

We’re happy to see the results of these efforts now. Today, we publish a listing and get 1,000+ applicants. Recruitee is a great platform that helps – it pushes the listing to Google, Indeed, and LinkedIn. Hacker News: Who is Hiring is another great source of candidates.

This presents a new challenge – going through such a large number of applications. Here’s how we overcome it.

1. A freelancer goes through all applications, filtering out candidates who:

• Don’t have relevant experience
• Didn’t answer the “Why do you want to work at Canny?” question well
• Don’t meet any other requirements we included in the job listing (eg. timezone, experience)

Note: we find that onboarding and initial collaboration are tough outside of North American time zones. That’s why we prioritize them.

2. For some roles, we first schedule an initial screen. For others, we send them the technical assessment right away.

3. Then we schedule 1-2 technical interviews (depending on the role).

4. We progress candidates to the culture interview.

5. We book a final call to present them with an offer and discuss it.

We ask our new hires how the hiring process was for them. Here’s what one of our recent hires shared with us:

“I applied around Christmas time. I didn’t expect to hear back until late January. In the end, Canny got back to me within 10 days – the first company I heard back from. After each stage, I heard back within an hour! The team was lightning-fast with feedback. It felt like they were as excited about me as a candidate as I was for joining Canny!”

Niall Dickin, engineer at Canny

Build a strong employer brand

We quickly realized how our brand affects attracting top candidates. Many people don’t want to work for any company. They want to connect with the brand.

We’ve been consistently showcasing our culture and values through our content. The goal has always been to highlight what makes Canny unique. Sharing our story has always helped with that.

Adapt to economic changes

The economy always plays a role in hiring.

Economic downturns can lead to a larger pool of applicants. But they also bring challenges like budget constraints.

We don’t let economic fluctuations deter our hiring. Instead, we adapted. We only hire when we have the budget for it. Being bootstrapped helps with this. We also try to focus on essential hires that directly contribute to our growth and sustainability.

Key lesson: invest in attracting the right candidates. Use recruitment platforms, community forums, and social media. Showcase your employer brand, and evolve with the market.

Canny’s hiring approach

We’ve spent a lot of time polishing up this process. We wanted to make sure that we’re hiring efficiently, treating candidates fairly, and finding the best culture fit. Here’s how we achieve this.

Setting clear criteria for each stage

Every stage of our interview process has specific criteria for passing or failing. This clarity helps us maintain consistency in our assessments. It also ensures that all candidates are evaluated based on the same standards.

We use Recruitee’s scorecards to set clear passing and failing criteria. This helps everyone involved in hiring.

We want to be fair and transparent throughout the process. It differs from role to role, but here’s how it works:

Screen

This is the 15-30-minute call to get an alignment check. We try to understand where each candidate has been (work-wise) and where they want to go. 

 To assess how it went, we ask ourselves:

• Did this person meet the minimum criteria we set? (experience, skills, etc.)
• Did they answer all the questions thoroughly?
• Can we give them the career opportunity and progression they’re seeking?
• Will they fit in well?
• Do their compensation expectations match what we can offer?
• Will the logistics work out (primarily time zones)?
• Do they care about joining Canny more than just wanting any job?

We place a high emphasis on relevant experience. For most of our roles, we look for candidates who have experience in:

• A similar role
• B2B SaaS companies
• Startup environment

“We work as a team to identify who our ideal candidate is. It’s important to distinguish between the areas of the role a person can learn on the job and what experience we need them to have already.”

Clare Garrity, head of operations at Canny

This is not just about the years in the field. We look for practical skills and knowledge.

“It’s important to hire engineers that can identify an issue’s root causes, not just mask its symptoms.”

Dan Murray, engineer at Canny

Assessment

We design a technical assessment for every role. It’s meant to be a quick take-home assignment that mimics a typical work project at Canny.

For engineering roles, we’ve decided to put the assessment first, before the screen. This helps us remove bias and surface technically able candidates faster.

Candidates can get a sense of what working at Canny feels like. They get a few days to complete it, so they can work at their own pace.

“Canny’s interview process involved a fun and relevant take-home task. This is a rarity when interviewing for software engineer roles.”

Niall Dickin, engineer at Canny

Some companies forego the assessment stage to move faster. We found that, if you design the assessment well, grading it should take only a few minutes. When you can evaluate assessments this fast, you can still consider many candidates. This benefits both you and all the candidates who applied. And everyone gets a taste of collaboration.

Technical skills are a cornerstone of our assessment. This is especially true for engineering roles. 

We seek engineers who think deeply about problems and are committed to sustainable, long-term solutions. We also need people who aren’t afraid to try something they’ve never done before and “fake it till you make it.”

Dan Murray, engineer at Canny

Technical interview(s)

We might schedule one or more technical interviews depending on the role and the candidate. This is a chance for the candidate to dive deeper into their technical knowledge and explain their thought process. We explore areas like:

• Technical knowledge and skills
• Logical and critical thinking
• Creative and effective problem-solving
• Attention to detail
• Adaptability and eagerness to learn and try new things

“It felt less like a test environment and more like pair programming.”

Niall Dickin, engineer at Canny

Culture fit

We put a heavy emphasis on culture fit. So far, we’ve managed to build a team where everyone feels comfortable with each other. We’d like to keep it this way.

“I like to say we’re looking for a culture add, not just a culture fit. Of course, the vibes need to feel right, but I like to see diversity of thought or experience.”

Sarah Hum, co-founder at Canny

Ultimately, we want everyone to enjoy working at Canny. That’s why we assess the culture fit very seriously. 

We select three people to conduct the culture interview. We always have one of the co-founders (usually Sarah) there. Dan, one of our engineers who has been at Canny for 5+ years, is generally there too.

“Most of all, we look for candidates who understand and value the MVP approach. It’s about identifying what is the 20% effort we can invest for 80% of the value. This mindset is crucial in startups – where resources are limited, and efficiency is key.”

Dan Murray, engineer at Canny

The third person is typically someone who wouldn’t work directly with that new hire. We want this person to assess the candidate’s culture fit versus the technical skills at this point.

We focus on things like:

• Are they easy to talk to?
• Do they seem like a well-rounded and interesting person who can add something to the team?
• If we met them outside of work, would we want to spend time with them?
• Will we be comfortable with them during our team retreats?
• Will they be comfortable communicating with our team?
• Do they make a good impression?
• Do they seem like a person who will take the initiative and help others?
• Are they a culture add?

“Some people assume that making it through the technical interviews means you’re basically in. We actually end up rejecting many candidates at the culture stage. That’s how much we value the culture aspect. Several times, it’s the deciding factor between two or more technically solid candidates.”

Sarah Hum, co-founder at Canny

Simon Sinek, a well-known speaker on business leadership, shares similar advice for finding culture fit.

Interviewing can be stressful. We try to make the process as enjoyable and valuable as possible. Our team members seem to think we’re doing a good job with this 🙂 

“This was probably the best interview experience I’ve had with a tech company! And it was a strong selling point for me. It was clear the interviews placed as much emphasis on testing your technical abilities as well as your compatibility within the team. It’s nice to feel valued for more than just how good your code is!”

Niall Dickin, engineer at Canny

Offer

We always schedule a call to present a candidate with an offer. I’ve done every offer call since Canny’s inception and enjoy doing them. Just sending an email with an offer letter feels dry and impersonal. We want our new hires to feel special from the get-go.

During the offer call, we discuss:

• Position, responsibilities, and title
• Compensation (salary, benefits, stock options)
• Work arrangements (remote job, tech setup)
• Perks (retreats, etc)
• Start day
• Any pre-planned time off
• Next steps
• Anything else the candidate wants to cover

Key lesson: assess technical skills of each candidate. Don’t forget about the culture fit. Lots of people underestimate it.

How bootstrapped startup founders can build a great team

Here are some lessons we’ve learned at Canny that can help you on this journey.

Learn from our experience

One of our early challenges was hiring for roles we weren’t familiar with (sales and marketing). If you’re in a similar position, ask others for advice. Ideally, you have a friend who is experienced in sales or is a founder who has run a sales team. They can provide valuable insights and help you avoid common pitfalls.

Hire slow

Don’t rush into hiring decisions. Taking the time to find the right person is crucial.

Letting someone go is painful. It can also disrupt your team and operations. A deliberate approach to hiring pays off in the long run.

Assess your hiring needs carefully

Make sure each role you plan to fill is absolutely necessary and within your budget. Overstaffing can drain your resources. Understaffing can hinder your growth. Balance is key here.

Implement an onboarding process

Canny didn’t have a formal onboarding process for our first few hires. You might not need one either, especially at the very beginning. With time, start thinking about it to drive efficiency.

“Onboarding is one of the most important aspects of the employee experience. It’s a new hire’s first chance to see if what we sold them in the interview process is true. So we take onboarding seriously at Canny.”

Clare Garrity, head of operations at Canny

We use tools like ClickUp to outline goals for the first day and week. This sets new hires up for success and gives them space to ask questions.

“One of the aspects I enjoyed the most during onboarding was the welcome Slack channel. We set it up for every new hire. Everyone on the team asks them a fun question and shares their answer. Sometimes other team members also answer, and you learn a little about everyone.”

Clare Garrity, head of operations at Canny

These small things make a big difference, especially for fully remote teams like Canny.

Be economical and aim for ROI

Before you start spending on recruitment, set ROI criteria. This way, you’ll know what works and what doesn’t. Then, you can adjust your process for the future.

While we are mindful of costs, we don’t compromise on the quality of our hires. We invest in recruitment processes that bring us excellent candidates. This sometimes means spending on effective job boards or tools that bring in higher-quality candidates. As a result, we get skilled candidates who also align with our culture and vision. And we spend less time finding the perfect fit.

We need to be economical but also understand that unfilled roles can have costs. For example, productivity may decrease, existing team members can get overworked, and we may fall behind.

Key lesson: don’t rush with hiring. Make sure you actually need to hire and can afford it.

Hire, but be smart about it

Hiring is a tightrope walk, especially when you’re bootstrapping like we are at Canny. It’s all about finding that perfect balance.

Each phase of our Canny journey has taught us that hiring isn’t just about filling a seat. It’s about finding those gems who will bring something extra to the table.

Our biggest learning: take your time and don’t be afraid to wait for the right fit. Trust us, it’s worth it in the long run.

In short, hire smart, stay true to yourself, and keep building that dream team.

Andrew Rasmussen

Hi, I'm a co-founder of Canny. Before that, I was a software engineer at Facebook. I love JavaScript, rock climbing, nerding out about the future, and SaaS.

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The post Canny’s guide to growing your team at your bootstrapped startup first appeared on Canny Blog.

The post Canny’s guide to growing your team at your bootstrapped startup appeared first on Canny Blog.

Either way, you know the struggles of keeping the culture alive when working remotely. Even the most introverted team members feel isolated. Don’t get us wrong, we prefer and love remote work. However, we know it comes with its challenges.

How do we overcome them? Team retreats.

When your whole team travels together, very special connections form.

Let’s go behind the scenes of our latest team retreat near Toronto. We’ll tell you all about the planning, execution, and lessons we learned from this experience.

After every retreat, we send out a quick survey to see what the team enjoyed and how we can improve. We’ll share quotes from our team members throughout the article.

Follow along!

Why retreats?

Especially if you’re a remote-first company, we highly recommend team retreats. They’re a big investment (of time and money), but the benefits far outweigh the costs.

We’ve been doing team retreats since we hired our first person in 2018. From a 3-person to 16-person company, we’ve always prioritized retreats (except for a break during the pandemic).

Everyone always bonds so much during our retreats. People who typically don’t work together start collaborating. Team members who might otherwise stay quiet come out of their shells. Everyone has a chance to share ideas, speak up, and get involved.

Having fun together outside work helps to form special connections between people. Those connections then boost work relationships. We always feel extra energized and motivated after retreats.

“Remote work is like a long-distance relationship. You don’t see your coworkers for 4-6 months and start missing them. When you finally see each other, you have an awesome time together. That’s what makes these retreats so incredible.”

Andrew Rasmussen, co-founder of Canny

This retreat near Toronto was our 8th retreat. We plan each of these retreats ourselves, with no external help. It’s a lot of work, but we enjoy the process and feel very accomplished at the end.

How we pulled it off

As the team grows, planning needs to become more and more detailed and strategic.

Canny started with just two people—me and Andrew. As the team grew, we planned retreats for up to five people, and it was pretty manageable. Finding affordable accommodations was much easier, and everyone could stay in the same place.

Now that we’re a team of 16, a lot more planning is involved.

We’re lucky to have a very passionate and dedicated team that helps organize. For Canny Cottage, six of us volunteered to help with retreat planning.

Note: we created a Slack channel to get this going. Anyone can join, but everyone who does has to contribute. That’s our only rule: no lurkers! 🙂

We typically start planning the next retreat as soon as the last one is over. Here’s how it goes.

Choosing dates

Personal trips and other commitments often get planned 3-4 months in advance. We lock in the retreat dates early so everyone can block their calendars.

First, we send out a survey to see which dates work for everyone. Usually, we do a spring and a fall retreat. Summer and winter tend to be busier for people, and we try to avoid intruding on anyone’s personal lives. We also want to make sure most people can attend—this maximizes the value we get out of the retreat.

We always plan our retreats to include a weekend so we have full days away from work. From there, we keep things flexible.

During our previous retreat in Japan, the weekend was rainy. Instead of trying to enjoy Japan in the rain, we shifted our schedule. We spent Friday outside and worked on Sunday.

We used the same strategy this time. It works really well! It’s also easier to book most things on weekdays.

Tip: Choose dates early—3-4 months in advance. Ask for everyone’s availability using a survey and optimize for the majority.

Picking a location

Once we find the dates that work, we start brainstorming destinations. Here’s what we consider each time:

• Visa requirements
• Flights and layovers (we have team members in the US, Canada, Spain, and Turkey)
• Accommodations
• Activities and meals
• Safety and security
• Costs for all of the above

In the past, we’d been to Portugal, the Czech Republic, Croatia, the USA, Spain, Mexico, and Japan. Right now, more than half of our team lives in Canada, with six in Toronto. That made picking Ontario an easy choice, especially after a Japan retreat. 

This time, we wanted to focus on accommodations over the destination. We wanted a place where 14 people could comfortably work—both together and independently. Some of us need focused uninterrupted time. Others have to take calls and attend meetings. Our accommodations had to serve both purposes.

We found a luxury lakefront cottage one hour away from Toronto. On top of being a large and beautiful space, it offered lots of cool amenities. We had access to the lake and kayaks, a sauna, multiple hot tubs, and a cold plunge. Indoors, we had a game room, a gym, a movie theater, and lots more.

While the Ontario cottage country isn’t as exotic as Tokyo, we made up for it with an amazing Airbnb.

“The location emphasized to me that the destination isn’t what made it fun. It was the people.”

Adam Laycock, engineer at Canny

All 14 of us couldn’t comfortably fit into one Airbnb, so we rented another smaller one two doors down. This meant everyone could have their own bedroom—almost all had an en suite!

“Accommodations were super baller. They had all the activities to keep us engaged. It was such a comfy stay.”

Alice Wong, sales at Canny

Everyone had enough space to rest, work, and play.

“I loved the accommodations. Something about staying in such a nice space really makes the event.

Some attributes I loved about our place:

• Huge living room and kitchen that can easily fit our whole group
• Great amenities like games room, movie theater, sauna, gym
• Luxurious level of quality”

Andrew Rasmussen, co-founder of Canny

Tip: If you want to encourage brainstorming and collaboration, make sure your accommodations can serve that. Find a place that offers enough room and a variety of spaces. Large shared spaces, some secluded and quiet areas, and, ideally, “fun” spaces as well.

Arranging transportation

We booked flights for out-of-town guests well in advance to get the best prices.

For transit on land, we rented two Chrysler minivans. We coordinated flights and pick-ups in advance to make logistics go smoothly. 

Tips:

1. For best cost-savings, think through transportation logistics ahead of time
2. Don’t plan any group activities for the first day of the retreat
3. Give people time to settle in for the week ahead

Feeding the whole team

This required more planning than usual. Since we didn’t stay in a densely populated city, food options weren’t as readily available.

We started by researching restaurants in the area. Most of the good ones were in a larger town nearby. We wrote down some restaurants and contacted each to see if they needed advance notice for a large order. We also researched delivery options for each. Then, we looked at our activities itinerary and decided which restaurants were on the way to or from those activities. 

We briefly considered getting a private chef, but that turned out to be extremely expensive. Catering options were very limited.

When we weren’t going out, we had to make sure we had enough food at home. Since we were staying in a smaller town (35K population), we decided to cook most of the meals ourselves. After all, we had a fully-equipped kitchen in our Airbnb! This worked out well and gave us more opportunities to bond and collaborate.

We planned for all breakfasts and several lunches to be self-serve. We made a food list and a separate food itinerary in Notion. Here’s what it looked like:

Getting organized in advance simplified shopping. We knew exactly what and how much we needed for each meal. In stores, we picked a category (breakfast, lunch, snacks, drinks, etc) and split up. This made shopping more efficient.

A few team members highlighted the home-cooked meals as one of their favorite parts.

Tip: Get super-organized about food. During the retreat, you’ll be too busy to think about it.

Planning activities

Great activities are a big part of making a retreat memorable, so we put a lot of thought into what we want to do.

Before committing to anything, we asked the team what they were interested in. We actually set up a separate Canny board where team members submitted ideas and voted on existing ones 🙂

You can do the same in Canny, and it’s completely free.

We also purposefully made some of them optional. Our past experience showed that some people like to always be on the go, and others prefer more downtime. We wanted everyone to get what they wanted out of this trip.

We researched, planned, and booked the following in advance:

• Local hockey game
• Curling
• Pumpkin patch visit (pumpkin picking, corn maze, hayride)
• Escape room
• Murder mystery game at home

We reserved plenty of downtime to enjoy our Airbnb and everything it had to offer. That included:

• Jam sessions (we rented musical instruments)
• Halloween decorating and party
• Board games
• Movie nights
• Pumpkin carving
• Numerous sauna, hot tub, and cold plunge sessions

Tip: Some things to consider for activities are:

1. What’s unique to where we’re staying?
2. What festive events might be happening?
3. What kind of energy levels can we expect each day?

The itinerary doesn’t need to be jam-packed—allow for sufficient downtime. This leaves room for spontaneity and space to recharge.

“It was nice to have the emphasis on bonding with the team versus exploring the country (like we did in Japan).”

Niall Dickin, engineer at Canny

Getting work done

Retreats are actually some of our most productive work times. It’s a great chance to collaborate in person. We typically do more high-level strategy meetings.

At the beginning of the retreat, we recommend that leadership does a kickoff. It’s a great way to get everyone aligned and in the same mindset for what’s to come during the week. It’s also a good time to share big plans.

These trips give us a great opportunity to brainstorm together in person. After we go home, we keep that momentum and collaboration going.

To ensure these retreats are productive work-wise, we specify what we want to get done beforehand. This can include:

• Which meetings do we want to hold?
• What specific things do we want to achieve? (complete a project, ship an MVP feature, record a video, etc).
• What ideas do we want to collect? (product features, blog ideas, onboarding initiatives, etc).

Everyone can run a meeting, see how others work, and get involved. We plan meetings in advance and set clear goals and agendas.

“The collaboration was great. It was easy to take action on things quickly.”

Adam Laycock, engineer at Canny

One of our team members, Julia, joined Canny only a week prior to the retreat. This was a great opportunity for her to get to know everyone, shadow others, and bond with the team.

“The collaboration during onboarding was amazing. It provided a great opportunity for us to come together, share insights, and really get to know each other. It was especially helpful in absorbing all the new information.”

Julia Valade, customer success at Canny

On an everyday basis, we sometimes miss a chance to walk up to someone’s desk and pick their brain. This is exactly what retreats like these accomplish.

“Compared to other retreats, this one felt the most productive. I also enjoyed being included in all activities, and I returned home not as tired as from previous retreats.”

Maria Vasserman, content marketing at Canny

The marketing team was able to create lots of content during this retreat. You’ll see some photos and videos pop up on our social media soon. Give us a follow to see them 😉 

• LinkedIn
• Twitter
• Youtube
• Facebook
• Instagram
• Tiktok

Tip: Make sure your team’s leadership thinks about how best to use your time together in person. They should be prepared to run meetings by having goals and an agenda. We always have action items noted down at the end of each meeting.

Hackathon

This activity deserves a special mention. After the kickoff, we brainstormed some ideas that aligned with where we want Canny to go. Then, our developers split into pairs, picked an idea, and got to work. They only had a few days to work on their idea, so the goal was to build scrappy but functional MVPs.

Design and marketing teams assisted engineers—they mocked up designs and planned promotions.

On our last day, each team presented their ideas. This day fell on Halloween, so we presented in costumes.

Our Smart Replies feature was born out of this hackathon.

“The highlight was the hackathon. Not just because we built some cool stuff, but also because it let me work 1:1 with a colleague that I haven’t directly worked with before.”

Ramiro Olivera, engineer at Canny

What we learned

Our biggest goal for these retreats has always been bonding. We prioritize culture, and retreats are a huge part of it.

We believe that we achieved that—many people on the team mentioned bonding as one of their highlights.

Spending a whole week with anybody can be overwhelming, not to mention coworkers. We made a point to strike a balance between work, activities, and relaxing. We feel like this retreat in particular accomplished that.

Throughout the retreat, I ask everyone to take videos in landscape mode. At the end of every retreat, I put together a little video. It’s a great way for us to relive every retreat and the good times we had. The video also gives future teammates a glimpse into what working at Canny is like.

We took note of some things to improve for next time:

• Apply for visas even earlier than we think
• Ask for more help with planning when we need it
• Delegate shopping/cooking responsibilities even more
• Make more activities optional

How you can make your corporate retreat awesome

If you’re sold on team retreat now, that’s great. You’ll get a lot out of it, and your team will definitely thank you. Here are a few pointers to help you make it a success:

1. Survey the team as much as possible in advance. Ask about dates, locations, preferences, dietary restrictions, activity ideas, etc.
2. Plan as early in advance as possible—at least 3-6 months. Think of dates, locations, travel, transportation, visas, schedules, food, activities, and work. We know, it’s a lot.
3. Ask for help from the team when you need it. Don’t try to do everything yourself.
4. Encourage each team member to set a goal for the retreat. This will help keep this productive and worthwhile.
5. Encourage collaboration and participation. Schedule meetings and brainstorms, but also leave time for people to split into groups and do their own thing.
6. Remember: it’s impossible to please everyone. Just do your best!

We hope that you’re now excited to plan your team retreat. We’ll share more about our retreats and team activities, so stay in touch.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

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The post Canny cottage near Toronto: post-retreat reflections first appeared on Canny Blog.

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Design is more than just the “looks.” It’s a key player in a startup’s success. It shapes how users feel and interact with your product. It can set you apart in a sea of options. That’s where a design founder comes into play.

We created Canny to be easy to use and user-focused. Our design-first approach wasn’t just for show – it guided every choice we made. It helped us win users’ hearts, turning quick visits into lasting relationships.

If you’re curious about building a design-first SaaS, keep reading. I’ll share some design principles we live by that helped us get to where we are today.

Canny’s journey and the role of design

Before starting Canny, I ‌worked on the design team for Facebook Messenger. When we started Canny, I knew I wanted to build a product centered around design.

Since building and designing Canny, we’ve received positive feedback, especially around our design.

“It just works. The UX/UI is simple, people have no questions about using it. It’s the kind of product that I really love.”

Aurélien Georget, CPO at Strapi

My focus on design extended beyond just our product. Other high-level areas I always pay special attention to include

• Landing pages (they create the first impression)
• Pricing page
• Product onboarding

Focusing on design might be tough if you don’t have a background in product design. I still believe a few simple design guidelines can go a long way. It’s all about the mindset.

Pre-design: setting the stage

It’s tempting to start working on your big idea right away, but hold on! There’s groundwork we can’t skip.

1. Know your target audience

Understanding your audience is key.

• Who are they?
• What do they need?
• What do they love?

Dive deep into who benefits most from your product. Explore their lives, wants, and dislikes. The more you know, the better you can serve them.

2. Explore different paths

Each problem often has multiple solutions. It’s tempting to go for one of them. Try to top yourself and think:

• Is the issue just a symptom of something bigger?
• Is there a smarter, simpler fix?

You might not need to do any design work in the end.

3. The power of ‘no’

Here’s a hard truth: you can’t do it all. Trying to please everyone pleases no one. You’ve got to pick your battles.

Choose the ideas that pack the most punch. Sometimes, this means turning down suggestions, even good ones. How? Show your work. Use data to explain why one feature wins over another. It’s not personal; it’s strategic.

Check out this fun video we put together about saying “no” to feature requests.

5. Balance it out

Remember: good design is a balancing act. It’s not just about how things look, but how they work. It’s the harmony between form and function, UI and UX. Keep this in mind, and you’re off to a great start.

Now that you have this foundation, let’s dive into some common design principles.

UI meets UX

Design is a dialogue. UI and UX are our key speakers. They might seem similar, but they play different roles in one crucial conversation: the user’s journey.

UI, or user interface, is all about what meets the eye. It’s the buttons you click, the paths you follow, and the visual cues that guide you. UI design needs to be clear and tell users what’s up at a glance.

UX, or user experience, is the big picture. It’s how all the parts come together to make you feel. Is it easy? Is it enjoyable? Does it make sense? UX controls all that.

When UI and UX work in harmony, they create something special: a user-holistic experience. It’s not just about a nice facade or a single fun feature. It’s about a seamless journey from start to finish.

There’s a concept called “dribbblisation of design.” Typically, “things that look great but don’t work well” fall under this category. Great design aims to fix that and help people actually use the product.

Reaching goals

Users don’t like hurdles. They want to reach their goals with no fuss. That’s why we aim to cut the clutter and keep things smooth. That means removing bumps in the road and making sure each step feels natural.

Simplicity

Ever heard of “drunk user testing“? It’s a cheeky way of saying your design should be so simple that anyone could get it, even after a few too many. It’s a funny idea, but it’s got a point. Simple is sticky. It’s what keeps users coming back.

In the end, great design crafts a journey that feels good every step of the way.

At Canny, our goal is to build a product that is a joy to use. We aim to bring users to their “aha moment” as quickly as possible, with minimal distractions. In other words, we try to make it super simple to use. Our customers seem to resonate with our design approach.

“I love the design and single sign-on solution. I also love the fact that Canny is hosted on our domain. And it’s simple. It just works. There’s no headache. It’s just easy to set up, and it saves time.”

Philippe Lehoux, founder at Missive

Design thinking: beyond the surface

When we dive into the world of design, we’re not just playing with aesthetics. We’re engaging in “design thinking” – a creative, strategic approach that starts with understanding people. It’s a philosophy that doesn’t just seek to decorate but to dive deep, explore, and solve real-world problems in intuitive ways. And this mindset is the heartbeat of everything we do at Canny.

Design as a problem-solver

This approach isn’t about impulsive fixes. It’s about useful solutions. It means stepping into the user’s shoes, feeling their pain points, and using these insights to guide our creativity. It’s not about guesswork; it’s about empathy, understanding, and smart, user-centered decision-making.

Intuition is key

An intuitive tool doesn’t just happen. It’s a result of deep understanding and anticipation of user needs. If you do it right, you can predict their needs before they voice their concerns.

It’s design thinking in action — creating experiences that feel natural, almost like the product is reading your mind.

In essence, design thinking takes us beyond superficial beauty. It’s about crafting solutions that resonate on a deeper level.

Here’s how we applied these principles at Canny.

At first, we had a set of default statuses. The options were enough for most customers. Plus, the experience remained simple. 

Years later we added custom statuses. This design process involved:

• Building a status management feature for admins
• Checking how statuses appear in different views
• Updating integrations that involved using statuses

Also, we now need to consider custom statuses for future features we build. It is very easy for complexity to snowball.

In the beginning, we limited our scope to the essentials. It was the right move. From there, we collected feedback to understand how the custom status feature needs to behave.

How can you apply this strategy?

When you’re building your next feature:

1. Strategy: think about your target persona. What goal are they trying to reach? What’s the most optimal/most obvious route to that goal?
2. Engineering: consider building things that allow you to easily expand functionality later.

Remember: adding functionality later is much easier than stripping things down.

Now that we’ve covered some common design principles, let’s talk about applying them.

Navigating design principles

Embarking on the design journey requires a compass, and that’s where solid design principles come into play. It’s not about wandering aimlessly in the creative woods; it’s about navigating with purpose, guided by user research, simplicity, and strategic thinking.

1. Tuning in to user feedback

Listening is an art, especially when it comes to user feedback. It’s not just about collecting opinions; it’s about diving deep into what clients are saying and what they’re not.

Surveys, interviews, and direct questions are your best friends here. They’re the compass needles pointing to the true North of user needs.

2. MVP: The art of essentialism

In the world of product design, MVP (Minimum Viable Product) isn’t about being minimal; it’s about being essential. It’s asking, “What’s the core value we’re delivering?” and stripping away anything that doesn’t scream “yes!”. It’s about avoiding the allure of complexity and embracing the elegance of simplicity.

3. The Pareto Principle: the 80/20 rule

Ever heard of solving 80% of problems with just 20% of effort? That’s the Pareto Principle, and it’s gold. It’s about identifying the most impactful elements of your design and really, truly honing in on them. It’s not about cutting corners; it’s about maximizing positive impact through smart, strategic choices.

4. Simplicity in navigation

Good design is invisible. It’s the silent guide that leads users where they need to go, effortlessly. It’s about sticking to what’s familiar, reducing friction, and making the journey intuitive. Your website isn’t a treasure map; users shouldn’t need clues to navigate.

5. Removing friction

Friction? That’s just a fancy word for “user annoyance,” and it’s a big no-no. Whether it’s a cluttered checkout page or a confusing sign-up form, any hiccup can turn a user’s experience sour.

The goal? Smooth out those bumps. Make the experience so seamless that users glide through without a second thought.

6. Being prescriptive

Choices are great, but too many can lead to decision paralysis. Sometimes, it’s best to guide users down the clearest, simplest path. It’s not about taking control; it’s about enhancing clarity and reducing confusion. Especially in the early days, speed and simplicity win the race.

In essence, navigating design principles isn’t about following a map, It’s about creating the map as you understand the terrain better. It’s a dynamic, responsive process that puts user experience at the heart of every decision. And remember – the journey matters just as much as the destination.

Let’s break this down further.

Simplifying user choices

Every choice is a crossroad, and too many can lead a user astray. That’s why we trim the extras and keep only what serves our journey’s purpose. It’s about presenting options not as a buffet but as a carefully curated menu, handpicked for the user’s delight.

Guiding users with intention

Our designs aren’t just layouts; they’re signposts. Each element is a subtle guide, a nudge in the right direction. We don’t leave a user alone in the dark. We illuminate their path, making the journey not just easy, but also enjoyable.

Focused simplicity

In the battle between simplicity and options, simplicity reigns supreme. Why? Because your brain is a precious resource. We don’t want to overwhelm it; we want to cater to it. Our designs don’t shout; they whisper, providing just the right amount of information at just the right time.

Prioritizing common actions

Not all actions are created equal. We prioritize based on user needs, bringing the most common actions to the forefront. The rest? They’re there, but they don’t crowd the space. They’re like backstage crew, out of sight, but ready when needed.

Intuitive navigation and discovery

Ever felt the thrill of a seamless sign-up or the ease of a hassle-free checkout? That’s prescriptive design at work.

We lay out features so naturally that users find them before they even realize they’re looking.

Prescriptive design isn’t a set of rules; it’s a philosophy. It’s clarity in the midst of chaos, a beacon for users swamped in a sea of choices. It’s how we turn overwhelming possibilities into focused, delightful experiences. Because in the end, design is not about the creator; it’s about the user – the traveler.

Collaborative design: the path to wholeness

Design isn’t a solitary journey; it’s a collaborative expedition. It thrives on diverse perspectives, thrumming in the space between creativity and practicality. Here’s how collaboration shapes our path at Canny.

1. Embracing feedback and collaboration

Great ideas aren’t born in a vacuum; they’re nurtured through collaboration. We listen — to our team, to our users, to everyone willing to share a piece of their mind. Feedback isn’t criticism; it’s the soil where our ideas grow. It challenges us, pushes us, and molds us into better creators.

Listening to feedback helps us create a community out of our users. When we engage in conversations with them, we start to understand their needs and pain points better. 

2. Creativity meets pragmatism

Creativity is the heart of design, but pragmatism is its compass. One pushes the boundaries; the other sets them. It’s a delicate dance, a give-and-take where wild ideas are tempered by real-world constraints. And in this balance we find our truest, most impactful expressions.

3. Cultivating continuous improvement

Design is never finished. It’s an evolving entity, a story that unfolds with each user interaction. We’re not just builders; we’re gardeners, tending to our creations, pruning here, nurturing there. We embrace change, celebrate adaptation, and strive for improvement.

The advantage of a design-driven co-founder

What is it like – to be a designer and a co-founder? It’s like having a secret sauce for your startup. Our design journey with Canny isn’t just about making things look snazzy. It’s about constantly getting into our users’ shoes, really feeling what they feel, and letting that shape everything we build.

This approach turned complexity on its head. We choose clear, simple, and sanity-saving options that our clients can’t get enough of.

And the collaboration? Gold. Nothing beats the buzz of bouncing ideas around and making something better than you’d imagined.

Remember: your knack for design isn’t just a cool skill; it’s your startup’s ace. It’s about creating experiences, forming real connections, and steering your business in a direction that feels right. Own that superpower, and watch it propel your startup to the stars.

If you’re a founder, but not a designer, I hope you can use these tips and principles and build a better product.

Sarah Hum

Hey there, I'm one of the co-founders of Canny. As a founder, I dabble in pretty much everything but my expertise is in product design. Outside work, I enjoy digital illustration, a cappella, and hanging out with our dog, Emmy.

All Posts · Twitter

The post How design can help your startup stand out: tips from a designer founder first appeared on Canny Blog.

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Why retreats?

Our semi-annual retreats have been at the core of Canny since the very beginning. Because we’re all remote, we really need this quality time together. Over the years, we’ve noticed how much closer we all become after spending a week together in an unfamiliar place.

This retreat has been the most logistically challenging one yet.

Preparations

We always start planning our next retreat soon after the previous one is over. So, we started planning for a May retreat in Tokyo in November. We had to consider:

• Visa requirements
• COVID restrictions
• Flights and layovers (we have team members in the US, Canada, Spain, Turkey, and the UK)
• Accommodations for 14 people
• Activities and meals
• Costs for all of the above

So yeah, it was a task and a half. But boy was it worth it! Here’s how we approached it.

How we made it happen

We started by assessing all the costs – of getting there and being there for 9 days. We tracked flights from each location (and scored some sweet deals!) and compared prices for hotels and Airbnbs.

Acommodations

We split the team by departments and booked 2 different Airbnbs (with 5 units in total). Luckily, they were only 5 minutes away from each other. This was very important to scheduling team meetings and hangouts together.

Meals and activities

For meals and activities, we tried to plan in advance. Getting a table for 14 people in a Tokyo restaurant is probably a lot to ask for, so we had to be resourceful.

As soon as we locked down Tokyo as a destination, we created a Canny board for ideas and voting. Yes, we used our own software for retreat planning. 😎

Anyone could submit ideas and vote on them. That’s how we came up with a shortlist of things to do and see.

We also found and saved some highly-rated restaurants (using Google and Tabelog) in advance. Once we were there, we split into smaller groups to find tables easier.

We booked some activities months in advance – teamLab Planets Tokyo, the Ghibli Museum, and Urayasu Ooedo Onsen. Each of them was incredible!

Important: every activity was entirely optional.

Our team is now quite big, so we had to consider everyone’s preferences. It’s very important not to leave anyone out, but also not to force people to do anything they’re uncomfortable with. 

We’re lucky though – our team is usually on the same page, and we all vibe very well together.

Finally, we had a Notion document with some FAQs and important information about Japan. We  wanted to ensure that our team understood the culture and that we were prepared and respectful.

Exploring Tokyo

After all the planning, we finally arrived in Japan. A few of us landed earlier to explore beforehand. And, some of us stayed later to keep exploring.

The team met on May 11 and found our way to Komagome – that’s where we were based for the next 9 days.

We chose this area because it’s:

• Quiet
• Has a subway station
• Has lots of food options
• Close to key attractions

As we waited for everyone to arrive, we got some Japanese snacks from 7-Eleven and just hung out.

During these 9 days, we saw a lot. In particular:

• Inokashira park
• Ghibli museum
• Shibuya
• Akihabara
• Karaoke 2x
• Urayasu Ooedo Onsen
• teamLab Planets Tokyo
• Arcades
• Kamakura
• Cat cafe
• Shinjuku

We got some rainy days, so we swapped weekends and weekdays to make the most out of this trip.

We tried all the Japanese food we could find and made many memories together.

It’s bound to happen: with such a large group, people can get lost and separated. During our team outings, that happened a few times. Don’t worry – we all found each other in the end!

We came up with an idea for next time – ask people to pair up. This way, if someone’s lost, at least they’re not alone.

You can swap buddies each day too – just to mix it up. We’ll try it next time and will report back!

Working

As always, these team retreats are centered around team collaboration. We had several very productive meetings and brainstorming sessions. Anyone could create and lead a meeting too.

We talked about:

• The future of Canny
• Product specifics and direction
• Pricing
• Operations
• Marketing
• And more

Important: we made sure that each meeting had an owner. It’s easy to get lost in brainstorming and not assign any action items. So we did our best to prevent it.

We also created lots of content, taking advantage of being in such an awesome and unfamiliar place.

Lessons

This trip was a truly amazing and one-of-a-kind experience. Everyone took away something unique and special for them. Here are some of the learnings from this trip:

• Plan in advance, as much as possible
• Don’t assume anything – research all prices, accommodations, and unique quirks about your destination
• Involve team members and plan together
• Be flexible and ready for plans to change
• Be ready to split into smaller groups
• Have an open mind and encourage every team member to do the same
• Rest, try to avoid FOMO, and enjoy

One thing’s for sure: we’re all still in awe of Japan and our team. We’re now extra-motivated to work hard and bring our ideas to life. And, of course, we’re looking forward to our next adventure together.

Maria Vasserman

Maria loves all things creative – writing, photography, movies and beyond 🎥 When she's not creating content to tell the world about Canny, she's either photographing a wedding, jumping at a rock concert, camping, travelling, snowboarding, or walking her dog 🐕‍🦺

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The post Canny in Japan: post-retreat reflections + videos & tips for team retreats first appeared on Canny Blog.

The post Canny in Japan: post-retreat reflections + videos & tips for team retreats appeared first on Canny Blog.

Clare Garrity, Operations Lead

Clare has been working in SaaS since 2014, leading operations and people functions at a number of international startups. A lover of questions, she has always been fascinated by the people around her and the processes that exist within businesses. 

Originally from Ontario, Canada, Clare currently lives in Vancouver. In the past, she’s lived and worked in Ireland, the UK, and Australia.

Clare ‌joined Canny to lead our business operations. This includes people ops, compliance, legal, finance, and working with our customer-facing teams. 

Here’s what Clare says about working at Canny:

“Canny is the first role where I can use all of my professional experience every day. I get to strategize, execute, be creative, and work with highly intelligent and motivated people. Everyone on the team gets a lot of trust, autonomy, and support. Canny listens and values everyone’s voice and opinion, and I love that.”

When she’s not working closely with our co-founder, Andrew, on operations, she’s usually walking the Vancouver sea wall with her dog Chico or bringing her imagination to life in some creative way. At the moment, it’s abstract painting.

Sara Al Mouaswas, Developer

Sara grew up in Amman, Jordan, before moving to Toronto to study human biology & psychology. Early in her career, she discovered her passion for software development and has stuck with it ever since.

When she’s not developing the next great Canny feature, Sara’s getting ambushed by her dogs, Plato and Chandler (and occasionally other neighborhood pets), exploring with her fiance, Sina, or going for a swim.

“Besides the amazing team, I love the product! It is really motivating to be building features that were directly requested and voted on by Canny users. Now when I’m going about my daily routine, I start wishing that more tools I love used Canny so I can give the tools’ developers ideas I have, and know that the message will get to them.”

Kaman Hui, Growth Marketer

Kaman was born in Hong Kong and now lives in Canada. She speaks English, Cantonese, and Mandarin.

Kaman loves learning new things and is currently taking a tea sommelier course! She’s learning about teas from all over the world. Soon, she’ll be able to identify tea’s region in a blind test!

Here’s what Kaman says about working at Canny:

“Love the people at Canny! Everyone is so unique yet gets along so well. The team is full of smart cookies and has been great to work with. The culture is also amazing. No ego, open-minded, and flexible. There’s a strong sense of trust in everyone’s work and expertise.”

Niall Dickin, Developer

Niall is the newest addition to our team. He was born and grew up in the UK, exploring all the hiking trails and pubs that the country has to offer. Now he’s moved to Vancouver, Canada, with plans to explore hiking on this side of the planet.

Niall’s always keen to try new things. So far in Vancouver he’s tried outdoor bouldering and a pottery course. He’s planning to add surfing, skydiving, and ice climbing to that list before 2023 is over!

Here’s what Niall says about working at Canny:

Working at Canny is like a breath of fresh air. The people are lovely and are all super smart and switched on, plus the retreat in Japan (which was my 2nd week on the job!) was one of the best trips I’ve ever been on. Best of all, you’re given complete trust and control over your work: you can work around your schedule at times that suit you.”

The Cannisters

We love our small but growing team. From our team retreats to daily Slack conversations, it’s always fun when we’re together.

We’re very lucky to work with such talented and driven people. Here’s to making Canny even greater for all of you!

Maria Vasserman

Maria loves all things creative – writing, photography, movies and beyond 🎥 When she's not creating content to tell the world about Canny, she's either photographing a wedding, jumping at a rock concert, camping, travelling, snowboarding, or walking her dog 🐕‍🦺

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The post Canny year 7: welcoming 4 new cannisters! first appeared on Canny Blog.

The post Canny year 7: welcoming 4 new cannisters! appeared first on Canny Blog.