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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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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Now’s the time when everyone starts sharing their amazing accomplishments, their growing numbers, and their big wins. It’s easy to get sucked into this comparison game and feel not so great about yourself.

Turns out that the business world isn’t that much different from the everyday social media world. Someone’s always better, stronger, faster, younger, more agile, and overall more successful. Or, so it seems. This can take a significant toll on our mental health.

Startup founders are built to doubt themselves. No matter how far you’ve come, you’re always comparing yourself to that large and well-known competitor. And suddenly your achievements don’t seem so grand. So here are a few tips on how to break that unhealthy habit and regain your confidence.

Focus on cold hard facts

This will be different for everyone. But try your best not to compare yourself to others blindly. Analyze your numbers (whichever are the most important to you). And then compare them to your own numbers from last year, from the year prior, from year one of your business. Better yet, calculate that growth percentage. Yes, it’s easy to grow 500% at the beginning because you started with nothing. But still – pat yourself on the back for that.

Bottom line: try to outperform your old self.

Moreover, you could be comparing your fourth year to somebody else’s fourteenth year. And that’s clearly not a fair comparison. So, keep that context in mind.

It’s good to look to others for some aspirational routines, but don’t let that bring you anxiety.

Instead, analyze what went right and led to your success. Break down what could have been better and how you can use that as a learning opportunity. Try to document all of that too, and set reminders to refer back to those notes.

Better yet – try to analyze competitors’ wins and, more importantly, fails. You can probably learn a lot from them too and prevent similar mishaps in the future.

Inspire your team

It’s good to be competitive, always challenge the status quo, and reach for the moon. But…not everyone enjoys that. Some creative thinkers will get demotivated very quickly if they feel like they’re never good enough.

Has this ever happened to you?

• You come home from school with an A- only to hear your mum say: “Oh, I wonder why it’s not an A or an A+”?

• Or maybe you come across a social media profile of someone you knew in high school and conclude that they’re much more successful than you (psst: it’s probably not true).

That’s how your team might feel when you set moving targets for them.

It’s OK if you work best this way. Keep at it! But figure out what your team needs and encourage them in the way that works best for them.

One way to combat this feeling of “not good enough” is to set SMART (specific, measurable, achievable, relevant and time-bound) goals. You’ve probably heard this acronym before, and it really does work.

When your goals are SMART, your team can better align on the desired outcome. And then you’ll all know from the beginning what you’re working towards, what success looks like, and what the expectations are.

Improve everyday productivity

Sometimes we get too caught up in our quarterly or even yearly goals (OKRs, KRAs, etc) and lose sight of what’s happening daily. Chances are, you could increase your everyday productivity and see awesome benefits quickly.

Assess how you spend your time on any given day. Is there any wasted time? Once again, don’t beat yourself up. Just set a reasonable expectation for yourself and your team. A never-ending list of items leads to burnout and too many unfinished tasks. So look for balance.

Here are a few productivity tips from Sarah Hum, co-founder at Canny:

• Block off time in your calendar for calls/meetings so the rest of the time can be used for focus
• Prioritize your tasks
• If you’re on the fence about doing something, say no
• Fewer meetings, more async
• Learn how to be good at delegation

Little things like that can lead to very big changes in the long run. Time management is tricky, but it makes all the difference.

Strive for balance, not perfection

Balance is key. If you’re constantly juggling more projects and tasks than you can handle, you’ll eventually burn out. You need to take time to recharge your batteries and enjoy life. 

Remember: your team looks up to you and mimics your work style. If they see that you’re always working after hours and on weekends, they’ll feel obligated to do the same. And that hustle culture can be too much for some people and can lead to people leaving your team.

So encourage a healthy distraction!

At Canny, we have many Slack channels to just chat. We also have random coffee chats every week (a Slack bot pairs us up each Monday). Once every 2 months we have a 90-minute “Team Hangs” call (attendance is always optional!). And we always talk about our weekends and fun things during every call.

These breaks between tasks really help us all unwind and get inspired. Try them out!

Celebrate wins, big and small

You’ve come a long way. No matter where you are right now, you’ve worked hard to reach this level. So did your team. So take a moment to celebrate.

Remember – it’s only natural to feel guilty, “not good enough”, get that imposter syndrome, and everything that comes with it. So acknowledge it. And then put your head down and keep going.

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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$3.5M+ ARR

$0 external funding

2500+ teams using Canny

2022 was a huge year for us. We’ve set super high goals, so we needed lots of support to make it all happen. The best way to do that? Hire great people! So let’s get to know each other.

Austin Boyd, aka Gingie, aka Support Lead

Austin joined us right at the beginning of 2022. He leads our support team (and our cool factor). Don’t believe us? Here are a few facts about Austin:

• Born in California, grew up skating and listening to punk rock
• Opened his own custom leather goods store in California
• Created a tiki bar in his garage
• Played in a band, still writes music and learns all about jazz & blues in his spare time

What did we tell you?

We asked Austin – what’s his favorite thing about Canny? He replied: “Definitely the coworkers! Being able to work in an environment where everyone gets along and is working toward a common goal is definitely the best part. The company culture at Canny is unmatched!”

Eric Hoppe, aka Hop, aka Marketing Lead

Eric joined Canny shortly after Austin as our head of marketing. Since then, a lot more people have found out about Canny 

Eric studied in Hong Kong and now lives in Victoria, BC. He has 5 (!!!) pets with his spouse (3 dogs and 2 cats). Some of these pets professionally compete in various dog sports! Here are some of Eric’s favorite things:

• His spouse and pets
• Coke Zero
• The Midnight (a synthwave band)
• Lego
• The Office
• Dad jokes

“It’s tough to say what my favorite thing about working at Canny is because it’s been awesome overall. But, if pressed, I’d have to say the team. Everyone is incredibly talented, friendly, and great to work with. Makes coming to work each day (virtually) enjoyable, and hanging out in person on retreats is a blast.

Fardeen Chowdhury, aka Closedeen, aka Product Designer

Fardeen got hired because he was wearing his The Midnight sweater while interviewing with Eric. True story.

In all seriousness, Fardeen is an amazing designer who “makes things look as pretty as he is”. OK, this wasn’t serious either.

He hasn’t always been a designer. He actually studied bioinformatics but found his true passion in design.

Aside from work, Fardeen can lift insane weights. He’s also super good at motivating others to do the same. He’s also learning to play the drums (Canny band coming soon!) and loves collecting watches.

We asked Fardeen what he loves about Canny. Here’s what he said.

“I think a lot of what makes Canny great is the team. These are some of the most capable, passionate and skilled individuals I’ve met. They’re also amongst the most pleasant people to spend time with. 

I think the other big factor that makes being at Canny very enjoyable is the fact that it’s bootstrapped. Sarah and Andrew are extremely proactive, diligent and resilient leaders. Their passion is infectious.

All the folks at Canny are also very design-minded. From the engineers to the marketers, everyone cares about quality and wants the product to look amazing and feel even better to use.”

Alice Wong, aka Wongton, aka Head of Growth

Alice is the definition of fun and adventure. She somehow knows everyone, no matter where she is. She gets you into the best club/bar/lounge and lives life to the fullest. She spent the last few years travelling the world, meeting new people, hiking, snowboarding and exploring.

She was born and raised in Toronto in a big family. Her sister is her best friend. Alice is the middle child, which is why, in her own words: “I’m the attention-seeking, loud and naughty one”.

Right now she lives in Fort Lauderdale, FL. And…she’s not sure where she’ll be tomorrow!

Alice says: “I love how we infused feedback into our culture. We built a level of trust where we are always asking each other to chip into ideas.”

Maria Vasserman, aka Masha, aka Content Marketing Manager

Maria got hired because Alice knew her from college. Kidding again! But that was a funny coincidence – the world is actually so small!

She joined to ramp up our content – blogs, social media, videos and everything in between.

On the side, she runs a photography business with her husband. They focus on couples and weddings.

When she’s not taking photos, she’s travelling, snowboarding, biking, hiking, camping and watching good movies. She’s also auditioning for the Canny band soon – as soon as she re-learns the guitar!

“I can’t pick one thing that I love the most about Canny. It’s a combination of:

• The trust I get to own my projects, create and execute our content strategy
• The absolutely amazing, interesting and brilliant co-workers
• Our team retreats of course!

I’ve never felt this motivated, supported and excited.”

Sümeyra Davran, aka Süm, aka Developer

Süm is really embracing “going with the flow” mentality. She doesn’t typically make long-term plans because life is unpredictable. She values people in her life and is happy when she’s around good company. The rest doesn’t matter that much.

Süm is a life-long learner, especially around psychology, space, technology, art, and economy.

When she’s not learning something new, Süm is crafting some hand-made amigurumi, putting together a puzzle, swimming, playing video games, and most likely drinking coffee.

Team Canny

We honestly couldn’t be happier with our team. Every Zoom call feels like a fun hangout with friends. And every brainstorming session is productive, motivating and entertaining. We can’t wait to see who joins us next. We’re actively hiring, so check out our open roles here!

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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Here’s all about our trip, the planning process, and some tips to help you make the most out of your team retreat!

Location

Choosing the location is equally fun and daunting. Researching different places, envisioning our time there, booking accommodations and planning for the trip is definitely fun. But the pressure is also there. We need to consider so many things:

• Flights from 9 different cities around the world
• Visa requirements
• Prices
• Accommodations
• Weather
• Walk score
• Food options
• Activities
• Internet speed and reliability

Mexico City was an awesome choice – it checked all of the boxes. It’s:

• Accessible
• Not too strict with visas
• Affordable
• Offers great accommodation options
• Has generally good weather throughout the year
• Walkable
• Offers great food choices
• Has solid options for activities and things to see
• Reliable internet-wise

Duration

Our retreat lasted 8 days, 7 of which were full days – Thursday to Thursday. 

We strategically planned it to include a weekend. We feel like this was just enough time to fully enjoy the city, get lots of work done, and hang out. We also wanted to ensure the retreat wasn’t too long.

Accommodations 

There were 11 of us on this trip, so we booked two Airbnbs a block away from each other. The key was to book them early. And it worked out really well! Here are some essential things we prioritized:

• Large common area for co-working and in-person meetings
• Fast and reliable internet
• Bedrooms for each team member
• Functional kitchens
• TV to cast presentations on
• Enough bathrooms

Location-wise, we stayed in an area called La Condesa. It’s central enough, so we walked almost everywhere, but it was also quiet enough so that we could chill after long days filled with activities. 

Speaking of which…

Activities

It’s important to plan some activities for the group…but also not to overdo it. If you’re a very active traveler, your first instinct could be to jam-pack the trip with lots of things to do. Alternatively, if you prefer laid-back trips, you might think that you’ll figure it all out once you get there.

The best option, as always, lies in the middle. Here’s our best advice: plan some activities in advance. Get everyone on board and lock them in. But space them out. Those days in between will be a great buffer – some people will make plans on the spot, and others will choose to stay back and relax without feeling the FOMO.

It’s also great to invite activity suggestions from your team. Our team came up with tons of great ideas, and whoever proposed an idea got to take the lead on organizing it. 

Speaking of prioritizing tons of great ideas…we actually created a Canny board to organize our activity ideas and prioritization! Everyone could add ideas and vote on the ideas they liked. It also let us discuss each idea and keep everything organized in one place.

Here are a few things we planned in advance:

• Lucha Libre (day 2)
• Teotihuacan (day 4)
• Escape room (day 6)
• Final team dinner (day 7)

And here are some activities we added on the spot:

• National Museum of Anthropology (day 3)
• Movie night (day 4)
• Go karting (day 5)
• Team lunches & dinners (every day)

If you can, plan a day trip too. 

Teotihuacan was our day trip and it was definitely a highlight of the trip for many of us. We explored the ancient culture of Maya, Mixtec, and Zapotec, caves, tunnels and completed a scavenger hunt throughout the day.

It was nice to spend a whole day on an excursion as a team. Highly recommended!

Tip: check Airbnb experiences for some cool excursions like this one.

Work

Since this is a team retreat, it’s important to make it productive. 

Using your in-person time wisely is vital, especially for a fully-remote team like ours. While we all love remote, asynchronous work, some ideas just flow better when we’re all together. 

Plus, you can do fun stuff like filming videos.

How do you make a team retreat productive? A few ideas:

1. Identify which meetings you want to have
2. Schedule them in advance
3. Plan for them – create an agenda, list of attendees, collaboration document (we used Figma, Google Docs, Notion and more)
4. Decide which content you want to create in advance (i.e. what kind of photos and videos, which format, what equipment you might need, etc.)

Plan for emergencies

Trips are fun, no doubt, but also carry some risk. 

This isn’t meant to scare you though! Just make sure that you prepare. People might get sick or injured, flights may get delayed or canceled, plans will shift, and all of that is OK. 

So try to be aware of that, have back-up plans, alternative arrangements and, of course, a supportive team that will help each other out. Try to be flexible with your schedule and adjust as needed. Also, before the trip, select some decision-makers who will handle these things.

Tip: it’s best if you have someone on the team who speaks the language (we had 3 Spanish speakers) and/or know their way around. If you don’t have that, maybe one of the team members knows someone local?

Enjoy!

Finally, make the most out of your trip. We sure did! We all felt like the work-to-fun ratio was on point this time, so we can’t wait to do this again in six months! Stay tuned for the next post-retreat update.

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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What’s more interesting to us is that behind the scenes, a big part of our growth is due to us moving upmarket.

By upmarket, I’m referring to us selling to bigger and bigger companies. This coincides with bigger and bigger deals. You might recognize a few of the logos we have on our homepage.

We started out selling primarily to small startups. This made a lot of sense while our product was in its infancy. 

As a bootstrapped company with founders specializing in building product, we knew we could build something great. We just had to focus on which features were absolutely necessary.

Since launching our MVP (minimum viable product), we’ve grown the team and expanded the product. As we’re able to offer more functionality and cover more use cases, we can also charge more. 

As Patrick from Price Intelligently mentions, around 30%+ of your revenue should be expansion revenue. While this is a guideline, we understand that effectively monetizing our existing customer base is crucial.

We wanted to share what we’ve kept in mind as we make this move upmarket. I’ll also include recommendations for you if your team is making this move as well.

Continually updating how we market ourselves

The way we market ourselves directly affects what kind of companies will sign up for a Canny trial. We’ve made adjustments and improvements in a few areas:

Homepage

As soon as someone hits our homepage, we need to communicate within seconds that they’re in the right place. We want people who see this page to qualify/disqualify themselves.

We didn’t do a single overhaul of our homepage. It’s all been baby steps, like:

1. Adjusting our language to be clearer and communicate who the product is for. We show what problems we solve and how we solve them.
2. Making it look “professional.” We’re selling B2B SaaS software. So, we designed our homepage to be very straightforward and utilitarian. We removed these cute doodles that made us feel more “startupy.” We wanted our homepage to feel like we are a great solution for big businesses.
3. As we’ve closed bigger and more recognizable customers, we’ve rotated in their logos. This social proof goes a long way for a potential buyer to gain trust and build intrigue. Even better, we aim to have case studies for all of our logos.
4. Encouraging people to book a demo. Larger companies often want a demo of the product. 

Case studies

Putting together customer stories is a lot of effort but it’s very worthwhile. New prospects can read how similar companies are using our software in their own words. 

Of course we sell ourselves, but when others do it for us, it’s much more effective. Case studies are also a great sales tool.

Some of our customers have been happy to provide a case study. With others, we include doing a case study built into their contract. 

We aim to feature customers in a variety of roles, and across different industries.

That way, it’s likely a prospect can find a study relevant to them.

Pricing

Around 20% of people go directly from our homepage to our pricing page. If someone looks at our pricing page and none of the plans seem right for them, they won’t start a trial.

Since the start, we’ve made our buying process self-service and very low touch. We’ve never had a free plan, so from the day we launched, we were charging for the Canny product. 

With our very stripped down MVP, we implemented a 14-day trial (no credit card required upfront), and let people upgrade themselves. 

This worked very well for us and self-serve is still the backbone of our company. I go pretty deep into each of our early pricing changes in this blog post.

As a part of moving upmarket, we’ve set up a custom “Business” plan. This means that packaging and pricing is different per customer. 

Some of our features are only available on the Business plan. This allows us to custom-fit our product to the customer. 

They feel like they’re getting what they need, while we feel like we’re pricing fairly.

Recommendation

Step into the shoes of your ideal customer and evaluate your main landing pages. Better yet, ask ideal customers what they think about your landing pages. 

These pages are your first impression and you want to make sure you get it right. Social proof (logos, case studies, testimonials, etc.) is always great for SaaS.

Figuring out customer support and success

According to ProfitWell, our churn is 50% lower than other SaaS companies of our size.

One of the big pros of moving upmarket is that churn is lower. Contracts are usually annual. and SaaS products, if implemented successfully, become quite sticky.

That said, churn is inevitable, so we go above and beyond to ensure we churn as little as possible.

Onboarding

It’s crucial that we successfully onboard a new customer. We need to make sure they take the steps necessary to get value out of our product.

Ultimately, getting no value equals churn. So how do we manage a successful onboarding?

During the sales process, we get a solid understanding of what they’re trying to achieve. From there we can figure out: Who needs to be involved? What processes need to be put in place?

It’s our job to identify what the best workflows are for our users. We keep our help center up to date to make sure they have the resources they need to set everything up.

For each customer, we know which features they should be using and if they’re using them. Success to us looks like a customer who is getting feedback and utilizing that feedback.

This process can be a lot of effort so I want to mention that we only do this for bigger accounts. We have a great self-serve onboarding process in place for smaller teams. 

Post-onboarding

Once we’ve put new customers on a path to success, we make sure to schedule regular reviews. We go over their activity in Canny and highlight noteworthy usage. 

This is primarily to make sure that they’re continuing to get value out of our product. If they’re not, we figure out what the blockers are and tackle those.

It’s also a chance for us to make sure that they are aware of new features. Adding value over time improves their experience and will make them less likely to churn.

Expanding their usage also gives us leverage to increase their pricing come renewal.

The customer support side is fairly simple. We just make sure that our bigger customers get priority responses.

Recommendation

Figure out a good cadence to do reviews with your biggest customers. It’s a great way to know ahead of time if a customer is a candidate for churn or expansion. 

It’s also a great time to get the feedback you need to make your product even better for them.

Expanding our product

Working with bigger customers means bigger demands. We often get large feature requests to close deals. We are treading carefully here. 

I’ve written about saying no to big customers. Unless a request is popular amongst existing customers or we’re very excited about it as a team, we won’t build it.

What we’ve really appreciated is that we’ve grown as our customers grow. We’ve been able to see how their needs change over time. 

As teams get more customers, more feedback, and become more complex internally, their needs change. Many of the features we’ve released in the last year have been a result of that insight.

Of course, we use Canny ourselves. We can easily slice our feedback to see what our top paying customers are asking for. We also look at what potential customers are asking for. 

We can see how much revenue impact building a specific feature would have. Sales plays a big part in helping product understand what teams upmarket are looking for.

Using our roadmapping feature, we can see where a feature might fit in our roadmap. We look at if we have the time and resources to build a feature.

We prioritize based on our goal metrics and weigh features against each other. I’ve written about how we prioritize here.

For every new feature, there’s a consideration of which pricing tier it will be available for. We’re at the stage where almost all of our features are going into our Growth or Business plans. 

As people see more value in the higher tiers, they can easily upgrade to access more value. A good amount of our increased ARPU has come from people expanding their own usage.

As our product becomes more advanced, our design team makes sure we maintain good UX. We’re very selective about which features we decide to support. 

The last thing we want is to build toggles for every customization people ask for. As the feedback experts, our product needs to be prescriptive and opinionated. 

This is a great way we can ensure our customers find success with Canny.

Recommendation

Keep a close eye on feedback from existing and potential customers. Companies upmarket will tell you what problems they’re running into. 

To move upmarket successfully, you’ll want to tackle the most relevant of these problems.

Figuring out sales

For years, we focused on making Canny a strong inbound engine. Kayla joined Canny earlier this year to head up sales. 

We’re still very much figuring out how to use sales to close large inbound deals and make outbound sales.

So far, what works for us is offering bigger teams personalized demos. Really understanding what problem prospects are looking to solve is key. 

We need to be realistic about if Canny is the right solution for them. It’s in nobody’s best interest to sell something that isn’t a good fit.

The sales process for larger companies is much more complicated. Oftentimes, we need to go through security reviews, legal reviews, and so on. 

There is more policy and paperwork which can add a significant amount of overhead to a deal. We’ve been burned before and have since learned how to protect ourselves better.

At this time, we’re not taking sales metrics too seriously. We want to see what works before turning it into a numbers game.

Recommendation

Ask all the questions you need upfront. You need to have a clear idea of what you’re agreeing to or you’ll waste a lot of time.

Understand what a prospect will need from you and price accordingly. Be very clear about what they’re getting in the quote. 

That way, if changes need to be made, the adjustment in pricing makes sense. You don’t want your prospect to feel you are backing out of a promise.

What’s next?

We have a long way to go and a lot more to learn. We’re finding success slowly moving upmarket and will continue on that path.

If we were venture-backed, we might be compelled to focus on big companies. However, we love our bootstrapped roots and want to support early-stage companies. We won’t be giving up providing Canny to small businesses.

To do that successfully, we have always put an emphasis on design. Canny should be a great user experience whether you’re on our Starter or Business plans.

Additionally, new pricing is something we’ve wanted to tackle for a long time. A pricing change is something that could change the trajectory of our business. 

That said, we want to be very mindful of this change and how it impacts everyone (current customers, our sales team, our support team, and so on).

If you are a past, current, or future customer, we thank you for being part of our journey! We learning a lot and hope to share more down the road.

Onwards to the next million!

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 How we’re moving our SaaS upmarket to enterprise sales first appeared on Canny Blog.

The post How we’re moving our SaaS upmarket to enterprise sales appeared first on Canny Blog.

Of course, that’s easier said than done. Competition for great talent is fierce.

Our small, bootstrapped startup is going up against tech giants for rockstar people. In some ways, they can offer a lot more than us.

Sometimes, it seems almost impossible for us to win. Andrew and I fell for it too by joining Facebook straight out of school. The allure is definitely there.

However, there are several things about Canny that give us an edge over large corps. They are valuable enough that we’ve built up a team of awesome people. All these people could have easily joined a big company.

We asked each of them why they decided to join Canny instead. Here are the main reasons they mentioned. If these qualities resonate with you and your lifestyle, we want to hear from you. Our open positions are listed on our careers page.

Work remotely

We built Canny as a remote company since day one. We knew we didn’t want an office. Neither of us resonated with having a traditional go-into-the-office desk job again. We also didn’t want to be limited to hiring in a specific area.

Working remotely means more flexibility for our whole team.

Canny gave me the freedom and the support to move to a different country.

Ramiro

Work where you want

I used to commute 1.5 hours to and from work. If you like working from home, work from home. I like working from coffee shops sometimes.

Remote work means you can work from where you feel most productive that day. Save that commute time and spend it on more important things. 

Goodbye rush hour traffic, hello sweatpants. 

Work when you want

Not everyone is at their peak productivity from 9am to 5pm. Other than during meetings, your time is yours. If you would rather work at night than during the day, that’s your prerogative.

There are some days when I wake up at 5am and do all my work by noon, and then there are days where I hit the snooze button until 1pm and do my best work at midnight.

Elen

Many people have kids and errands to take care of. Remote work means you take back ownership of your schedule. If you need to go walk the dog, go for it!

At Canny, I’m trusted. I’m trusted to get my work done, to pick the tools I need, to work in the way I work best. I don’t feel ‘managed.’ I feel led.

Jacques

People often talk about time as their most valuable resource. What would you do with more time?

As an engineer, a big selling point is that engineering time is used efficiently. We’re building a tool that listens to customer feedback, so we actually build things that our customers want.

 

And, with a more efficient schedule, I can invest more time into other interests. I’m proud to be involved with Canny’s mission, but I’m also proud of my own interests in relationship building, music production and software.

Dan

Benefits aside, remote work isn’t for everyone. You need to be highly self-motivated and in complete control of your productivity. If you have that, remote work can be glorious.

It was not an option for me to join a non-remote company. The reason for that is simple—working from home gives me the flexibility I need to be at my most productive.

Elen

Team retreats

Our team is currently spread across the world.

While we love working remotely, we also make it a point to see each other in person. A former coworker of Elen’s once said, “Relationships are built in person, and maintained online,” and we take that to heart. 

Our team retreats are for team bonding. We try to get together twice a year. We pick a destination and all fly over to hang out for a week—all expenses paid. Our retreats so far have been to Lisbon, Split, Prague, Denver, and Barcelona.

Here’s a video showing some highlights of our adventures in Spain:

During the day, we work. We prioritize the things we need to discuss with others. We’ve also done a hackathon which is a fun way to get everyone involved with the same thing.

Retreats pack a year’s worth of social interaction into a week. They bring the team together more than everyday office interactions ever could.

Eric

By night, we play. It’s amazing how much you gain from just hanging out in person. We explore the city together by checking out local spots and eating local food. We’ve conquered escape rooms and have gone on day trips via scooter.

I’ve come back from every single one of them with literal jaw cramps from laughing too much.

Elen

Good things happen when you have great people all together in a new city. It’s by meeting in person that we really see how well we get along and learn about each other outside of work. Our retreats have definitely brought us closer.

Company trajectory

Of course, we can’t ignore the financial side of things. Joining a startup is a risk. You want to make sure you’re placing your bet on a winning team.

The first thing that caught my eye was the very small team versus what they’d accomplished already. Four employees? Yet completely bootstrapped, profitable, and steadily growing? Clearly the people behind the product had to be incredibly smart, hard working, and devoted. Sign me up.

Elen

We launched just over four years ago, and we’re making $1.8m per year in annual recurring revenue, 20% of which is profit. What’s more, we’re growing 80 to 100% annually.

All of our offers come with equity. Since we don’t have investors, we give more to the people actually working on Canny. We want everyone on the team to feel ownership over what we’re putting our hearts into everyday. By giving you a piece of the pie, you are more motivated to make it the best it can be.

Venture-backed startups are also an option. A risk with venture-backed companies is your equity could be worthless due to liquidation preference. If a VC-backed company sells for $100m, you could get $0. If Canny sells for $100m, you will get whatever % you own. We believe this is fair, and how startups should work.

Some venture-backed startups also can’t offer a stable salary. Sometimes, they need to rely on another round of funding to continue paying everyone. That is a tricky situation and one we wouldn’t like to be in.

Canny is bootstrapped, profitable, and growing. That means we make enough money to cover our operating costs every month. We answer to nobody but ourselves and our customers. We are in full control of the money we spend and the product that we’re building.

I love working at Canny because I have the freedom to do my work and be creative about it. I get direction when I ask, but have autonomy to do my work.

I love that we are bootstrapped and can make decisions that are best for our customers without having to report to a board. I love how everyone is always so excited and positive. 

Kayla

Startup experience

At the beginning of my career, I thought working at Facebook would prepare me for starting my own company. The truth is, nothing will really prepare you for that except for working at a startup.

If you want to start your own company someday, joining a startup is advantageous. Startups do things differently than large enterprises. People wear more hats so you’re involved in more things.

As Canny grows, I get to face new and interesting technical challenges. This means that as the company grows, I grow with it. And I love it.

 Ramiro

Large companies have their product offerings figured out. As a startup, we’re still experimenting with a lot of things. It’s more about taking risks than making small optimizations. You have the opportunity to learn what it means to build a valuable product from the ground up.

Being bootstrapped allows us to focus 100% on customer feedback—no VC or “higher up” pressure. I’d like to create my own product someday and working at Canny has taught me a lot about how to build a valuable product.

Dan

At Canny, you also have the chance to try things outside your expertise. At large companies, they have dedicated people for every specialized role. If you’re an engineer who wants to write, why not?

We can take more risks. We can iterate on things quickly and easily backtrack in the worst case. We don’t have any investors to please. Your potential for impact at a startup is much higher.

We hear about people’s distaste for company politics all the time. People stepping over you to climb the ladder. Having to go through endless numbers of people to get approval for projects. You name it. At Canny, everything is a simple conversation so most of our time is dedicated to execution.

We’re looking for people who like to try new things. They can adapt to new problems and environments. They also take initiative and speak up when we could be doing something better. At an established corporation, you’re a cog in the machine. At a startup, you’re building the machine.

There are a lot of great challenges to overcome and great problems to solve. I don’t do mundane stuff, and I learn something new every single day. The learning opportunities and the level of satisfaction I get from what I do is super high.

Mert

We’re looking for people who are excited to join a small team. They want to have a big impact on where we go as a company.

Our team

Last but definitely not least, our team. Our product is nothing without the stellar team behind it. Our success depends on how well this team works together.

Hiring was a huge step for us. I’ll be honest, I was nervous in the beginning. The thought of trusting other people (basically strangers) with our company was crazy.

Turns out, we must be great judges of brains and character because we love our team! We managed to find and convince highly qualified people from all over the world to join our growing startup.

The team is amazing. I feel like I’m working with some of the smartest people in the world. They always help me out when I’m stuck or need some backup. Everybody puts in effort to help their teammates when it is necessary.

 Mert

As a remote team, it’s even more important that we invest time in our inter-team relationships. We know about each other’s families, hobbies, and quirks. We speak up when things need to be said, good or bad.

I find it incredible that even though we’re all very different people, we gel with each other like nobody’s business. I feel like there’s an alignment between us that reaches beyond just work.

Elen

The people at Canny are what make it a joy to work here. I don’t just have colleagues, I have actual friends!

 Jacques

Need I say more?

I don’t want to spoil too much, so I’ll end off here. If you like what you’ve read, let us know. We’re always looking to add more rockstar people to the team.

Check out our open roles on our careers page. If you have any questions, send us a message. We’d love to hear from you.

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 Why work at Canny first appeared on Canny Blog.

The post Why work at Canny appeared first on Canny Blog.