Top 13 Leadership Lessons from AMA with Amir Salihefendic, CEO of Doist

As the CEO and founder of a bootstrapped, remote company with over 13 million customers, Amir shared his leadership lessons learned with our online community, The Watercooler.

Every few weeks, we invite one of our 1,000+ Watercooler members from all over the world to participate in an “Ask Me Anything” (AMA) session. It’s an opportunity for us fellow managers, executives, and business owners (including me!) to gain in-depth insights on how to be an effective leader.

Last month, we were honored to host Amir Salihefendic, CEO and founder of Doist — the software company responsible for Todoist, a productivity tool used by over 13 million people. Amir’s company is a remote-first, bootstrapped and independent company with ~50 team members from 20 different countries.

Originally from Bosnia, Amir grew up in Denmark, studying Computer Science. Prior to Doist, Amir was part of the founding team of Plurk, a Twitter precursor used by millions of people that to this day, continues to be one of the most popular social networking sites in Asia.

I learned a lot following Amir’s AMA. Here were the top 13 questions and answers….

Question #1

How do your project managers deal with having team members in various time zones? Specifically when it comes to project meetings, sprint planning, demos, client meetings, etc…

Amir: Most of our work happens asynchronously. We used Slack for about two years before we figured out that real-time communication wasn’t a great solution, especially for a remote-first company like ours (we have people in 23 countries, spanning most time zones).

But even for non-remote companies, asynchronous communication can be a great deal. For example, I recently became a new dad, and it’s a huge advantage that I don’t have to be working at any specific times, so I can spend a few hours in the morning with Samuel without worrying about not being at work or affecting work of others.

We do use synchronous communication at times (e.g. Hangout meetings), but our default mode of operation is asynchronous.

I would recommend reading our article that goes much more in depth: Why we’re betting against real-time team messaging

Question #2

I’ve heard companies with remote teams say that remote only works if everyone is remote. Do you share this philosophy?

Amir: I share this philosophy. Remote work (especially as we do it) is an entirely new way of working. For example, we don’t have work hours, we value a lot the written communication, we do very few meetings, and most of the stuff inside the company is transparent and available to everyone (including most numbers such a revenues, daily actives or whatever else).

Question #3

Any advice or thoughts on how to build that team culture and shared sense of purpose from your experience with Doist?

Amir: Great question, Jeremey.

A lot of open-source communities (for example, Python or Linux developers) have incredible cultures, even if most of the work is being done in a remote setting. So I am very unsure if an office environment is needed to build cultures or to build innovation (e.g., Linux has changed the world, and most things run on it).

For us, our culture centers around critical missions that unite us (this is remote-work, productivity, and mindful team communication). There’s also a general feeling that the work we do is relevant and useful to a lot of people. We are also super picky to hire people that have a passion for the stuff we do.

Apart from this, we do have random meetings around the world and a company-wide yearly retreat (which we usually do in some exotic places), but I do think our missions are much more critical than anything else.

It should also be stated that our 5-year employee retention rate is 93% (only three persons have left voluntarily in the last 5 years), so I think it’s possible to build healthy cultures even in entirely remote environments.

Question #4

I know Todoist is bootstrapped and profitable but did you use some of your personal money from Plurk to fund Todoist and build a team or did you go back to full-solo developer mode and slowly got the company into the profitability path?

Amir: I spent very little of my own money. When I went to work full-time on Todoist, it was making a few thousand dollars in revenues per month.

As I increased the revenues, I hired people. The first people that joined had very small salaries (I have no idea of how I convinced them to join :-)).

Question #5

Was it hard to get the product to a point where you were at the same level of quality of tools like Wunderlist, Trello, and Basecamp?

Amir: Competition never drove me. I didn’t know about Wunderlist until very late. I was very ignorant about a lot of things (e.g., I never did market research). This strategy isn’t something I would recommend with my current knowledge 😊

I did lose a ton of time making Plurk, but I also learned a lot of stuff I could use. For example, that I should not raise VC funding and that I should do this in an entirely bootstrapped way. I also became a much better designer and developer, which was also super useful.

What hurt most was that Todoist was built for the web and not mobile. It took us a long time to create super robust mobile apps.

Question #6

How was the decision to work on Todoist after Plurk?

Amir: Todoist was a hobby for me and something I truly cared about. It wasn’t tough to switch to it full time or to imagine working on it for ten years (who doesn’t want to work on their hobby!?)

This said it took me many years to see the real potential of Todoist. I never imagined it would be multi-million dollar business…

Question #7

Are you still involved with engineering and development these days or do you focus all your energy on business and management? And, if you are not so involved anymore, was it hard for you to make the transition?

Amir: I still spend 25% of my time doing development, and I plan to continue to do this. Here’s how I spend my time:

We don’t have any pure managers inside Doist — we expect all of our managers to be doers as well. This works, since we try to hire people that are self-managed and that don’t need a lot of micromanagement.

Development and creating stuff is something I have done since I was 12 years old and I can’t imagine stopping doing this because the general practice is that leaders just need to manage others.

Hope this helped!

Question #8

With a turn-over so small like you mentioned, I imagine that Doist probably figured that out already. I would love to hear what are your thoughts on that and how do keep your individual contributors engaged for so long?

Amir: Like mentioned before in this AMA we don’t have people that just manage other people. This choice is rooted in that we believe that our people should be self-managed and we should do as little micromanagement as possible. We also highly value individual contributors, and the salaries are similar between a fantastic individual contributor and a team leader.

Question #9

How many levels of managers/leaders do you have and how are your departments and teams organized? Do you structure the teams around different products, features, or something else?

Amir: Here’s how our structure looks like:

  • At the top, we have a CEO, COO, and CTO
  • Then we have team heads, e.g., head of Android, head of iOS, head of marketing
  • Rest of the structure is flat (e.g., developer, designer)

We are in the process of adding more roles so people can feel like they are advancing their skills and careers.

We work in dynamic squads in 6 weeks cycles (and we usually do 2–3 weeks of pause between these cycles). A squad could be a designer, a web-dev, an iOS developer and an Android developer trying to improve a specific feature.

Hope this helped 😊

Question #10

I’d love to know how your team comes up with ideas for new features/products and how things get prioritized. Do you have the traditional structure where product/data team comes up with most of the ideas or do you have a different structure?

Amir: Great question!

Anybody in the company can make a DO proposal, and currently, we have 100+ of these. These are ideas of stuff we should be working on. I am attaching an example here:

On each six week cycle we then decide what we should work on using the following process:

  1. The team heads decide on a general theme for each cycle and for each product (could be improving the foundations)
  2. Before each period, each team reviews the DOs and suggests 3 to 5 DOs for the upcoming cycle. They also list massive internal DOs they might be working on (so we can plan better)
  3. I review each team suggestion and compile a DOs RFC, which is shared with everyone, and we can comment and change stuff
  4. We decide a final RFC, and the DO coordinator starts allocating people to DO squads

Question #11

How big is the company and could give a broad percentage of the size of the teams (Engineering, Marketing, Sales, Support, etc)?

We are currently 55 people spread around 23 countries.


  • 26 Developers
  • 9 Support
  • 8 Marketing/Growth
  • 8 Designers
  • 4 Finance/Business dev

It’s notable to know that we don’t have HR or sales. We are currently hiring an HR person tho 👍

Question #12

What’s the one thing you wish you would’ve learned earlier as a leader?

Amir: Doing scheduled 1-on-1s and investing time in making them better. We started to do 1-on-1s very late. I would even recommend them if you are a smaller company.

We use Todoist shared projects for 1-on-1s. Each 1-on-1 has a prepared agenda. We also add actionable tasks that result from the 1-on-1s. This makes our 1-on-1s much more structured and actionable.

Question #13

For many companies (remote or not), hiring is their #1 challenge. What are the key traits you look for when hiring, and how do you structure the hiring process at Doist to account for them?

Amir: We have a HELL YEA rule, inspired by Derek Sivers. When we hire somebody we need either “HELL YEAH!” or “no.” (no “yes” or “maybe it will work”). This simple rule has worked wonders for us.

We’re hiring a programmer

After our best month of sales ever in December, a new spot on our team has opened up…

Dear programmer who cares about doing meaningful work,

If your dream is to grow a product with a small team that already has its legs under them, and have a big impact on a problem that matters, I’ve got some good news for you…we’re hiring a Rails programmer at Know Your Company.

First, a quick introduction.

My name is Claire Lew, and I’m the CEO of Know Your Company. It’s nice to meet you. My company, Know Your Company, is a tool that helps business owners with 25 to 75 employees get to know their employees better. Companies like Airbnb and Kickstarter use Know Your Company each week to improve their company culture.

Our software was originally built by Basecamp (formerly 37signals) in early 2013. Know Your Company ended up becoming so successful as a product, Basecamp decided to spin it off into its own company. In 2014, I became the new CEO of Know Your Company.

Our mission is to help people become happier at work. We believe this happens when people can communicate openly and honestly at work. As the CEO, this is also my own personal mission. I’ve felt the pain of working in a company where Know Your Company didn’t exist. Since then, I’ve made it my life’s work to help others not feel the same way.

So what’s the job?

You’ll be a one-person product team. As our sole programmer, you’ll be responsible for building, improving, and maintaining Know Your Company as a product end-to-end. We’ll riff on feature concepts together, drawing from conversations you and I have had with customers. You’ll uncover the underlying jobs-to-be-done in the situations they’re facing and ensure the concepts we’ve discussed align with our overall vision for the product. Then you’ll take those concepts from sketches to code to production. What you ship will be used by over 12,000+ employees in over 15 different countries every single day.

There’s no project manager, no design team, and no user research team here at Know Your Company. It’s you and me thinking, experimenting, playing detective on how to help CEOs and employees get more out of the product. No marching orders here either — it’s us together deciding what to prioritize, what to focus on, and what to improve.

You will also serve as the primary technical caretaker of Know Your Company. You’ll be our only line of defense when it comes to the stability, reliability, and efficiency of Know Your Company running smoothly.

We’d bring you on first as a contractor, to make sure you enjoy working with us and vice versa. Then if it was a good fit, we’d bring you on full-time. Eventually, we’ll hire another full-time designer for you to work alongside with. As the company grows, we’d continue to build a team around you. And if things worked out well, you would grow into a CTO role.

We recently brought on a Head of Business Development Jess Singer a few months ago. Thanks to her, we just had our record high number of sales in December. With your help, we’re excited to build on that momentum in 2017.

Together, we’d grow Know Your Company to be a tool that improves the lives of hundreds of thousands of CEOs, managers, and employees every day.

Who am I looking for exactly?

I’m looking for someone who works fast and smart. Someone who is a clear thinker and communicator. You write clean, tidy code. While you don’t consider yourself a pure designer, you have an eye for design. You’re always up for learning and becoming better in everything you do.

You know what it means to hustle. It doesn’t matter what you’ve studied (or if you graduated from school at all), or how many jobs you’ve worked at previously. All that matters is what you’ve built. It’s likely you’ve shipped your own product (or several). You might’ve even started your own business (or several!). Throughout your life, you’ve noticed that where other people have failed, you’ve succeeded simply because you stick with things longer than most.

You’re a problem-solver at heart. To you, there’s no greater thrill than building something that helps other people. You love the process of taking an idea that’s just written on a sheet of paper, and turning it into something real and useful. You know what it feels like to be obsessed with what you’re doing…and you can’t wait to feel that again.

You exude humility. You never believe you have all the answers, and are the first to admit when you’ve made a mistake. You’re always eager to teach or explain something in a way that’s simple and friendly to others. In fact, your day is made when you watch someone’s face light up when something “clicks” for them, or when you surprise them by doing a favor that makes her or his life a little easier.

Most importantly, you believe in the vision of Know Your Company. You’ve personally felt the pain of communication breakdowns in the workplace. Or you’ve previously had a boss who you never felt comfortable giving feedback to. Either way, you’re passionate about what Know Your Company stands for, and how we can help as many people as possible become happier in the workplace.

I want to hire the best person for this role — so it doesn’t matter where you’re located. If you’re in Chicago, that’s fantastic. But if not, no worries. I’m open to working with you from anywhere. (Being in a North American timezone is preferred though, given how closely you and I will work together).

I’d love to hear from you.

If you’re interested in working together, please send me an email at Tell me a little bit about yourself, share your personal story, and include any relevant work and links. Writing samples are a plus too.

This is a unique opportunity to shape a product from the first floor and up, and to help solve a significant problem. If you’re the right person for it, I’d be honored if we got to tackle it together.

Looking forward to hearing from you,
-Claire Lew
CEO of Know Your Company

If this doesn’t sound quite like you, but someone you might know, please feel free to pass along this post them! And, I’d really appreciate it if you clicked the ❤️ below too… That way, someone who might be a great fit will see this, too. Thank you!

PS: You might recall us hiring for this role a few years ago. Matt, our original programmer and first employee, served this role incredibly well and recently accepted a position as a partner at another company that his friend runs. We’re thrilled for him! And, even though of course we’re bummed he’s leaving Know Your Company, we are excited that this role has opened up to bring in a fresh perspective. Matt will be sticking around a bit to help around with the transition, and even is pitching in to help screen applicants for us. He, Jess, and I look forward to hopefully meeting you 😊

You need only one good reason to change your business strategy

A big change in business strategy simply needs to never lose sight of just this one thing.

Going through a big change in your business?

We just did at Know Your Company. And what I witnessed is that, as we worked through the change, the reasons to put the brakes on and turn back began to pile up. In fact, it eventually felt as if the scale had tipped against the change.

But we never lost sight of the one good reason we started down this path. And I think this was key to seeing our big change succeed.

After two years of selling Know Your Company via sales demos, it was time to fuel the fire and grow the business. So we decided we were going to offer self-signup and a free trial in place of demos.

We discussed a few reasons to completely change how we sold the product, but above all, we simply believed more people would try and buy the product if they could experience it for free.

Work started in January, and we soon faced challenges greater than in any previous project. And each time a new challenge arose, I felt the scale tip more and more in the direction of scrapping the whole thing.

We needed to revamp our web site to explain how our product works. After weeks of writing, design, and iterations, something didn’t feel right. Know Your Company is as much a methodology as it is a tool, and I wondered if text, screenshots, and video weren’t fit to describe our methodology. Maybe only a personal demo could tell our story well.

Maybe self-signup wasn’t right for us?

We needed to come up with a free trial offering, something we’d never done before. The core question was, how long should the trial last? Right away we experimented by offering a 60-day free trial during sales demos. But results were mixed, and by the time we launched self-signup I was beginning to wonder whether a free trial could actually hurt sales.

Another point against self-signup.

We needed to design and build the onboarding screens for customers to set up their new account. The crux of the design was establishing enough trust with someone that they felt comfortable rolling out our software company-wide. After all, you can’t get to know your company if you don’t include your employees!

Up to this point, we had talked one-on-one with all of our customers during sales demos, so trust was not an issue. A series of web pages with forms and text boxes, on the other hand, looked relatively impersonal. If we couldn’t convince customers to add their employees, we risked a poor experience with our product that’d hurt sales.

The scale was tipping. Self-signup wasn’t looking as hot anymore.

Maybe our product was best sold personally, through one-on-one demos.

Maybe we should scrap self-signup.

But we never seriously entertained this option. Why? Because we felt, even in light of the potential problems, that more people would give Know Your Company a shot if they could try it for free.

That was our one good reason to stay the course.

We launched self-signup in April. Then in June, we had our best month of sales ever. July was solid, and August is shaping up to be a great month too.

Our big change has been a success so far, and things are looking up!

Kudos to Claire, our CEO, for never losing sight of our one good reason.

Of course, we didn’t ignore the issues we encountered while building self-signup. We worked through them. Curious to see how? Give Know Your Company a spin with your business — it’s free to try!