Pioneer Profile: Meet Chase Warrington

4th Oct 2023

It’s time that we recognise the people behind the evolving world of work. Our working lives have shifted to being more inclusive, more people-centric, more flexible, and just plain better for both employees and companies. 

These changes didn’t just happen: they were put into place and upheld by individuals and teams working to create a better working future for everyone. 

So we’re finally putting the spotlight on the people who make great companies great: the people-people.  

People-people are crucial to the success of every company. They find you the talent that drives you forwards, and they’ve taken on an increasingly strategic role in the past few years – often taking on responsibility for mental health, diversity and inclusion, culture, EVPs, Employer Branding and team happiness. 

Read more about the Pioneers List and go behind the scenes to understand how and why we’ve selected our Pioneers.

We were lucky enough to speak with Chase Warrington, Head of Remote at Doist about his career, his experiences with flexible working and building great company cultures, and his hopes for the future of work. 

Let’s dig in! 

Tell us a little bit about your career history, and how you got to where you are now. What were the key milestones?

Thank you for having me, it’s a pleasure to be here. My name is Chase Warrington and I’m the Head of Remote at Doist 👋   I am based in Spain, as one of our 100+ team members who are fully distributed across 35+ countries globally.

In college, I used to dream about working and living full-time in another country. Aside from taking internships abroad, I never thought that dream would be a reality. When I graduated, I sought out a remote job back in 2008, trying to buy myself some time before needing to work from a cubicle every day. I was hired by a hybrid organisation as one of their few remote employees and travelled domestically as part of my job. That satisfied my desire for travel, but only for a little while. I soon realised what I really needed was complete location independence so I left my job to travel, helping my wife here and there with her e-commerce business while we lived all over the world. I guess you could say we were digital nomads before it was cool 😎

In time, I began to look for more work options that allowed me to live and work, fully remote. I came across an open position at Doist and during the interview process, I was blown away to learn the team had always worked remotely and asynchronously. This was unheard of at the time. I took the job leading the international marketing team in 2016 and the remote, fluid workplace was everything I’d been looking for. Working remotely, I can change my environment based on my need for creativity, sunlight, or energy. 

Now, as Head of Remote at Doist, I am living full-time in Spain and charged with improving the company’s remote work infrastructure. Each day, I am managing asynchronous communication, researching new technology that can better support the team, and finding new ways to humanise remote work. 

I’m so lucky. It’s been like a dream for me—I've been living in Spain now for over five years. Because of that, I've met people from all around the world and been able to call a new country home. But, remote work isn’t just about taking your laptop and going to cool places. It’s about crafting what’s great for you and your life.

When did you become interested in flexible working, EVPs and the future of work?

I have always been somewhat obsessed with travel, new cultures, and adventure, so flexible working wasn’t optional—it was a requirement. 

One of the reasons I’m really passionate about remote working at scale is that I had to make so many sacrifices early in my career-—in pay, career progression-—because I wasn’t going to an office. I don’t think that needs to be the case in the future of work. I want to push remote work forward, so others don’t have to make the same sacrifices. A huge part of my job is evangelism and helping others be intentional with their workday, carving a path for others.

What's the most impactful change you’ve overseen?

Our 15+ years of being a remote-first company have taught us that building products remotely hinges upon two crucial cornerstones: effective communication and independence. Coincidentally, those are two of our company’s Core Values

At Doist, very few days go by where I don’t hear or read one of the phrases below mentioned. They truly are core to our company culture, and baking them into how we communicate has a real impact on how we make remote work, work.

1️⃣ Async not asap. We value thoughtful, well-considered work over speedy, one-line-at-a-time communication. By embracing asynchronous communication, we empower our team members to collaborate effectively without the constant pressure of immediacy.

2️⃣ Disagree and commit. Diverse perspectives are our strength. We encourage healthy debates, but once a decision is made, we commit as a team. It's about unity in action, even when we hold differing views.

3️⃣ Remote first, not remote only. Flexibility is key! We prioritise remote work but maintain the option for intentionally curated in-person interactions a few times per year.

4️⃣ If it’s not a hell yea, it’s a no. There are a lot of good ideas, but if everything is a priority, then nothing is a priority. We believe in focusing on what truly matters, so if a project or idea doesn't align perfectly with our goals, we owe it to everyone on the team to pass, even if the potential outcome is positive.

5️⃣ Decisions drive action. We don't dwell in analysis paralysis. Once we make a decision, we act on it promptly, ensuring our ideas turn into impactful outcomes.

6️⃣ Radical Candour. Honest and caring feedback can be especially difficult to elicit in a predominantly async-first environment since non-verbal communication represents 80% of how we express ourselves (and we lose a lot of that in the virtual world). So it’s imperative we foster an environment where open, direct communication is valued, and where constructive criticism leads to personal and professional development.

7️⃣ Deep work. We champion deep, focused work, and we value creating dedicated time for meaningful tasks, while minimising distractions and interruptions, to maximise productivity. Chatting isn't working, being present doesn't equate to output. 

8️⃣ Document it. Knowledge sharing is key in a remote environment, so we make it a point to document our processes, decisions, and insights so that everyone can access and benefit from our collective wisdom. When something is mentioned in passing, we’ll often say “document it”, to ensure it is hardcoded into our employee handbook.

What’s the biggest challenge of being in your role right now?

  1. Hybrid work is often mislabeled as the best of both worlds, but in fact, if not done with a lot of intentionality, it can be the worst of both worlds. Failing to put enough effort into curating an equitable workspace that is optimised for individuals in the office and those working from a distance will not only cause a rift of have and have nots in the office but it will also lead to an emphasis on tools and workflows that are not efficiently implemented for either subset of employees. Not ideal.
    *Note this is not a problem Doist faces as a remote-first company, but something worth mentioning as I see it as the biggest challenge across this space at the moment. 
  2. Documentation is a key component of any distributed team, and at the same time, something that most future of work leaders feel is still yet to be solved. Challenges related to peer-review, obsolete documents and procedures, discoverability, document formatting, and assignment of responsibility are all areas to improve on.
  3. Using synchronous time as a powerful tool. Doist is an async-first team, so we are optimised in every way to operate asynchronously. But async-first doesn’t mean async-only. We’re aware that real-time meetings can be a powerful tool to move the needle at times. Transitioning to synchronous meetings and doing them at a high-level is a challenge we face since we don’t get much practice. Investing in being great at something you only do occasionally can be tough to prioritise.

What do you think the next big trend is in working culture?

The infrastructure around remote work from the standpoint of hiring, taxes, insurance, benefits, etc. 

At one time it was seen as a huge hurdle to overcome to hire from abroad in a fully legal and compliant way - for the employee and employer - and this is changing very quickly. Employers of Record (EORs) are stepping in to solve this, and governments are taking it seriously now that such a large percentage of the global workforce can access employment from anywhere in the world. EORs and the surrounding ecosystem enabling global hiring and mobility will evolve quite a bit over the next few years. 

Similarly, employees will also start to demand access to health insurance, benefits, and other perks that previously would have been sacrificed in favour of workplace flexibility. As that flexibility becomes commoditised, those expectations will change and employers will need to provide the solutions to meet that demand. Fortunately, like EORs, companies are stepping up to solve these problems. 

A second area I’ll mention will be around AI, of course. Remote teams spend an exorbitant amount of time planning initiatives asynchronously, and often struggle with creating accountability, and executing on time. AI could help reduce that friction significantly. With better optimised planning and more timely execution, some of the challenges associated with remote work might be mitigated. 

Chase Warrington is the Head of Remote at Doist, the remote- and async-first company behind the world’s most beloved productivity app, Todoist (with nearly 40M users), and Twist, a collaboration app made for async-first teams

Take a look at the other Pioneers who made the list, and subscribe to our newsletter to get updates on new Pioneers, guides to help you navigate your strategic role, and exclusive invites to webinars and events.