Kevin Kirkpatrick, CEO of We Work Remotely, on staying true to a vision and trusting your team

Kevin Kirkpatrick is the CEO of We Work Remotely, a platform to find and list remote jobs. With over 4.5 million visitors, it connects the largest remote work community in the world.

Like We Work Remotely (that was founded back in 2011), Kevin was a remote work fan before it was cool. Much of his career was spent working remotely: he started in consulting, which led to scaling software for Deloitte Digital, which led him back to consulting, before he founded a company, sold it, and got hooked on startups—Kevin is a “get stuff done” kinda guy.

When he was approached with the opportunity to lead We Work Remotely, he’d spent years working in flexible setups and managing remote teams, and was excited to think about the future of work.

“A lot of companies have taken to remote work as an opportunity to increase revenue and decrease costs, instead of an opportunity to foster a new way of working or a new way of living. At We Work Remotely, we're really trying to stay true to our core values of treating remote work less like a checkbox.”

Over the last three years, remote work has shifted from something with potential to be a global phenomenon, creating an influx of remote-specific job sites. But We Work Remotely has been resilient in the face of new competition because the company understands the nuance of remote work like no other.

“Remote” means something different for every company and every employee, and that’s not something a quick “remote” checkbox on a job search can encapsulate. With years of experience working remotely themselves, the team understood that not all remote work is created equal and that investing in clarity and transparency was the key to fulfilling their mission: helping candidates and employers find the best fit.

“We’re a really lean, values-driven organization. We get to focus on this incredibly impactful mission that is bigger than us as individuals or even us as a team.”

Kevin believes that mission, vision, and values are at the core of guiding an organization through anything from everyday challenges to a global shift in the industry—but it’s critical that the team creates those values together.

Every two weeks, during sprint check-ins, they review the mission, vision, and values as a reminder of how they operate and how they need to approach problems. As much as this exercise contributes to a healthy culture, it’s also a management tool that helps direct the team without micro-managing their ideas.

“We hire people who are smarter than us to do things we’re not good at. And then, leaders or managers will often try to get right in there and say, ‘here’s how to do it.’ There’s a big difference between coaching and controlling.”

To Kevin, one of the most dangerous pitfalls of management is to believe that, as a leader, you should be directly involved in every component, overseeing every detail of what’s happening. But inevitably, that causes you to lose focus on moving the business forward and thinking strategically.

This pitfall is avoidable. By setting the foundation of a shared mission and values, Kevin can get out of the way of his team and contribute more meaningfully behind the scenes knowing everyone has the same end-vision.

Ultimately, the key to his leadership of a lean, focused, remote organization is letting go of the desire to control, taking a step back—no matter how counterintuitive it might feel—and giving his team the space to do their best work.

“The thing that I enjoy most about being a leader of any company is finding great people and helping them succeed. I'm just a firm believer that you're really only as good as the team you have.”

Q&A Corner

Q: What does your daily workflow look like? 

A: I actually try to keep it highly varied. But consistently, I'll try to block off time for the things that I like to have on a regular basis or I want to be disciplined about. That might be exercising (which I think is super important for mental health, especially for remote work), spending time writing and getting thoughts out with no structure, or even just getting time outside. I find that I do my worst work when I'm not exercising, writing, or being outside. So I always make time for those things. Being a CEO, the hours can be varied as we have a global team. I'm used to taking calls in the morning or at night. But I still make sure to block off time to do family dinners and have that time and space to myself.

Q: What's something you do to boost your productivity? Any app recommendations?

A: I use a ton of tools. And there's one that I’ve pretty much never stopped recommending. It's called Sunsama. It's a productivity app that I use to run most of my day, whether it's to-dos or planning or just scheduling things throughout the day. Clockwise is another tool I use to strategically block focus time on my calendar.

And then a tool I've been using for a little while now, that I've found incredibly valuable, is called Missive. It's an email client, but I use it with my team as well as with my partner so that we can collaborate on different email threads.

Q: Do you attribute your success thus far to hard work or luck?

A: Honestly, I think it's a mix of both. I think we're conditioned to believe that only one of those answers is honestly acceptable, that everything is hard work—you know, pull myself up by my bootstraps and make it on my own. But I've been lucky to work with great people who have made me better. That has nothing to do with how hard I work.

Whether it's mentors, colleagues, friends, or even family, the people in your life have a major impact on how you see the world and how you think. And I’m lucky to have been in an environment where creativity has been fostered, and where I've been given the room to grow and learn along the way. Those are things that, no matter how hard I worked, I couldn't necessarily have controlled. But I also think that you do have to mix in a good amount of hard work and just be thankful that you can keep trying to do your best work every day.

Q: What's a piece of advice that you have for an aspiring leader?

A: Don't try to follow someone else's playbook. It's really good to look at what other people are doing and try to learn from that, but don't try to copy it. I made that mistake early in my career of thinking, “I think this person's got it figured out, I'll do what they do, and therefore I will become what they become.”

In reality, everyone's learning as they go. And so the people you think have it figured out often don't necessarily have it figured out or if they do, it's what works for them. Part of being a good leader, or even just a good teammate, is knowing what works for you. That requires being honest about your strengths and weaknesses and figuring out how to work with those.