Startup Grind
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Startup Grind

What We’ve Learned Building a Remote Culture

One of the best decisions we’ve made at Help Scout is to build a remote culture.

Remote company culture.

There are a number of reasons why I’m passionate about remote work, but the most important reason is talent. What’s most exciting to me in life is working with people who are a lot better than me and who force me to learn at a high rate. I can’t get enough of it, which is why I’m so fiercely committed to this way of working.

Think of it this way: Do you think more talent exists within a 20-mile radius of your office, or on planet earth?

Like a lot of other small businesses, Help Scout is in a market surrounded by companies with more influence, more people, and much greater resources.

‘Remote first’ or don’t bother.

I’m not a hard-liner who believes remote is the way every business should work. Let’s be honest: Each way of working (remote, co-located, multi-office or mixed) has pros and cons you need to be mindful of. It’s less about the philosophy and more about how well you can execute it.

What needs to change for a company to be remote-first? I could write a whole separate essay on this, but here are some of the key high-level tactics:

  • Managers have to work hard to build and maintain great relationships with their teams. It’s a lot harder being a manager in a remote culture than it is in a co-located one.
  • Most information needs to be written or recorded, available for people to consume it on their own time.
  • You’ll have to adopt a level of transparency that feels uncomfortable at first, so everyone feels connected with the business.
  • Overcome the “water cooler gap,” where people build strong working relationships through shared bonding, by forcing it with a number of strategies.
  • Most of your communication is written and you must be excellent at it. People who aren’t excellent written communicators will struggle on remote teams.

Hiring for remote teams

When Jared, Denny and I founded Help Scout, none of us had ever hired anyone. Ever. And it showed. Not only did we have a lot to learn about hiring, we also took too long to recognize a misalignment and part ways with people.

Seek people in love with the work

The two things I look for when hiring for our remote team are:

  1. a love for the craft.

Optimize for work-life harmony

Remote work skeptics often assume people work less when they aren’t going into an office. My experience has been quite the opposite. When you hire people who love the work, they might end up doing it for 12–14 hours before they even realize it.

What if potential hires haven’t worked remotely before?

I’ve talked with a lot of companies who aren’t interested in hiring remote folks unless they’ve worked remotely before. I don’t understand that train of thought.

How to hire remotely

As a result of our early hiring mistakes, we’ve put countless hours into refining the hiring process. Not surprisingly, as we got more thoughtful and structured, we made fewer mistakes.

Make remote part of your brand

From January through April 2018, 2,898 people applied for roles at Help Scout. Of that group, we hired 11, which is a 0.38% acceptance rate. For comparison, Harvard accepts 6% of applicants, and Google hires 0.2% of applicants.

Change the hiring process

When I lived in Boston, I noticed that a talented person would be on the market for a matter of days before being scooped up. It’s incredibly competitive, and in my experience, it’s easy to make mistakes when hiring this quickly.

A longer hiring process is also a wonderful candidate experience.

It gives both sides a lot of time to carefully consider whether this is a perfect fit, and it gives the candidate the chance to get to know several people on the team.

Recruit to diversify the hiring pool

The data is abundantly clear: Diverse companies are more successful. As noted in our first Diversity and Inclusion report (we’ve made significant progress since then that we’ll share soon), we do proactive recruiting to even out the hiring pool.

Investing in remote team culture

Remote or not, the culture you build is a direct result of the time and effort you put into it. In hindsight, one of the smartest things we’ve done as a company is invest in People Ops.

Building relationships.

In a remote culture, it’s easier to get a productive 4–6 hour block of work done during the day. But one of the tradeoffs you make is that it’s not natural to develop close relationships with your teammates. Aside from work-related discussion, there are no social outings, no casual lunch conversations, usually no friendships that also exist outside of the workplace.


I mentioned earlier that it’s harder to be a manager in a remote culture, and I’ve only realized this in the last year. I’m a huge believer in the Players and Coaches philosophy, which dictates that people be in a dedicated Player (individual contributor) or Coach (manager) role.

FAQs about remote company culture

Q: Where can I read more about building a remote team?



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