Hiring, Compensation, Benefits in a Remote Team

Remote work is not for everyone.

Some people don’t enjoy not being in the same physical location as their coworkers. And some people, quite frankly, aren’t very good at it. Because of this, a big part of working well in a remote team well is making sure you are choosing people for whom remote work will work well for, in the first place.

This includes figuring out, yes, first who exactly to hire and what to hire for. But it also includes executing well on how you hire, how you choose to compensate those folks fairly, and how you think about providing benefits in a remote team.

Based on numerous remote companies who’ve hired folks successfully (and unsuccessfully) over the years, data from our remote work survey, and insights from 1,000+ managers in our online leadership community in Know Your Team, The Watercooler, here are the most important factors to consider as a remote manager when hiring for your team:

What to hire for in a remote employee

Empathy – You get a Slack message from someone making a request of you. Their tone is curt. You feel a bit put-off. Are they mad at you? Should you say something? This situation happens a million times, over and over again. When you’re working remotely, there are going to be a myriad of moments where you have to either read between the lines or take things with a grain of salt. This is where empathy comes in. You want to hire folks who are aren’t going to assume the worst, overreact, or take things personally in communications. They take things in stride, and have empathy for the team in terms of why someone might be communicating in a certain way. Wade of Zapier describes this necessary empathy well:

“We like folks who have a lot of empathy and are really good, just helpful people because you’re working in Slack and in text all day. You need to be able to empathize when maybe a sentence doesn’t come off quite right, or whatever, you’d be like, oh, I trust that they had good intentions here, this wasn’t meant to be, you know, harsh to me or whatever right. Those are important values that we have that lend themselves well to remote environments.” 

Manager of one – In the book, Rework, the Basecamp founders Jason Fried and David Heinemeier Hansson, they discuss how the ideal employee is one who manages themselves. This could not be more true of remote employees in particular. In their guide to remote work, Zapier talks about how the “propensity toward action” and ability to prioritize are key traits to look for in a remote employee. Help Scout similarly extols how “self-starters” tend to make the best remote employees. And Doist has written how “when everyone on the team is remote, it’s vital to hire proactive, curious people who won’t wait for a specific set of instructions.”

Excellent writing skills – As we’ve discussed, writing well is essential to being a good remote manager. But it’s also paramount for remote employees too. With most of communication happening in a remote team that’s written – be it Slack messages, emails, etc. – “if someone struggles to write clearly and concisely, they’ll struggle in a remote team,” as stated by Zapier, a remote company with 200+ people. Doist in fact emphasizes a written cover letter as one way to filter and zoom in for people with excellent writing skills.

Prior experience in a remote team is preferred – One observation that many experienced remote managers will share is how they historically have had difficulty hiring more junior people in a remote team. This is because junior people tend to require greater mentorship — mentorship that is more easily accessible when in person. They also don’t have a lot of experience, if at all, with remote work and tend not to be as proficient of writers or modes or reading emotional tone. Now this isn’t to say you should never higher more junior folks. It’s just to bear to mind that onboarding and strong training should be emphasized and likely more focus will need to be applied, versus than when hiring junior co-located employees.

How to for hire remote employees

Zoom in on real work.

There’s nothing like knowing if someone can work well remotely as looking at someone’s work, itself. Many remote companies will do this, whether it’s an “audition” like at Auttomatic, or paying candidates for one or two weeks of a consulting project as they do at Basecamp. At Know Your Team, when we hired Mandy, we worked with her part-time, remotely, and compensated her as such at an hourly rate as a consultant for about two months before we decided to work full-time with her. When you zoom in on the real work instead of the resume, you focus on what matters: The work itself.

Assume more time.

I recently interviewed Nick Francis, CEO and co-founder of Help Scout, about how he thinks about hiring at his remote company and he admitted a very interesting insight to me: He’d noticed how when you’re hiring in-person, it’s all about moving quickly. You hear from someone via email, they’ll get interviewed over the course of the next few days, and oftentimes, an offer is either made on the spot or at the end of the week. In a remote setting, that timeline is extended. You may actually spend weeks sourcing candidates, and then months interviewing them and doing a trial period with them. It’s different. For example, here are the hiring processes and timelines share by Buffer, Doist, Gitlab, Zapier, and Automattic.

Examine the writing.

With writing being so important to working well remotely as we discussed in Chapter 2, it’s no wonder that hiring folks who are strong writers are key. It’ll show immediately, as you begin to work with the person. The numerous chat messages, write-ups, and emails will accrue – and you’ll want those communications to be as clear and crisp as possible. Basecamp strongly discusses how when two candidates are equally qualified, they always hire the better writer.

Where do you advertise roles and source candidates specifically for remote candidates? Based on input from 1,000+ members in our Watercooler community, many managers’ found remote job boards to be useful – particularly We Work Remotely. (FlexJobs, and Remote.co were also mentioned). Additionally, as with co-located managers, remote managers also highly relied on their own network and promotion on their company’s blog and social media. Interestingly, another means that came up was promoting the job description to your own customers. Noted one Watercooler member: “Having over 10,000 paying customers, we will just send an email out to our customer list with the new position. Just recently, we had over 50 people apply for a part-time, remote position. This serves two benefits. (1) It shows our current customers that we work hard to find people like them who know the product (2) It helps us find high-quality candidates who identify with our company’s brand and values since they were a customer first.”

How to compensate your team when you’re in different locations

Fairness of compensation in different locations, with different costs of living, is something that frequently comes up for managers of remote teams. Most commonly there are two approaches to thinking about fair compensation for remote employees:

Location agnostic - Some companies pick one location as a base for setting a standard for what salaries should be. For example, Basecamp uses San Francisco as their base city. They look at comparative data sourced by Radford, a pay research company, and then target 95th percentile for the role and seniority. They discuss more about this practice here. According to Basecamp CTO David Heinemeier Hannson, they “never felt good about paying someone less because they choose to live somewhere cheaper. That should be their gain [as] remote employees.”

Location sensitive - Other companies do factor in location as part of the compensation strategy for remote employees. For them, it feels arbitrary to pick a specific city for the base rate, as a remote company. They also often factor in other lifestyle factors and years of experience as well, into the pay scale. Buffer famously has an open, transparent salary calculator, which you can read about here.

Favorite benefits and perks for remote employees – especially in different countries

When you’re co-located in an office, it can be easier to offer team benefits and perks: Team lunches, happy hours, gym memberships etc. In a remote team, it’s a bit trickier. You want to figure out, how can office perks can be enjoyed by everyone? Or does there need to be entirely different perks for remote employees all together?

Here’s what Watercooler members mentioned as things they offered in their own remote teams:

  • “Happy breakfasts” - Randomly pair remote staff who have non-work Skype call over coffee.
  • Virtual happy hour every week - Use multi-way video conference and have a virtual happy hour every Friday early evening, with everyone’s favorite drink, whether it’s tea or a martini.
  • Schedule remote employees to drive / fly in for the weeks when you have some sort of big party or event (but don’t make it expected, so the pressure isn’t felt to travel if folks don’t want to). Potentially even include and invite their families.
  • Consider offering food delivery for remote workers on days you’re providing catering in the office - For example, one Watercooler member held a company-wide pizza party, where she coordinated surprise pizza deliveries for everybody, and then hopped onto group video chats to show off pizzas and enjoy a big goofy synchronous lunch break. Another Watercooler member has a tradition of ordering sweets for people’s birthdays, and for the remote person’s birthday he had doughnuts delivered.
  • Offer “equivalent” benefits - If you negotiate a gym membership near the office for employees at HQ, also offer a comparable gym membership to the remote employee.
  • Make sure to buy hardware (computer, monitors, etc) for remote employees. While it may seem tempting to ask a remote employee to use their own equipment, there was strong consensus from remote managers in The Watercooler that you invest in getting hardware for your remote team members to use. Wrote one Watercooler member:

“Hiring and onboarding new team members is a big investment that we take very seriously – and the last thing we want to get in the way of success are small things like equipment. If you already purchase machines for your non-remote team members, then I especially recommend you do the same for your remote team members […] Remote employees can sometimes feel like second-class citizens if they see that they receive different treatment from co-located employees, and this can have a negative impact on culture.”

While not wholly different from hiring in-person, hiring remotely is different. I’m hoping these references and words of advice can serve as a starting point as you decide for your team who and what makes the best fit, given the environment you want to create.


  • Hire for empathy, the ability to manage themselves, excellent writing skills, and (preferably) prior experience in a remote team.
  • During the hiring process, zoom in on real work, assume it’ll take more time than you think, and examine people’s writing skills.
  • To promote the job, consider advertising on remote job boards, asking folks in your network, and also advertising the job to current customers.
  • Ensure fair compensation for your team – this can be either location agnostic or location sensitive.
  • Consider having perks and benefits that “mirror” what you’d have for your co-located, in-office employees.

Put this into practice with Know Your Team:

  • Once you’ve hired your new employee, use our Icebreaker feature to kickstart your onboarding process – it asks five fun questions every time you add someone new to Know Your Team.