Our startup’s first hire was a fractional Head of Remote

The very first hire at our SaaS startup was (surprise!) not an engineer.

It might seem counterintuitive, but the first person on board at Wingback was a Fractional Head of Remote — and it was the best decision we made.

My co-founder, Torben Friehe, and I knew we wanted to be an asynchronous, fully remote company, and we intended to grow fast. Sure, our first hire could have been a backend engineer or a sales guru. But we’d never attempted to lead a remote team before — our first startup together was entirely in-person. What if we mismanaged our first employees simply because we had no idea how to run a virtual company?

Saying, ‘Please confirm by end of day’ means nothing when everyone’s work days span different hours.

If you have experience leading remote teams, having someone dedicated to remote work processes might not be necessary, but for anyone else, it’s hard to overstate how critical this role is in helping ensure your employees are rowing in the same direction: It’s particularly true for founders and startup CEOs, whose time and mental energy is stretched thin as it is (not to mention our communication skills can be, well, lacking).

As an early-stage founder, your most important task is focusing on your product and making sure you hire the right people, not spending your time making sure each team member has gotten their vacation time approved or has read the company policies.

Our fractional head of remote was tasked with making sure all of our employees, distributed across five continents and nine time zones, have everything they need to succeed and thrive in a company where Slack and Confluence are their office spaces.

This meant investing a lot of time on shaping a fully digital and remote company culture from day zero, including crafting a thorough framework for communications among employees, and building holistic policies that would work universally. Ideally, a Head of Remote is working with the founders on implementing these processes, and listens to the employees and provides feedback to management at the same time.

It’s worth mentioning that the role, as we crafted it, was not meant to be the same as the other “HR” — Human Resources. There is some overlap, but the roles are quite different. A head of remote is not just a glorified HR manager. They make sure that the right processes are set up and that the right tools are selected and used to make remote work successful.

While a typical HR or people ops executive may find themselves dabbling in best practices for remote work, most don’t specialize in it. The dynamics are completely different from in-person, and even hybrid, work. What works well for a traditional office setup simply doesn’t apply when half your team is asleep at any given time.

Take timing expectations, for example: Saying, “Please confirm by end of day” means nothing when everyone’s work days span different hours. So we implemented a 24-hour response time policy, which gives every employee some buffer to respond in a reasonably timely manner while taking into account that everyone is in a different time zone.

Another example involves communication. A company all-hands is great for in-office teams, and we’ve even seen other remote startups adapt the regular company-wide meeting as a way to try to get everyone “synced up.” But we’d argue this is selling a lot of employees short and doesn’t suffice for holistic communication. Why? Because not everyone consumes information in the same way. Some people do great with in-person meetings, but struggle on Zoom calls where they don’t feel engaged and get distracted with notifications. Some people love jamming on a white board with their coworkers, while others really need to be left on “Do not disturb.”

This is only exacerbated with more frequent (and often critical) exercises in communication. We discovered early on that some of our employees could read a Slack message and digest all the information right away, the first time. Others needed to have the information and situation talked through verbally.

So we created a policy where updates are distributed and disseminated in multiple ways, including in text and by recorded video. So whatever traditional HR practices have worked for you in the past may not be applicable, and a Head of Remote can help you identify what’s going to work for your current and future setup.

For growth stage companies who are ready to hire, or already have hired, a full-time in-house HR, an ideal head of remote would be someone who has done this full-time for a remote company in the past. Look specifically at candidates who have managed HR for a remote-only team, not just a company that was temporarily remote during the pandemic and evolved into a hybrid model. Not surprisingly, these people are like unicorns (pun intended), so if you’re struggling to find them, there’s no shame in hiring a freelancer like we did.

Given our stage, we went straight for a fractional hire, and we wouldn’t have done it any other way. Specialized freelancers, because they can work with several companies at the same time, bring an additional layer of insight as to what works and what doesn’t, and for which companies. They offer a unique, unbiased external viewpoint of the landscape, norms and best practices not just in previous years, but right now. These days, that is invaluable context.