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Working from home for the long haul with Jonathan Rayback

Pluralsight - Jonathan Rayback, illustrated by Matt Peet

Illustrated by Matt Peet

A year ago, if you had asked several tech leaders if they would consider letting their entire team work from home indefinitely, then asked the same question to the same leaders after COVID-19, chances are their responses would have shifted toward the “yes” column. Since the global work-from-home experiment began in response to the pandemic, a Gartner survey revealed that about 74% of CFOs are planning to shift at least some of their workforce to a permanent WFH status.

With nearly two decades leading software engineers, including 12 years in leadership at Motorola, Jonathan Rayback, VP of engineering at Evernym, had always believed that distributed teams created too much distance between developers. 

“Alistair Cockburn, the famous agilist used to say, ‘The optimal physical distance between engineers was the length of the school bus,’” says Jonathan. “If it was any longer than that, they wouldn't even get up to go talk to each other, so even having engineers on different floors was considered to be bad practice.” 

In 2019, Evernym, a self-sovereign identity company, had development teams based in Utah and Belgrade, Serbia, and they had plans to expand by acquiring more space in both locations. But being a startup and feeling the work-life landscape and global economy shifting beneath their feet, Jonathan made the case for doing the opposite.

“I just said, ‘Listen, this is ridiculous. We shouldn't be paying rent for a space that we're not using.’” Jonathan recalls. “So we looked at it and decided to take the plunge. Yesterday we couldn't spell work from home. Today we all are.”

We sat down with Jonathan (over Zoom of course) to see how this decision came about and how he and his team managed to not just survive the shift to WFH, but grow faster than before. He outlines three takeaways for those looking to distribute their team permanently.

Build stability through flexibility

Major decisions like shedding all physical locations shouldn’t be taken lightly. It’s important to look at how moving home will impact team dynamics, so your engineers feel like they have the support system they need to do their best work. Jonathan has found a few areas that adding a little flexibility can go a long way.

Revisit the org chart

When everyone is working in the office, it’s easier for leaders to check in with individual engineers, see who’s working on what project and have on-the-fly meetings when the situation calls for it. Going online strains many of the opportunities leaders have taken for granted. Jonathan quickly realized that his organizational structure needed refinements to better serve his team.

“Even though we're technically a flat organization, I've had to develop some people into more leadership roles, because I just can't be aware of everything that's happening all the time,” he says. “So, I've asked a lot of our senior developers to take on a sort of quasi engineering management role without anyone reporting to them. It allows them to get involved in a little project management and decision-making while being the senior person in the room.” 

By being flexible and creative about the structure of his team, Jonathan has made room for senior engineers who want to explore leadership responsibilities. But the forced change of a fully distributed team also opens up an entirely new pool of talent when recruiting. 

“In the past, I've only wanted people in one of our cities. Now we have a lot of flexibility to hire anywhere,” Jonathan says.

Normalize digital collaboration

Communication is key to any successful engineering team, and while in-person is still the best way to forge strong relationships, the pandemic has altered that dynamic for the foreseeable future. Jonathan had long felt there was no substitute for being in the same room, but over the past few years digital, real-time communication became more realistic. When COVID created an immediate need, and he watched collaboration continue, his views shifted. 

“Technology has gotten better and we have things like video conferencing, Slack and a new generation of developers who have come up more comfortable in those types of media. So my attitude has really modulated and come around 180 degrees, Jonathan says. “Yesterday, we couldn't spell work from home. Today, we are living it and we had to commit to making it happen and just learn as we went."

Because Evernym is global, time zones and team schedules are something that Jonathan and his team have been navigating on the fly.

“For our offshore people, it's required more flexibility. They tend to start their days later now and work a little bit later. I think they are naturally finding it more convenient to be aligned with other members of the team,” Jonathan says.

Foster trust by being human

Leaders have a responsibility to be an example and a defender to those on their team. Through uncertainty the importance of setting the right examples is amplified. Since the pandemic, Jonathan has refocused his efforts on making himself an ally to his team members.

Create meaningful meetings

Meetings are one of the most significant changes with a distributed team. During a time of constant global upheaval, Evernym found that holding regular digital meetings served as a stabilizing force while keeping teams aligned.

“I have a weekly huddle with the whole engineering team, and after we went fully remote we decided to do an all-hands every Friday morning, where the whole company gets together to just chat.” Jonathan says. 

For individual engineers on his team, Jonathanadopted an ad-hoc approach to 1:1 meetings. Rather than creating an agenda with a checklist of topics to cover, he worked to simply make himself available to each individual engineer. 

“I'll catch up on how they're doing, how their family is doing and how their job is going. You know: ‘are they enjoying the work they're doing? What kind of impediments can I remove from their path?’” Jonathan says. “Sometimes we talk about family problems they're having or health problems they're having, that have nothing to do with work. I have found that when those things come up, just listening and being supportive having some compassion and expressing that is critical.”

Take personal time seriously

An engineering leader who is always “online” according to Slack could be inadvertently sending the wrong signals to the team. This is especially true when everyone is working from home and could theoretically be online any time they’re needed. Jonathan understands he works with humans with real human needs, and responds in kind by showing them he is in fact, human.

“I've always had this policy about PTO where I want my team members to let me know when they’re taking time off, but I don’t think I’ve ever said no to someone requesting time off,” Jonathan says. “Once that habit starts getting set, they feel like I'm going to reject their request and will just stop asking.” 

To ensure his engineers feel the freedom to take time off when they need it, rather than when it’s convenient for the business, Jonathan sets the tone by doing it himself.

“It's important for us to lead by example and to take time off. And when we take time off to communicate clearly that we trust the team,” Jonathan explains. “I took time off recently while we were in the middle of some pretty big customer projects. There were a lot of things in flight, and it would have been really easy for me just to try and stay in touch, but I just turned everything off and I was totally out.”

Move fast by staying focused

When it comes to a major workplace shift, every business leader should be looking at the impact it will have on the organization’s goals and desired outcomes. While many businesses are struggling to keep their company above water, Evernym’s challenge has been to keep up with the demand. Jonathan is willing to make big moves to meet their targets, but always has a few things to check before he asks his team to make a leap.

Aim small and stay lean

Leaders can’t and shouldn’t try to be buried in the nuts and bolts of all the lines of code submitted by the developers. Likewise, they should avoid letting their team go too long without some form of check-in. Jonathan believes in tackling projects in small bites, more often, to keep the team engaged while also surfacing issues earlier.

“I want tasks to be a day of work, so we're operating on small increments--small chunks of value add,” he says.

Beyond submitting code in small increments, Jonathan’s team is multi-faceted and gritty. Not to mention intimately aware of the needs of their customers. 

“We ask a lot of our development team,” he says. “Engineers rotate through being the role of primary customer support every week. When your job description is to do a bit of everything and you’re looking out for the customer to really put them first, people start to buy into it.”

Be clear and deliberate

It can be challenging to press others and yourself to stay on target. Jonathan believes that when everyone is wireless, the need for clear objectives and continuous alignment requires leaders to be more deliberate and focused in their dialogue. 

“I'm always pulling people back to the objectives. It's this constant reminder of, ‘If you're not working on something that's directly related to these nine objectives, you should be raising your hand,’” Jonathan says. “We should be really intentional about what we said we needed to get done. And that requires a little bit more rigor in a remote environment”

Jonathan highlights this simple focus on “the why” that allows his team to make decisions easier, remove roadblocks faster and ultimately deliver better products on time.

“Teams feeling like they've got adequate context to make the decisions that they need to make, without having to constantly look over their shoulder and wonder if they're doing the right thing, is really critical,” he says.

Stay patient and persistent

Patience is hard. It’s easy to get ahead of yourself with the scope of a project or try to push change too fast, but Jonathan believes development is an endurance race, and it’s better to pace yourself.

“I've learned that patience is probably the most important thing and is what allows an organization to make the little incremental steps of progress,” he says. “Maybe you just get one step forward and then because of whatever business circumstances or you need to refocus somewhere else, you don't really get to make any more progress on that item. Just don't lose that step, and you can come back to it.”


Don't be afraid to be bold, don't be afraid to take action and err on the side of taking action,” Jonathan says. “Learn from empirical data rather than just hypothesizing. Never be afraid to learn from experience. You can't always think it all the way through to the end, you know, just go for it.”

This mentality is how Jonathan and his team moved from no plans for a distributed workforce to growing a business with everyone working from home.

  • Build stability through flexibility: Creating a consistent environment for your team is critical when no one is in the office. Things like revisiting the org chart to address WFH changes, and normalizing digital communication and collaboration can help foster the stability needed.

  • Foster trust by being human: It’s important to keep your team’s health in mind, even when everyone is working from home. This means creating meaningful meetings and taking personal time for you and your team seriously.

  • Move fast by staying focused: Making big changes can be difficult on engineering teams. It’s important to aim small and stay lean, be clear and deliberate in communication while keeping you and the team patient and persistent.