For 30 minutes three times a week, the team at 15Five gets together for all-hands meetings. Wednesdays start with a 5-minute meditation. And Fridays are reserved for questions and storytelling—the opportunity to connect as human beings working toward the same goal.
If that seems like a lot of getting together for a software company of 88 employees, that’s because they’re located in 18 different cities around the world in six different time zones.
A distributed team hasn’t deterred the employee performance management company from landing customers—the count is well over 1700—nor investors—they raised an $8 million Series A round last fall.
And it hasn’t impacted the growth of a product team either. VP of Product Holly Kennedy has led from her home in Utrecht, Netherlands—a historic town 30 miles south of Amsterdam—for the last two years. She has a PM in Spain, another in San Diego, and two product designers in San Francisco, and plans to double headcount this quarter.
And though she tried to fill a new PM role in one of the company’s core cities of San Francisco, New York, and Raleigh, the better candidates came when she opened up her search to regions around the globe.
While remote and distributed work is certainly an emerging trend for hyper-growth companies, the nature of product management makes it inherently difficult—collaboration and communication are two of the most critical skills for product leaders. For Kennedy, a deliberate approach to managing her team is especially necessary. Not only is she remote, but she’s leading a product team for the first time.
After a decade as a designer, Kennedy became 15Five’s defacto product manager soon after she started with the company full-time in 2015. They wanted to expand from a simple weekly employee check-in tool sold at a flat fee, to an entire platform for employee performance management and engagement.
Kennedy, the company’s only UX designer, found herself developing features that could be sold at various price levels. The product-focused work was so consuming that she soon hired a UX designer to take over her original job. And when founder and CEO David Hassell stepped away from leading product strategy to focus on building sales and marketing teams to target larger customers, she took responsibility for product. She became head of product and joined the leadership team in May 2018 and was promoted to VP, Product in December.
After two years of full-time travel during her first two years with 15Five, Kennedy and her family made Utrecht home. And since then, she’s developed some best practices for leading a remote product team.
First, she structures her day to maximize the time she spends with the team. She’s typically available for meetings from 12-8 p.m. and asks her team to ensure there are at least four hours of crossover work each day. That means the San Francisco team often starts at 7 a.m.
Kennedy’s entire recruiting process factors the remote nature of work at 15Five. Potential employees need to be comfortable with the challenges they will face working remotely and interacting primarily through text and video. While a lot of candidates are drawn to jobs at 15Five due to the relaxed rules around location, Kennedy says she only considers PMs and designers who have done it before.
“There are challenges of working by yourself,” she says. “It is a risk to take on someone that hasn’t experienced that before and isn’t aware of what it could be like.”
Though Holly says the tech stack for a remote team is “complicated”, it plays a critical role. Her team uses Zoom and Slack for communication, InVision for collaborative design, whiteboarding and prototyping, Jira for managing and tracking projects, Mural for customer research synthesis, NomNom for tracking trends in customer feedback, and Quip as a companywide system of record for documentation and knowledge transfer.
And 15Five, of course. “I don’t know how this would work without it,” Kennedy says. “My team is checking in with me every week, using it to track our goals—both departmentally and for individuals—and to plan our 1:1 time well.”
As a new product leader and remote worker, mentorship and community building have helped Kennedy stay on top of trends in the field and gain access to talent. She’s lent on advice and learnings from the vice president of product at a startup she joined prior to 15Five.
“I learned how to balance the customer need and internal stakeholder need,” she says, ”as well as what is happening in the market and thinking about the why of product strategy.”
She’s also active in the product management community, sitting on ProductCraft’s own Debate Club. In fact, her response to a recent debate question around remote work drew a compelling PM job candidate who recently accepted an offer to join the team. She’s based in Virginia Beach.
Ultimately, remote work is most successful when it’s supported at the leadership level. Hassell leads the company from Sedona and puts processes in place to support his distributed team. Kennedy points to the company’s core value “grant trust and be transparent” as a guide for remote workers, and 15Five’s entire platform—encouraging self-review, relationship-building between managers and employees, transparent feedback and communication, and recognition—both empowers them and enables them to uphold that value.
But inevitably, in-person time matters too. That’s the why behind the frequent weekly digital meetups. The leadership team also meets in person twice a year. The company plans an annual weeklong retreat for the whole team and a separate week brings together product and engineering in some city around the globe. Kennedy calls those times each year “fuel”, and “what makes being remote work.”