Taylor Roa

From Staffing Desk to Zero to One Builder

Agency work taught Taylor the craft, but it also revealed what he actually wanted. He was helping build teams he would never get to join. When he moved to Boston, Flywire, then a Series C fintech, scooped him up. That became the first talent function he helped build, taking it from roughly one to ten. He has built several more since, most of them from zero to one.

The zero to one work is where his instincts sharpened. Building a talent function before there is a playbook, a brand, or a budget forces a recruiter to think like an operator, and Taylor has now done it enough times to have opinions about what actually matters and what is decoration.

The People Who Shaped the Playbook

Ask Taylor who shaped him and two names come quickly, from opposite ends of the spectrum. The first is Mike Massaro, the CEO of Flywire, a sales leader who was tapped for the top job when the founder stepped away. Taylor calls him one of the best leaders at scale he has ever worked under, particularly on trust and culture building, and on creating a team first environment where everyone runs in the same direction. What stayed with him most was not a business lesson at all. Years after Taylor had left Flywire, going through some difficult personal chapters, Massaro reached out personally. "I don't know how he has such a high capacity for building so many deep relationships," Taylor says. Flywire also gave him one of his most durable operating principles: hire for teams, not always for individuals. Compile complementary strengths across a group rather than hunting for every strength inside a single person.

The second is Jane Jackson, VP of People at Wistia when Taylor was hired to head up the talent function there. Wistia was a tenth the size of its biggest competitor, Vimeo, and went toe to toe with it anyway, winning clients and, in Taylor's view, shipping a better product. In a single year the company went from a point solution to a platform, building four features zero to one. It was also, he says, the most people first company he has ever been part of, a business punching far above its weight on revenue, team size and competitive set while insisting on putting people first. Jackson was central to that. "She's able to really keep the business first without sacrificing the human element," Taylor says, describing her as a thoughtful people leader who works hard and never lets the two priorities cancel each other out.

The Contrarian Read on AI

Ask most talent leaders what has changed in the last year and they reach for the technology. Taylor goes somewhere else first. "The biggest thing is market conditions and how quickly they change," he says. He spent three years, from 2020 through 2023 and 2024, talking about phases of the pandemic, and he sees a pendulum of market competitiveness swinging back and forth, and swinging faster each time. That pendulum, more than any tool, reshapes what a talent job actually is.

On the technology itself he is measured rather than breathless. Large language models, in his experience, are a deeply personal productivity gain: you learn to use them in your own way and fill your own gaps. Scaling that across a team is the hard part. Shared GPTs still run into individual memories and outputs that drift over time, which means getting a whole team to use one consistently is genuinely difficult and can end up hurting efficiency at scale. Where the gains are real, he is specific. Dumping ATS data into Claude or ChatGPT to draw meaningful insight is dramatically easier than it used to be. Drafting documents is faster, though as he puts it, faster is not necessarily better.

His read on today's market is unsentimental. It is hyper competitive for roughly the top one percent of specific skill sets, while for huge swaths of the market it is simply hard to get an interview. Inside the fast scaling tech companies that are winning, he argues, the recruiter's role has become more human, not less. A senior talent partner today is a combination of an HRBP and an account executive: strategic enough to advise a hiring manager through high ambiguity as team structures take dramatically different shape, and commercial enough to go win the people nobody else can reach. "Nobody's going to respond to your cold outreach anymore," he says. The ones who do respond are often not the best players, because the best are inundated. Which is why he believes everyone has to be an executive recruiter now: map the market, identify the white whale prospects the way an enterprise AE would, and build a strategy to break into those accounts through network recruiting, relationship building and warm introductions.

Drop the Ego, Join the Best Company

Taylor's advice splits by seniority. For senior leaders navigating what he calls a brave new world, where the rules change quickly and the structures of the fastest growing companies look nothing like they used to, his counsel is blunt: drop the ego and join the best company. It is a lesson he learned later in his own career. Choosing for the role and the title tends to land you at less exciting companies than you would otherwise pick. He would rather be part of the next future household name and stay genuinely open about where he fits on the team, knowing that answer changes fast when a company 10Xes in size. He notes that at many of the best companies there are six or seven heads of talent operating as individual contributors, people who would carry a VP title anywhere else.

For newer talent professionals his message is that the job is a lot harder than it looks. To do it well at a startup today, he argues, you need an operational skill set, almost a consulting toolkit: build the right relationships, hold the right contacts, ask the right questions. "If you are in a recruiting role and you don't understand your business, you cannot succeed," he says. His prescription is to be relentlessly curious and to treat the job as an apprenticeship. Pretend you want to be a founder someday and this is your crash course. Bring that entrepreneurial mindset to how you grow, because in his view the age of the recruiter as facilitator is over. Reviewing resumes and marking the next step in the process is no longer valuable work. That can be automated. Everything upstream of it, the judgment, the market intelligence, the relationships, cannot.