John Ryan

Recruiting Boot Camp, Billed by the Hour

An uncle who owned a staffing agency gave Ryan a rough sketch of the industry before that first internship, enough to know the work existed and roughly what it paid. The real education came later. Three months into the full-time role that followed graduation, a LinkedIn message arrived from a recruiter at TalentFusion, an RPO that had been acquired by the job board Monster.com. Ryan still returns to how much turned on that one piece of outreach.

The TalentFusion model was unusual and, in hindsight, ideal. Recruiters were hired out by the hour, which meant Ryan split a 40-hour week across a roster of clients: five hours here, 20 hours there, each with its own hiring bar and vocabulary. The roles ranged from truck drivers and plumbers to software engineers, enterprise solutions architects, and a head of sales. Ryan describes it as recruiting boot camp, a compressed tour through dozens of position types, company stages, and industries that would have taken years to accumulate in a single in-house seat.

Five Hundred to Three Thousand

When a manager at TalentFusion left to become head of talent at Toast, Ryan came along. Toast sat at roughly 500 employees and was approaching its Series D. In just under three years, the company grew to 3,000 people and became a unicorn.

Then COVID arrived. Toast had not yet pivoted into new product lines, restaurants shut down, and roughly 70 percent of the staff was laid off. Ryan is careful to finish the story properly: the company rebounded, went public, and built a strong business. But the moment redirected a career. Ryan joined Talentful, another RPO, and stayed four and a half years, starting as an embedded talent manager and rising to talent director over a portfolio of technology companies from Series A through publicly traded. The team reached about 55 people by the time Ryan left, from coordinators up through TA managers and TA operations managers. In January 2025 came the move to EvenUp and the return in-house, now a little over a year and a half in, a shift Ryan clearly welcomes.

The Hire Who Became the Boss

The mentor Ryan names first is someone Ryan recruited. At Toast, Ryan served as the recruiter on the company's first talent operations hire, a head of TA ops brought in when the company was close to 1,000 employees. Ryan notes how much the discipline has moved since: today Series A companies bring in operations talent early.

That leader then turned around and hired Ryan as the first individual contributor on her team, the pivot out of IC recruiting and into operations. What made the difference was not instruction but latitude. She was hands-on where it counted and otherwise gave Ryan room to try things and to fail at them: building dashboards in a BI tool, standing up enablement for the team, owning systems end to end, running vendor discovery and negotiations. None of it was familiar. All of it stuck. Years later, that door remains open, and Ryan counts the wider network of managers, peers, and direct reports as a genuine competitive advantage.

Build Versus Buy

Ryan's read on AI is measured. So far it has not taken jobs in talent; it has supplemented the teams already in place. That could shift, but recruiting, Ryan argues, is uniquely human compared with most corporate functions. As a candidate, Ryan would far rather work with a seasoned recruiter than an automated one, while allowing that a younger generation may feel differently. The human element, Ryan expects, is not going away.

What AI does reliably is absorb the repeatable work. Anything with logic to it can be automated: interview plans, scoring rubrics, intake meeting notes, job descriptions, the administrative layer that was never the stimulating part of the job. The more interesting consequence is strategic. Teams can now assess vendors through a build-versus-buy lens instead of defaulting to purchase. A recruiter on Ryan's team built a total compensation view using Claude: plug in a candidate's salary, equity, bonus, and currency, and the dashboard models what that equity is worth today and what it could be worth at different future valuation stages, wrapped in a narrative of where the company has been and where it is going. Ryan points out that companies sell that exact product. Five years ago, the team would probably have bought it.

Most organizations, Ryan believes, are still using AI at an elementary level. The excitement lives further out: getting multiple systems to talk to each other, and building bespoke tooling shaped to one specific team at one specific company.

Advice for Talent Leaders

Ryan frames the next priority less as advice than as an open problem currently being worked. The recruiting side of the house at EvenUp now runs on predictable data. The team can say with reasonable confidence when a role will close, and there is a shared definition of what good looks like.

The gap is everything after the offer. Ryan wants to connect the full employee life cycle, from the moment a person enters the recruiting funnel to how they perform, get promoted, or eventually leave the company. Recruiting metrics presented in isolation invite a fair question: what does this actually mean, and how are the hires everyone worked so hard to land performing? Answering it means baking financial and business impact into every conversation and giving business leaders visibility across the whole arc rather than one slice of it. Ryan calls it P0 heading into Q4 in 2027.