How debate over an invoice prompted this AI startup to reimagine its coaching program

Clay, an AI sales and marketing startup, is scaling rapidly. The company’s headcount went from 80 to 600 employees over the last year, according to its head of people, Alex Shapiro. And it recently closed an $115 million funding round, a development that’s likely to add more fuel to Clay’s growth.

Moments like this are a good opportunity to remake the case for certain employee benefits, Shapiro said, and Clay’s longtime coaching program is one offering that recently warranted a second look.

Shapiro recently told us how the benefit is evolving, thanks in part to input from Clay’s head of finance, Karan Parekh.

Coaching at Clay. The startup, which was first founded in 2017, has long offered professional development coaches to any employees interested in these services. Clay built the program in-house, hiring a roster of coaches who could bill the company up to $5,000 a month, or the equivalent of 10 sessions, Shapiro said.

Shapiro said the coaching program is a hallmark of the company’s “individualistic” culture, as leaders seek to support employees on their own personal journeys and career paths. At the time Clay’s founders developed it, they were interested in shepherding employees through “moments of change and growth when we don’t have a structured people team.”

This goal continues to be relevant today, during “a moment of extreme growth” for the company, Parekh said. “We’re asking a lot of our employees, and so there’s an obvious value to being able to give them the scaffolding and resourcing that they need to navigate that change.”

Turn and face the (Clay) changes. As Clay evolves, it stands to reason that its coaching program should evolve. Shapiro recently made the case to expand Clay’s roster of coaches, as well as bring on coaches who are more suited to targeted interventions with specific types of employees.

A more targeted coaching approach might involve bringing on someone to work specifically with first-time managers of managers, for example. “That was a place where I thought, really specifically, we might want to look from an organizational structure standpoint. Somebody who’d never had direct reports before who now was managing several layers,” she said.

The catch? Offering more bespoke coaching services would likely mean making a deeper investment in the coaching program.

An invoice for one of these targeted coaching services prompted Shapiro and Parekh to engage in a debate about whether such coaches were worth the investment.

Keeping track of benefits spending can be particularly challenging for a high-growth company like Clay, where headcount shifts so often, Shapiro said. Moments like this debate prompt her to ask herself, “did I actually just add a bunch of money on top of an already large line item, or did I think full stack about that entire investment in that bucket?”

Beyond input→output. Clay’s people and finance chiefs ultimately came to a consensus by aligning themselves on the goals of the coaching program, Parekh said. They decided to pilot a program offering more targeted coaching interventions, with the goal of offering better support to first-time managers.

It’s unclear which approach will yield better outcomes for the company, but Parekh said he’ll be looking at metrics like performance by teams with managers who are taking advantage of the new coaching offerings.

Given the pace of change at Clay right now, Parekh said he feels comfortable being “a little bit more generous, forward leaning, and experimental in some of these programs.” During his back-and-forth with Shapiro, he said he’d learned that “it’s okay if something doesn’t have a direct input-output,” even if that’s the type of benefit he’s most comfortable with as a finance chief.

Measuring return-on-investment doesn’t have to be all about numbers, he suggested. “We can kind of observe the things qualitatively that suggest that we should try something here and see what happens, and I think that’s okay, too.”