Prickly on Purpose: Hiring Is a Timing Problem

In this episode of Prickly on Purpose, Cactus co-founder and CEO AJ talks with Wendy Moore, founder and CEO of Elevé Talent, about what actually breaks hiring at startups, and why almost none of it is about finding good people.

Wendy Moore is the co-founder and CEO of Elevé Talent, a TEDx speaker, a 20 Under 40 honoree, and the builder of a bootstrapped, referral-only recruiting firm out of Missouri, far outside the usual startup hubs.

Hiring is a timing problem, not a talent problem

Wendy's founding belief is simple and a little uncomfortable: "You can have the best idea in the world, but if you don't have the right people at the right time, it does not matter." Most founders obsess over who to hire. Wendy spends just as much energy on when. Hire the best salesperson in the world before you're ready for them, and they fail, not because they're bad, but because the seat isn't ready for them yet.

Why she won't touch the traditional recruiting model

AJ brings up something founders rarely say out loud: contingent recruiting fees quietly reward the wrong outcomes. Higher salaries mean bigger fees. Turnover means another placement. "The motivations felt misaligned to me," Wendy says. "I also never liked to have any foot in the camp when the offer is being negotiated. I want that offer to be for the best of the company and the candidate, not for me."

Her model is scope-of-work, not contingent or hourly: closer to how a law firm operates than how a staffing agency does. Her team is expected to be strategic and do the unglamorous execution work most recruiters skip. And the actual measure of success isn't the placement, it's getting replaced. "Success looks like we replace ourselves," she says. She's currently helping two long-term clients hire an internal head of talent so she can hand off the relationship entirely. "I'm gonna pass the baton and wish them well."

The two hires everyone gets backwards

Asked where timing goes wrong most, Wendy doesn't hesitate: sales, too early, and ops, too late.

Founders hire a salesperson before founder-led sales is repeatable, "if that motion is not perfected... you're too early to hire a salesperson," or they overhire, bringing in a CRO-level person to do SDR work. On the other end, she sees the chief of staff role show up roughly six months later than it should have. Not an executive assistant, not an office manager: a strategic partner who takes the minutiae off a founder's plate so they can stop working in the business and start working on it. "Once that person's in place, you're like, that's what I can accomplish when I'm not managing this, this, this, and this."

Build a team that looks like who you serve

Wendy's TEDx talk centers on representation, and the logic she gives AJ is practical, not abstract: your team should reflect the people you're building for. A company serving the trades needs voices at the table who understand that world. "Where I see teams stagnate is where everybody's the same... you're just gonna be in an echo chamber at that point." She extends the same logic to geography, operating from Missouri rather than a coastal hub cost her some clients early on, but she's since proven it's an asset: sitting in the middle of the country, she serves both coasts without asking anyone to take a 6am call, and most of her team was hired and onboarded entirely virtually.

What she'd tell any founder about to make their next five hires

Wendy's advice isn't a hiring checklist. It's a sequencing discipline. Plan your next five hires as a batch, and know what each one is meant to unlock before you write the job description. "Too often we get distracted by making a JD... that's not the first step. The first step is thinking through your own strategy." And skip the headcount vanity metric entirely. As she puts it, "this isn't about hitting specific headcount numbers anymore. You have to run so lean for longer than ever before." The mistake on the other side isn't hiring too cautiously; it's throwing people at a problem with no plan for what happens once they actually start.

She's equally direct about AI: it's freed her team from repetitive, tedious work so people can spend more time on judgment and relationships, not less. As she puts it, "AI has enabled us to keep more human in the loop than less." The tradeoff is noise: more volume, more fraud, more tooling required just to manage the flood. Her ambition is to build an AI-native recruiting team for AI-native companies, at a scale where she never has to keep a client on a waitlist again.

Watch the full conversation for more on Wendy's take on chief-of-staff timing, diverse team-building in practice, and what she calls the "revolution" recruiting still needs.