People operations has spent decades fighting for legitimacy, but Natalie Ledbetter is showing that the next chapter won’t be won through frameworks or slogans. Natalie is the Managing Partner of Ledbetter Global Advisory and a former operating partner and Chief People Officer at Boldstart Ventures. She works with Series A and B startups, where I’ve spent a bunch of time, so we bonded over how the decisions we make impact runway and revenue in ways big tech recruiting just doesn’t.
Her career spans startup operating roles, VC work, and fractional CPO leadership, a combination that gives her a rare vantage point on how companies actually scale, break, and rebuild. And what she sees is clear: people teams only earn real influence when they operate like business operators, not administrators. I agree.
In this episode, Natalie and I dig into what that really looks like. We talk about why most HR teams are still positioned as tactical support functions, and why the only path out of that is developing fluency in the business itself, understanding revenue mechanics, customer segments, deal cycles, employee lifetime value.
Natalie walks through how she rebuilt talent systems from the ground up at Stash, starting with a hard look at their customer base and the uncomfortable realization that the employee population didn’t reflect it at all. Instead of spinning a narrative, they said it publicly, owned the gap, then rebuilt everything: interview loops, candidate profiles, employer brand, compensation leveling, behavioral norms, and even how the physical office was designed to create engineered alignment across teams. The outcome wasn’t just a better hiring system. It was an organization built intentionally, with people operations acting as the connective tissue between culture, product, and revenue. I appreciate how Natalie opened up to this experience. It’s not always pretty building a People and Talent function. Props for sharing this story.
A big through line in this conversation is identity, both personal and organizational. Natalie talks about joining companies as an early employee and stepping into environments where the culture hadn’t yet been formed. In those moments, founders shape the majority of what the company becomes, whether they intend to or not.
We also talk about the lived experience of recruiting inside startups, the part most people gloss over. Recruiting isn’t glamorous. It’s accountability, constant pressure, and a front-row seat to every downstream problem. Natalie makes the case that TA is both the first line of defense and the architect of the organization. You’re not just filling roles. You’re shaping who the company becomes a year from now. And that’s why motivation matters more than pedigree, especially in an industry where burnout is real and early-stage work demands more than most people realize.
The 996 debate? Natalie laughs a little because it’s been happening for years we just finally named it.
A thread I kept coming back to is the skill set startups actually need. Not generalists in the traditional sense, but people who operate like Swiss Army Knives, curious, adaptable, and willing to drop into ambiguity without flinching. Natalie argues that curiosity is the defining attribute of great startup operators. Not the title. Not the pedigree. The willingness to get close enough to the work to understand it end-to-end, whether that’s building systems, mapping employee journeys, or re-architecting a talent machine that touches every point from sourcing to alumni.
We eventually zoom out to the market itself. Fewer jobs. More uncertainty. And a hiring landscape where, as Natalie says, referrals all day. People aren’t getting roles through cold applications alone. They’re getting hired because someone knows them, trusts them, or has seen their work. That’s why relationship-building has become the core skill TA teams can’t outsource, the one area AI hasn’t solved. And it’s pushing recruiters to rethink their own craft: build your network, understand your systems, and find one friction point each week you can remove through better design or smarter tools.
This conversation mattered to me because it validated so much of what I’ve been seeing building this show and running my own recruiting practice. Recruiting is not glamorous work. People ops is not glamorous work. It’s operating with curiosity while working close enough to founders to feel the discomfort of growth. And it’s having the confidence to operate with conviction to TCB as a builder. Natalie brings a level of honesty to this craft that’s rare, especially in a moment where people teams are trying to redefine themselves without losing their grounding. She champions operators who are willing to build, the ones who don’t wait for permission to sit at the table because they know the business well enough to walk in on their own.
Tl;dr - the future of people leadership will belong to those close enough to the work to understand the business, and bold enough to build systems that actually scale with it.
Episode 013 of Building the Talent Machine is out now 🔊
🎧 Listen on Spotify
▶️ Watch on YouTube
Follow Natalie here: https://www.linkedin.com/in/natalieledbetter
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