Ep 322 – Jessica Zwaan (VP People Strategy and Operations, Leapsome)

1. Forget the traditional 30-60-90. Give yourself a 12-week outcome.

When Jessica joined Leapsome, she didn’t spend her first few months simply observing and waiting to form an opinion. She came in with a clear view of the value she wanted to create — across People Ops, product strategy, marketing, and advocacy — and set herself a tangible outcome to deliver within 12 weeks.

That outcome became an internal “How We HR” document: a point of view on how Leapsome should run People Ops that could also influence product positioning and external content.

The lesson for any leader starting a new role: don’t measure onboarding by how many meetings you’ve completed. Measure it by whether you’ve created something that demonstrates your understanding of the business and gives people something concrete to react to.

“Basically, I set myself a kind of sprint — this is something I want to deliver at the 12 weeks that has demonstrated that I’ve made groundwork on all three of those things.”

Jessica’s take is that the old model of spending 60 days talking to everyone before finally deciding what to do is increasingly incompatible with the speed companies expect today.

2. Run People Ops like a product team: problem → data → impact → roadmap

One of Jessica’s first moves after joining was to bring the People team into the same operating rhythm you’d expect from a strong product organization.

They started with a retro and goal planning. From there, the team identified problem statements, looked for data supporting those problems, defined the impact they wanted to have, chose initiatives, built a roadmap, and assigned work across the squad.

That approach helped the team move quickly on things like transparent compensation, leveling, performance reviews, and promotion and merit processes.

The important shift is that HR isn’t starting with, “What program should we launch?” It’s starting with, “What problem are we trying to solve, and what evidence says it matters?”

“What’s the problem statement? What’s the data to support that problem statement? What’s the impact we wanna have?”

That operating model gives People teams permission to ship, learn, and improve instead of treating every new process like a permanent policy that has to be perfect on day one.

3. The People team of the future may be built around three archetypes

Jessica believes AI won’t simply make today’s People team more efficient. It could change the actual shape of the function.

She sees three profiles emerging.

The first is the care role: coaches, advisors, mentors, and people who help humans navigate work.

The second is the architect: someone building systems, workflows, integrations, HR technology, and AI-enabled infrastructure.

The third is the experience role: someone focused on the physical and communal parts of work — offsites, offices, events, learning days, and employee experiences.

For People leaders, that creates a practical talent-planning question: look at your current team and ask which of these capabilities you already have — and which ones you’re going to need to hire or develop.

4. Want your People team to ship faster? Consider hiring an engineer into it.

Leapsome’s People team has a forward-deployed engineer embedded directly with them. That allows Jessica’s team to move an idea from user research to a scrappy prototype, then hand it over for proper deployment, security, SSO, and integration into the broader tech stack.

The profile she looks for isn’t necessarily the most technically sophisticated engineer available.

She wants someone product-minded who cares about the use case, likes working closely with users, and is motivated by building simple, useful tools rather than massively scalable systems.

“I do not need this to be the most incredibly architected system that’s robust for ten million users. This is a system that is very much focused on usability and simplicity.”

One particularly interesting talent pool: engineers who are curious about people management but don’t currently have a management path. Working inside People Ops lets them learn how performance, feedback, leveling, and management systems actually work while applying their technical skill.

5. Move at full speed — but establish the guardrails with leadership first.

Jessica has a strong bias toward action. But joining a new organization creates a tension: you’re being hired for your experience and told to move quickly, while simultaneously needing to understand relationships, context, and how decisions get made.

Her solution has been to make the tradeoff explicit with leadership.

Rather than artificially slowing herself down, she tells Leapsome’s founders that she’s going to operate quickly — and asks them to pull her back if she crosses a boundary or starts creating unnecessary friction.

“You’re telling me move quickly, I am moving quickly. If you pull me back, I’m ready to be pulled back, but I need you to tell me.”

That’s a useful operating agreement for any executive entering a new company: clarify how much autonomy you actually have, define where leadership wants visibility, and agree on how they’ll signal when you need to slow down.

6. AI should remove HR work — not remove the human part of HR.

Jessica’s vision for AI in People Ops isn’t about replacing the conversations that matter. It’s about eliminating the manual work surrounding them.

She pointed to calibration as an example. AI can review feedback and scores, identify inconsistencies, flag potentially lenient or harsh managers, and build the pre-read before the calibration session even begins.

That means the People team spends less time assembling information and more time in the room helping managers make better decisions.

But Jessica also draws a clear boundary around where experimentation makes sense.

Use AI and vibe coding to build a leveling tool, an offsite workflow, a one-time assistant, or a highly specific internal process. Don’t casually rebuild the foundational system holding your most sensitive employee data.

The bigger opportunity is a more flexible People tech stack — one where HR can create workflows and tools around its core systems without waiting months for engineering resources or being trapped by rigid software.

And if that happens, People teams may finally get the kind of high-quality tooling commercial teams have had for years.

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