Head of AI-Native Talent Systems

About the Role:

Gusto is looking for a builder to take on the role of Head of AI-Native Talent Systems as we rethink how people grow in an AI-native company. This role is about designing the systems that shape growth day to day. Not courses. Not programs. The actual mechanics of work. Onboarding, feedback, performance reviews, promotion decisions, and leadership expectations should all help people get better by default, without needing special events or extra effort. You will be responsible for building new architecture and tearing down what no longer serves us. AI will be a core part of how you do this, not as a concept, but as a practical tool for reflection, coaching, skill building, and clarity. The goal is simple but hard: make growth obvious, continuous, and hard to avoid. This is a role for someone who wants to build something durable, test it in the real world, and keep improving it. If it works, others will copy it. If it doesn’t, you’ll learn fast and fix it.

About the Team:

The Talent Development team sits within the Gustie Engagement Team, with a shared purpose: to help Gusties write the best chapters of their careers. We do this by designing the conditions that create clarity, connection, and commitment across the employee journey, not through programs, but through how work actually happens.

Here’s what you’ll do day-to-day:

(The day-to-day will change. That’s part of the job.)

• Own the Gustie growth system at Gusto, from onboarding through executive leadership, with AI embedded at its core


• Redesign moments like feedback, performance reviews, and promotion decisions so AI actively helps people reflect, learn, and improve in real time


• Treat AI as a design partner in growth, deciding deliberately where it should lead, where it should support, and where humans stay firmly in charge


• Build development directly into the flow of work, with AI reducing friction, surfacing insights, and prompting better decisions


• Prototype, test, and ship AI-enabled changes that meaningfully improve how people grow here


• Define new AI-native standards for leadership development, coaching, and skill building


• Create feedback loops and signals, powered by AI, that make growth, readiness, and leadership effectiveness visible as the company evolves


• Continuously revisit what belongs in code, what belongs in judgment, and how the boundary should shift over time

Here’s what we're looking for:

(If you’ve done this before, you’ll recognize yourself.)

• You’ve built something that changed how people actually worked. It might have been called talent, product, systems, or something else entirely, but it moved behavior, not just decks.


• You believe the walls are hollow and you don’t assume systems are fixed just because they look finished.
  You get impatient with patchwork solutions and prefer fixing the system instead.


• You’re comfortable starting without a playbook and writing one as you go.


• You already use AI as part of how you think and work, not as a talking point or side project.


• You can hold a long-term point of view while shipping fast and putting real things into the world.


• You have strong opinions about what good looks like, and you’re willing to change them when reality disagrees.


• You care deeply about how people grow, especially when things are changing quickly or breaking in interesting ways.

People who fit this role often have 10–12 years of relevant experience, but we care far more about what you’ve built than how your resume is labeled.

What does success look like?

A year into this role, growth at Gusto is no longer something people are asked to manage on top of their jobs. It is something the company’s systems quietly and consistently do. The everyday work of the company generates signal by default. Decisions, docs, code, customer interactions, feedback, and leadership moments all leave usable traces. Those signals are captured and interpreted as work happens, then reflected back in ways that help people see patterns, progress, and gaps without needing to reconstruct the past or advocate for themselves. Growth becomes legible. Learning is no longer organized around classes, curricula, or moments on a calendar. Instead, it exists as an always-on environment woven into how work gets done. People can quickly see examples of strong judgment, understand what “good” looks like in context, and explore how similar problems have been solved before. AI makes this possible at scale by synthesizing real examples, answering questions in the moment, connecting people to relevant expertise, and turning individual insight into shared capability. Over time, development feels less like an intervention and more like a natural byproduct of doing the work. People pull what they need when they need it. Leaders spend less time explaining expectations and more time reinforcing them. The system improves with use, because every interaction adds clarity rather than noise. Importantly, the system has a point of view. It creates gentle pressure in the right places and removes friction in the wrong ones. It makes certain behaviors easier, others harder, and does so through design rather than persuasion. Standards become clear not because they are stated repeatedly, but because the environment reinforces them. At that point, this work no longer resembles traditional Talent Development or Performance Management. It looks like core infrastructure for a company that expects to keep changing, and expects its people to keep pace not through heroics, but through design.

Our cash compensation amount for this role is $150,000 /year to $180,000 /year in Denver & most major metro locations, and $177,000/year to $210,000 /year for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the amounts listed above.