Head of Gustie

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k) s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve.

Learn more about our Total Rewards philosophy.

Gusto is looking for a builder to take on the role of Head of Gustie Growth 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.

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.

• 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

• 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.

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…