Head of Onboarding and Professional Services; GTM Operations

Head of Onboarding and Professional Services (GTM Operations) 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 .

We’re looking for a Head of Onboarding and Professional Services Operations to lead and empower our Subscription Sales Onboarding Center of Excellence. This is a second-line leadership role leading 12 People Empowerers (managers) and ~115 individual contributors. You will play a pivotal role in shaping how Gusto supports prospects and customers during onboarding, driving operational excellence, and ensuring our sales and onboarding teams deliver consistently outstanding experiences.

This is an opportunity to be at the forefront of innovation leveraging AI and other digital-first onboarding solutions, driving efficiency and effectiveness for SMB prospects. Additionally, this leader will evolve our onboarding and implementation services for mid-market and Enterprise clients, ensuring consistent partnership and collaboration to deliver seamless migrations to Gusto’s people platform. This leader will be an active Amplifier of Gusto's AI-native strategy, directly shaping how our high-volume services use emerging technology for both scale and quality.

The Onboarding Center of Excellence (OCE) team sits within Subscription Sales and is focused on helping new customers onboard successfully. The team covers:

• Jr. Onboarding: High-velocity inbound phone and chat support for Direct and Gusto Pro (GPro) prospects.
• Onboarding Associates: Outbound support for dedicated seller prospects.
• Specialized Onboarding: Implementations and high Annual Contract Value (ACV) pod support.
• Senior Onboarding: Solution engineering and enterprise sales support.

Our mission is to deliver seamless, scalable onboarding experiences that empower customers and sellers alike.

• Lead and coach a team of 12 People Empowerers managing ~115 onboarding specialists.
• Drive excellence across inbound, outbound, specialized, and enterprise onboarding functions.
• Foster a culture of accountability, continuous improvement, and customer‑first problem‑solving.
• Partner cross‑functionally with Growth, Revenue Operations, Sales, Partnerships, and Marketing to streamline processes and drive growth.
• Leverage data and reporting tools to identify opportunities, measure impact, and improve team efficiency and effectiveness.
• Champion new ideas and solutions, helping shape the future of onboarding at Gusto by ushering in new AI capabilities. You will act as an Amplifier by defining and communicating new standards for service efficiency and quality across the entire onboarding team.
• Proactively embed AI into core workflows (e.g., automated response generation, data validation, and agent support tools). You must establish and coach best practices for the 4
  
  Gs across the team:
• Give it to AI
  :
  Use AI for high‑volume, low‑risk, repeatable tasks so people can focus on judgment, relationships, and outcomes.
• Guide the AI
  :
  Provide clear context, goals, tone, and examples so outputs are useful, on-brand, and aligned.
• Grade the Output
  :
  Treat AI as a first draft: verify accuracy, completeness, tone, compliance, and fairness before using or sharing.
• Guard the Trust
  :
  Protect privacy and security; earn confidence through transparency, quality, and ethical use.
• Model Gusto values by empowering people, encouraging dissenting opinions, and ensuring all voices are heard.

• 10+ years of relevant Operations experience (GTM Ops, Product Ops, Implementation, Professional Services), including 5+ years leading teams and leaders, with a track record of building high‑performing organizations and driving operational transformation at scale.
• Deep experience building and scaling onboarding and…