Head of Onboarding and Professional Services, Subscription Sales

Position Overview

Gusto is a modern, online people platform that helps small businesses take care of their teams—from full-service payroll and health insurance to expert HR and team management tools. In this role as Head of Onboarding and Professional Services, you will lead the Subscription Sales Onboarding Center of Excellence, managing 12 People Empowerers and approximately 115 onboarding specialists. You will drive operational excellence and deliver consistently outstanding onboarding experiences by leveraging innovative digital and AI-driven solutions.

Key Responsibilities

• 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 initiatives.
• Model Gusto values by empowering people, encouraging dissenting opinions, and ensuring all voices are heard.

Required Qualifications

• 10+ years of relevant Sales Implementation and Onboarding experience, including at least 5+ years in leadership roles.
• Experience building and scaling onboarding and implementation organizations leveraging chat tools and tiered pricing models in collaboration with workforce management teams.
• AI Fluidity and curiosity – eagerness to learn and implement the most effective AI solutions within the customer onboarding journey.
• Strong initiative with a proven track record of ownership, anticipating needs, and accelerating key initiatives.
• Ability to think critically, voice dissent with clear reasoning, and propose actionable solutions.
• High accountability and a drive for excellence, demonstrated in diverse, fast-paced environments.
• Experience in building, adapting, and scaling sales and onboarding teams in high growth settings.

Benefits & Perks

• Compensation: Our annual OTE range for this role is $250,400 - $293,000 in New York, and $220,000 - $257,000 in Denver and Atlanta. Final offers are determined by candidate experience and expertise.
• Work from modern office spaces in Denver, San Francisco, and New York City with designated in-office days.
• Join a collaborative, inclusive, and innovative team committed to empowering its people and fostering growth.