Head of Onboarding and Implementation; GTM Operations

Position Overview

Head of Onboarding and Professional Services Operations at Gusto offers a unique opportunity to lead the Subscription Sales Onboarding Center of Excellence. At Gusto, we empower small businesses by handling payroll, benefits, HR, and more so that owners can focus on what they do best. With teams across Denver, San Francisco, and New York, we support over 400,000 small businesses and are committed to building a diverse and inclusive workplace. In this role, you will shape and drive operational excellence in onboarding, leveraging innovative AI solutions to enhance the customer experience and support both high-velocity and enterprise-level initiatives.

Key Responsibilities

• Responsibilities: Lead and coach 12 People Empowerers and approximately 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.
• Champion innovative ideas and modern AI capabilities to redefine onboarding standards and service quality.
• Embed AI into core workflows by implementing the four guiding principles: Give it to AI, Guide the AI, Grade the Output, and Guard the Trust.

Required Qualifications

• Experience Required: 10+ years of relevant Operations experience (GTM Ops, Product Ops, Implementation, Professional Services), including 5+ years of leadership experience managing teams and senior leaders.
• Qualifications: Proven track record in building and scaling onboarding and professional service functions for SMB, mid-market, or Enterprise clients.