Head of Onboarding and Professional Services, Subscription Sales

at Gusto, Inc.

Atlanta, Denver, New York, United States

About Gusto

Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses nationwide.

Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.

About the Role

We’re looking for a Head of Onboarding and Professional Services 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.

About the Team

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.

Here’s what you’ll do day-to-day

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, and Growth 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 ushering new AI .
Model Gusto values by empowering people, encouraging dissenting opinions, and ensuring all voices are heard.

Here’s what we're looking for

10+ years of relevant Sales Implementation and Onboarding experience, including at least 5+ years leading teams and leaders.
Familiarity with building and scaling onboarding and implementation organizations leveraging chat tools, tiered pricing options, and collaboration with workforce management teams.
AI Fluidity and curiosity - a leader eager to learn about the most effective and efficient ways to leverage AI within the customer onboarding journey.
Strong initiative: a track record of taking ownership, anticipating needs, accelerating progress of key initiatives
Ability to think critically, voice dissent with clear reasoning, and propose actionable solutions.
High accountability and a drive for excellence, with demonstrated success in diverse, fast-paced roles.
Experience building, adapting, and scaling sales and onboarding teams in high growth environments.

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 offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.