Gusto
Head of Onboarding and Professional Services, Subscription Sales
Gusto, New York, New York, us, 10261
Head of Onboarding and Professional Services, Subscription Sales
Join to apply for the
Head of Onboarding and Professional Services, Subscription Sales
role at
Gusto .
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 we’re committed to building a collaborative and inclusive workplace, both physically and virtually.
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 shape how Gusto supports prospects and customers during onboarding, drive operational excellence, and ensure our sales and onboarding teams deliver outstanding experiences. You will leverage AI and digital onboarding solutions to drive efficiency and effectiveness for SMB prospects and will evolve our onboarding and implementation services for mid-market and Enterprise clients to ensure seamless migrations to Gusto’s platform.
About The Team
The Onboarding Center of Excellence (OCE) sits within Subscription Sales and focuses on helping new customers onboard successfully. The team covers:
Jr. Onboarding: High-velocity inbound phone and chat support for Direct and Gusto Pro 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 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 to shape the future of onboarding at Gusto and explore AI-enabled improvements.
Model Gusto values by empowering people, encouraging dissent, 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.
Experience building and scaling onboarding and implementation organizations leveraging chat tools, tiered pricing options, and collaboration with workforce management teams.
AI fluency and curiosity — a leader eager to learn effective ways to leverage AI in the customer onboarding journey.
Strong initiative with a track record of ownership and 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 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.
Work Location and Office Expectations Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days (approximately 2-3 days per week, or more depending on role). Office expectations also apply to Gusto’s subsidiary, Symmetry, based in Scottsdale. Note: The San Francisco office expectations cover the SF and San Jose metros. When approved to work from a location other than a Gusto office, a secure, reliable internet connection is required.
Equal Opportunity 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, pregnancy, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, or any other legally protected characteristic. We consider qualified applicants with criminal histories in accordance with applicable law. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.
Gusto takes security and protection of personal information seriously. Please review our Fraudulent Activity Disclaimer and our Applicant Privacy Notice.
Referrals increase your chances of interviewing at Gusto.
New York, NY
#J-18808-Ljbffr
Head of Onboarding and Professional Services, Subscription Sales
role at
Gusto .
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 we’re committed to building a collaborative and inclusive workplace, both physically and virtually.
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 shape how Gusto supports prospects and customers during onboarding, drive operational excellence, and ensure our sales and onboarding teams deliver outstanding experiences. You will leverage AI and digital onboarding solutions to drive efficiency and effectiveness for SMB prospects and will evolve our onboarding and implementation services for mid-market and Enterprise clients to ensure seamless migrations to Gusto’s platform.
About The Team
The Onboarding Center of Excellence (OCE) sits within Subscription Sales and focuses on helping new customers onboard successfully. The team covers:
Jr. Onboarding: High-velocity inbound phone and chat support for Direct and Gusto Pro 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 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 to shape the future of onboarding at Gusto and explore AI-enabled improvements.
Model Gusto values by empowering people, encouraging dissent, 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.
Experience building and scaling onboarding and implementation organizations leveraging chat tools, tiered pricing options, and collaboration with workforce management teams.
AI fluency and curiosity — a leader eager to learn effective ways to leverage AI in the customer onboarding journey.
Strong initiative with a track record of ownership and 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 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.
Work Location and Office Expectations Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees based in those locations are expected to work from the office on designated days (approximately 2-3 days per week, or more depending on role). Office expectations also apply to Gusto’s subsidiary, Symmetry, based in Scottsdale. Note: The San Francisco office expectations cover the SF and San Jose metros. When approved to work from a location other than a Gusto office, a secure, reliable internet connection is required.
Equal Opportunity 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, pregnancy, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, or any other legally protected characteristic. We consider qualified applicants with criminal histories in accordance with applicable law. We are committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures.
Gusto takes security and protection of personal information seriously. Please review our Fraudulent Activity Disclaimer and our Applicant Privacy Notice.
Referrals increase your chances of interviewing at Gusto.
New York, NY
#J-18808-Ljbffr