Gusto
Head of Onboarding and Professional Services, Subscription Sales
Gusto, Denver, Colorado, United States, 80285
Overview
Head of Onboarding and Professional Services, Subscription Sales. Lead and empower the Onboarding Center of Excellence within Subscription Sales, guiding 12 People Empowerers (managers) and ~115 onboarding specialists. Shape how Gusto supports prospects and customers during onboarding, drive operational excellence, and ensure consistently outstanding experiences for sales and onboarding teams. 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 operates offices in Denver, San Francisco, and New York and serves 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 the Onboarding Center of Excellence in support of our Subscription Sales onboarding efforts. This second-line leadership role will evolve onboarding and implementation services for mid-market and Enterprise clients, ensuring seamless migrations to Gusto’s people platform and driving efficiency through AI and digital-first onboarding solutions. 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. 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 with AI-enabled approaches. Model Gusto values by empowering people, encouraging dissent, and ensuring all voices are heard. What We're Looking For
10+ years of relevant Sales Implementation and Onboarding experience, including at least 5+ years leading teams and leaders. Experience scaling onboarding and implementation organizations using chat tools, tiered pricing options, and collaboration with workforce management teams. AI fluidity and curiosity — eagerness to learn the most effective ways to leverage AI within 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 demonstrated success in diverse, fast-paced roles. Experience building, adapting, and scaling sales and onboarding teams in high-growth environments. Compensation
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. Location & Office Expectations
Gusto has offices in Denver, San Francisco, and New York City. Employees 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 expectations apply to all Symmetry roles, Gusto’s subsidiary in Scottsdale. When approved to work remotely, a secure, reliable internet connection is required. Equal Opportunity
Gusto is 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 legally protected characteristics. Gusto considers qualified applicants with criminal histories in line with applicable laws. We provide reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you require accommodations, please contact us. Privacy & Security
Gusto takes security and protection of personal information seriously. Please review our Fraudulent Activity Disclosure and Applicant Privacy Notice.
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Head of Onboarding and Professional Services, Subscription Sales. Lead and empower the Onboarding Center of Excellence within Subscription Sales, guiding 12 People Empowerers (managers) and ~115 onboarding specialists. Shape how Gusto supports prospects and customers during onboarding, drive operational excellence, and ensure consistently outstanding experiences for sales and onboarding teams. 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 operates offices in Denver, San Francisco, and New York and serves 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 the Onboarding Center of Excellence in support of our Subscription Sales onboarding efforts. This second-line leadership role will evolve onboarding and implementation services for mid-market and Enterprise clients, ensuring seamless migrations to Gusto’s people platform and driving efficiency through AI and digital-first onboarding solutions. 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. 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 with AI-enabled approaches. Model Gusto values by empowering people, encouraging dissent, and ensuring all voices are heard. What We're Looking For
10+ years of relevant Sales Implementation and Onboarding experience, including at least 5+ years leading teams and leaders. Experience scaling onboarding and implementation organizations using chat tools, tiered pricing options, and collaboration with workforce management teams. AI fluidity and curiosity — eagerness to learn the most effective ways to leverage AI within 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 demonstrated success in diverse, fast-paced roles. Experience building, adapting, and scaling sales and onboarding teams in high-growth environments. Compensation
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. Location & Office Expectations
Gusto has offices in Denver, San Francisco, and New York City. Employees 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 expectations apply to all Symmetry roles, Gusto’s subsidiary in Scottsdale. When approved to work remotely, a secure, reliable internet connection is required. Equal Opportunity
Gusto is 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 legally protected characteristics. Gusto considers qualified applicants with criminal histories in line with applicable laws. We provide reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you require accommodations, please contact us. Privacy & Security
Gusto takes security and protection of personal information seriously. Please review our Fraudulent Activity Disclosure and Applicant Privacy Notice.
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