Head of Sales Onboarding and Implementation (GTM Operations) at Gusto

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.

About the Role

We’re looking for a Head of Sales Onboarding and Implementation 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. This leader will be an active Amplifier of Gusto's AI-native strategy, directly shaping how our high-volume services use emerging technology for both scale and quality.

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 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 capabilities. You will act as an Amplifier by defining and communicating new standards for service efficiency and quality across the entire onboarding team.

Proactively embed AI into core workflows (e.g., automated response generation, data validation, and agent support tools). You must establish and coach best practices for the 4Gs across the team:

Give it to AI: Use AI for high-volume, low-risk, repeatable tasks so people can focus on judgment, relationships, and outcomes.

Guide the AI: Provide clear context, goals, tone, and examples so outputs are useful, on-brand, and aligned.

Grade the Output: Treat AI as a first draft: verify accuracy, completeness, tone, compliance, and fairness before using or sharing.

Guard the Trust: Protect privacy and security; earn confidence through transparency, quality, and ethical use.

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 Operations experience (GTM Ops, Product Ops, Implementation, Professional Services), including 5+ years leading teams and leaders, with a track record of building high-performing organizations and driving operational transformation at scale.

Deep experience building and scaling onboarding and implementation organizations, including designing AI-driven onboarding journeys, chat-based support, personalized recommendations, and dynamic prospect flows. Experience overseeing key strategic levers such as incentive redesign, routing and prioritization logic, channel depth strategy, and workflow optimization to improve speed-to-value and conversion.

Bias to action and exceptional cross-functional partnership, able to collaborate closely with Growth, PMM, Workforce Management, CX, Sales, and Product teams to deliver a best-in-class, AI-first onboarding motion across both digital and human-assisted touchpoints. Comfortable navigating competing priorities, aligning stakeholders, and accelerating decision-making.

AI fluency and intellectual curiosity, with a demonstrated interest in learning, experimenting, and applying AI solutions to improve onboarding efficiency, accuracy, personalization, and customer outcomes. Able to partner with product and engineering teams to define requirements and test new AI capabilities.

Strong initiative and ownership, with a history of anticipating needs, identifying operational gaps, and leading high-impact initiatives end-to-end—from incentive structure modernization to routing and prioritization enhancements, lead-to-onboard flow redesign, and cross-channel strategy evolution.

Advanced critical thinking and constructive dissent, skilled at spotting the root cause of performance issues, challenging assumptions with clarity and data, and proposing actionable solutions that improve throughput, quality, and customer experience.

High accountability and a drive for excellence, proven in fast-paced, dynamic, or high-growth environments. Maintains elevated standards for team performance, operational predictability, and customer-facing outcomes.

Experience building, adapting, and scaling sales and onboarding teams, including hiring, training, coaching, and evolving team structures to fit changing product, channel, or customer needs. Familiarity with optimizing channel depth (digital, inside sales, outbound, franchises, accountants, BD) to ensure prospects and customers receive the right level of interaction at the right time.

Compensation Our annual OTE range for this role is $250,400 - $293,000 in San Francisco and 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.

Head of Sales Onboarding and Implementation (GTM Operations)

Job Description