Gusto · 12 hours ago
Head of Onboarding and Implementation (GTM Operations)
Atlanta Metro
Full-time
Hybrid
Director/Executive
$250K/yr - $293K/yr
10+ years expGusto is on a mission to grow the small business economy by handling payroll, health insurance, and HR services. They are seeking a Head of Onboarding and Implementation to lead their Subscription Sales Onboarding Center of Excellence, focusing on driving operational excellence and enhancing customer onboarding experiences.
Bookkeeping and PayrollEmployee BenefitsEnterprise SoftwareFinancial ServicesFinTechHuman ResourcesSaaSSoftware
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 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
Qualification
Required
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
Benefits
Health insurance
401(k)
Company
Gusto
Gusto is an HR and payroll platform that simplifies complex tasks, empowering businesses to focus on what matters most.
1001-5000 employees
H1B Sponsorship
Gusto has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (49)
2024 (54)
2023 (19)
2022 (37)
2021 (24)
Funding
Current Stage
Late StageTotal Funding
$746.1MKey Investors
Friends & Family CapitalT. Rowe PriceAkkadian Ventures
2023-01-28Series Unknown
2022-05-12Series E· $55M
2021-08-10Series E· $175M
Leadership Team
Josh Reeves
Head of Gusto (CEO) and Co-Founder. Building Gusto for the Long Term.
Edward Kim
Co-founder and Head of Technology
Recent News
Small Business Trends
2026-01-12
General Catalyst
2025-12-30
Digital Commerce 360
2025-12-20
Company data provided by crunchbase