Manager, Customer Success

About GlossGenius GlossGenius is the AI-powered system behind the world's most meaningful appointments, helping 120,000+ service businesses earn more revenue and free up time for the work they love. Our agentic workforce gets more clients in the door, grows profit per appointment, and keeps clients coming back — doing the jobs owners never had time for and couldn't justify hiring to fill. Businesses on GlossGenius process billions in annual payment volume, and see 65% more revenue using GlossGenius Payments by growing ticket size, rebooking clients at checkout, and saving on processing fees. About the Role GlossGenius's customer base is growing fast, and our post-sales experience will be a real competitive differentiator. In this role, you'll lead the team of Onboarding Specialists responsible for getting high-revenue customers live on the platform, and you'll help to architect our broader Customer Success motion as we scale. You'll define what great looks like, from team structure to engagement strategy to the AI-powered workflows that make the whole operation run more effectively. This is a player-coach role that requires strong management instincts and a builder's orientation: you'll need to be in the work while simultaneously designing the system around it. You will report to the Director of Revenue Operations. You must be commutable to our NYC headquarters and will operate in an in-person environment. We default to being in-office 3–4 days per week with required attendance on Tuesdays and Thursdays. What You'll Do Lead, coach, and develop a team of Onboarding Specialists through data migration, payments setup, and product enablement for high-value accounts, holding a high bar for what excellent onboarding looks like Design and deploy AI-powered workflows across the CS motion, including automated health monitoring, churn signal detection, and onboarding automation, so the team's time stays concentrated on high-judgment relationship moments Own the post-sales engagement roadmap, designing a customer journey that moves beyond just onboarding toward sustained product adoption, expansion, and long-term retention Define and track KPIs including Time-to-Value, Net Retention, and customer health scores, using those signals to course-correct before issues become fires Partner with Sales and Account Executives to close the gap between closed-won and active-user, and surface product feedback to reduce churn before it becomes a pattern Serve as the escalation point for complex technical or relationship challenges on high-revenue accounts What We're Looking For 4+ years of experience in Customer Success or Onboarding, with at least 2 years leading teams at a high-growth technology company Experienced builder of AI-powered workflows in a CS or onboarding context, automating health monitoring, churn signals, or onboarding communications, and understands the difference between using a tool and redesigning how the function operates around one You move quickly and course-correct without waiting for full clarity, more comfortable shipping a v1 and iterating than spending weeks on alignment before starting Proven ability to lead a team through a meaningful operational shift, including new tools or workflows, and able to effectively bring people along without losing momentum on the work itself Comfortable using data to run a CS org, including health scores, retention trends, and TTV benchmarks, and can translate that analysis into decisions rather than just reports Has worked closely with Sales and understands that CS at a high-growth company is a revenue function, not a support function Benefits & Perks Competitive health & dental insurance options, effective on your first day of employment Flexible PTO In-office lunch twice per week for NYC and SF employees, plus late night dinner stipends Access to Wellhub, a corporate wellness platform with discounted gym memberships, fitness classes, and mental health resources Annual stipend for profess