Senior Strategy & Operations 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 The Strategy and Operations team at GlossGenius sits at the center of the most important decisions the business is making, translating ambiguous problems into clear plans and getting them executed. In this role, you'll start by owning the strategy and execution for how GlossGenius onboards, retains, and grows a larger, more complex customer base — an important and greenfield problem. But the scope doesn't stop there. As you demonstrate impact, you'll take on other strategic initiatives across the business, wherever the most important work is. The role requires strong analytical instincts, clear thinking under ambiguity, and the ability to move from problem framing through execution without needing a fully defined brief. Domain expertise in Customer Success is not a prerequisite. We're looking for someone who can tackle hard business problems from first principles and build durable solutions, regardless of the function. You will report to the Chief Revenue Officer. 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 Own the strategy and execution roadmap for how GlossGenius onboards, retains, and grows its larger customer segment, spanning onboarding design, early lifecycle engagement, and account expansion Define the operational model for the Onboarding Specialist team, including day-to-day workflows, capacity planning, and how the org should evolve as the customer segment scales Build the analytics layer that tracks CS performance including onboarding conversion, time-to-value, expansion rates, and retention by segment, translating that data into decisions Evaluate the economics and opportunity costs of competing initiatives, determining where to invest, what to deprioritize, and how to sequence the build Design and run experiments across onboarding, lifecycle, and expansion plays, building a learning cadence that compounds over time Design AI-powered workflows that automate repeatable work across the CS motion including health monitoring, lifecycle triggers, and reporting, so the team's time stays on high-value interactions Align Sales, Product, Marketing, and CX on the operational requirements and cross-functional dependencies that make the CS motion work, then move on to the next high-priority problem As the CS motion matures, you will take on other high-priority strategic initiatives across the business What We’re Looking For 6+ years of experience in strategy, operations, business analysis, or strategic finance, with a track record of tackling ambiguous problems and building durable solutions rather than executing against defined playbooks You’ve built AI-powered workflows that changed how a function operates, automating repeatable work and redirecting capacity toward higher-judgment problems Comfortable building from scratch with minimal direction, making calls on structure and approach in problem spaces where the answer isn't obvious and the brief isn't fully written Strong analytical foundation, including fluency with modeling and data tools, and the ability to move from raw data to a clear strategic recommendation independently Proven ability to drive alignment and influence without direct authority across Sales, Product, Marketing, and Finance Clear written com