Senior Product Manager - AI Scheduling

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.

Scheduling is the core engine of GlossGenius. Every appointment booked is direct revenue for our customers and for us, which makes it one of the highest-leverage product surfaces on the platform. As a Senior PM for Scheduling, you'll own the roadmap that determines how 120,000+ appointment-based businesses fill their books: from the calendar infrastructure providers rely on every day to the AI-powered scheduling tools that are just getting started. There's no playbook to inherit here. You'll define what's next, make the calls that balance platform stability against new capability, and ship work that directly moves GMV and provider retention.

You will report to the Director of Product. 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.

• →Own the Scheduling roadmap end-to-end: prioritize across platform reliability, new capabilities, and AI-powered features 
• →Ship the mobile calendar to full general availability and then define what comes after: performance, intelligence, and the calendar experience that sets GlossGenius apart from every generic scheduling tool
• →Translate how appointment-based businesses actually want to run their schedules into product logic that works at scale across diverse business types
• →Define and ship AI-native scheduling experiences, from intelligent availability surfacing to agentic rebooking flows that put real time back in providers' hands
• →Build a continuous improvement loop across booking volume, calendar utilization, and AI engagement metrics, diagnosing what's driving movement and acting on it faster than anyone expects
• →Partner with Engineering, Design, and GTM to bring complex, infrastructure-heavy features to market with clarity and speed

• 5+ years of product management experience, with a track record of owning complex, high-impact product areas at a high-growth technology company, ideally with experience in scheduling, calendar, marketplace, or workflow-automation products
• Shipped AI-powered features or redesigned your team's research and decision-making workflows around AI tooling, with a clear point of view on where AI creates leverage in a product and proof that you've built something real with it
• Strong analytical instincts: you go to the data before you go to the meeting, you can distinguish a signal from noise, and you use quantitative and qualitative inputs together to drive prioritization
• Technical fluency: comfortable in the weeds of a complex domain model, able to hold your own in architecture conversations, and skilled at translating platform constraints into clear product tradeoffs
• Experience bringing platform or infrastructure-adjacent products to market, where the challenge isn't just what to build but sequencing what can be built given real technical dependencies
• You actively look for the repeatable parts of your job, automate what shouldn't require judgment, and redirect your focus toward the decisions that actually do