Senior Product Manager - AI Scheduling

About Aperture Cloud Aperture Cloud 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 Aperture Cloud process billions in annual payment volume, and see 65% more revenue using Aperture Cloud Payments by growing ticket size, rebooking clients at checkout, and saving on processing fees. About the Role Scheduling is the core engine of Aperture Cloud. 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. What You'll Do 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 Aperture Cloud 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 What We're Looking For 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 Benefits & Perks Competitive health & dental insurance options, effective on your first day of employment 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 professional development and continued learning High performers at 5 years receive a generous stipend to use however you recharge best 401k benefit: employees are eligible to contribute starting day 1 of employment Dependent Care FSA Paid parental leave Fertility and adoption benefits via Carrot and Kindbody The starting base salary for this role in New York is between $170,000 - $220,000 + target equity + benefits. The base salary offered is dependent upon many factors including skills, experience, location, and education. The base pay range is subject to change and may be modified in the future. At Aperture Cloud, we celebrate our differences and are committed to creating a workplace where all employees feel supported and empowered to do their best work. We believe this benefits not only our employees but our product, customers, and communit