Senior Product Manager, Booking Experience

Help customers turn an experience they want into a plan they can rely on. Whether someone is checking dates before buying or arranging a visit after purchase, they need to know what fits, secure a suitable time and trust that the booking will be honored.

You will be the hands-on business owner for bookability, combining product management, AI building and go-to-market. Given a business target, test several approaches in parallel: partner integrations, booking tools, booking agents or another practical route. Run short learning cycles, ship quickly and put effort behind what works.

Work across merchant-managed and partner-connected supply, with dependable availability and accurate confirmation behind every customer promise. Lead commercial discussions with potential booking providers. Understand the merchant's incentives, habits and workload so the solution earns adoption and sustained use.

This is a hands-on senior individual-contributor role. You will lead the area's product direction, prototype, work closely with engineers in the Czech Republic and make decisions with product leadership across time zones. AI is a core tool in how we work and an important part of the product direction. Use it where it improves outcomes, with evidence behind every customer promise.

• →Lead improvement of the booking journey: understand requirements, find suitable availability, secure and confirm a reservation, manage changes and arrive prepared.
• →Diagnose customer friction using raw funnels, session behavior, customer research and support evidence. Separate the symptoms from their possible causes.
• →Make dependable availability practical for merchants, including paper-based businesses. Test whether self-service tools, integrations or booking agents best fit their habits, capacity and workload.
• →Own product adoption and GTM with Commercial and Merchant Operations: target cohorts, value proposition, distribution, launch sequencing, activation and repeat use. Build a credible route to less digitally confident merchants.
• →Work with Engineering and Connectivity on consistent availability and product rules, and with Checkout and Post-Purchase on handoffs, confirmations and booking management.
• →Lead commercial negotiations with booking providers: pricing, service terms, commitments and merchant economics. Compare partnering with building or using booking agents.
• →Define booking success, reliability, merchant effort and financial contribution. Keep distinct journeys and supply types measurable, with clear denominators and quality guardrails.
• →Build and test AI-enabled workflows alongside other options. Evaluate accuracy, recovery, cost and value; scale what works and stop weak approaches quickly.

• Typically 6+ years in product management, or equivalent founder/operator ownership, in marketplaces, booking, scheduling, e-commerce or small-business software.
• Proven adoption and GTM experience: personally took a product from target-segment and value-proposition decisions through launch, activation and sustained use. Show measurable uptake and how you adapted when adoption fell short.
• Hands-on AI building: prototype, test and ship working solutions. Run several low-cost experiments in parallel and change direction quickly as evidence changes.
• Strong product judgment across customer and merchant needs. You simplify difficult tasks while keeping important conditions and uncertainty visible.
• Fluency in SQL, funnels, cohort analysis and experiments, combined with direct customer evidence. You distinguish observed behavior from inferred causes.
• Experience shipping and evaluating AI-enabled or automation features, including monitoring, fallbacks and cost. Fluency with AI tools in your own product work.
• Experience leading commercial negotiations with providers or partners. Evaluate pricing, commitments, service terms, margin and operating cost against the business target.
• Clear communication and independent ownership. Present a recommendation, defend the details, respond constructively to challenge and keep delivery moving with limited synchronous overlap.

Strong profile signal: founder or small-company experience combining product, AI building, GTM and commercial ownership. Relevant domains include appointments, activities, ticketing, reservations and calendar integrations.

Agree a business target and initial journey/cohort, then test several approaches in parallel within available capacity. Use short learning cycles to decide what to ship or scale. These milestones are review points, not a fixed quarterly solution plan; commitments depend on baselines, access and staffing.

• Week 1: understand the customer and merchant jobs, inspect the existing journeys and evidence, and identify a focused first opportunity with the team.
• Week 2: aim to ship one bounded improvement to an existing flow, with instrumentation and a clear quality bar. Establish any delivery dependency immediately.
• 30 days: have a first improvement live and bounded parallel tests underway, with a cohort, value proposition, launch route and adoption measures.
• 60 days: compare reach, activation, repeated use and economics across tested approaches; scale, revise or stop them. Evaluate AI against simpler alternatives.
• 90 days: quantify mature outcomes and costs. For outcomes not yet observable, report the gaps and next observation window. Set the next priorities, including the path to merchants with less digital experience where relevant.

Success is dependable booking and sustained merchant use. A shipped interface, a calendar connection or a compelling prototype is a means of getting there.