Staff Product Manager, Transactions & Trust

Collaborative Boating operates Boatsetter and GetMyBoat, two marketplaces connecting guests with captains, operators, and boat owners. The Staff Product Manager will own the full transactions and trust experience, including checkout, payments, payouts, fees, insurance, credits, disputes, and reviews, while shaping strategy, influencing cross-functional teams, and mentoring PMs.

Responsibilities:

• The full money path, and the strategy behind it. You'll own every step from "Book Now" through financial settlement: checkout, payments, payouts, fees, insurance, credits, and dispute resolution, across both brands, web and mobile. You'll turn a proposed sequence of what's left to build into a strategy the company commits to, and revise it when the evidence says you should
• Insurance, as a product and a program. You'll decide where we stand on insurance by region, how coverage is verified, how it's priced into an order, and how it works outside the US. These are decisions with legal, financial, and partner consequences. You'll frame them, get them made, and deliver on them
• Fees that people understand. You'll build a fee structure the business can adjust, and a breakdown that shows guests and operators exactly where every dollar goes, before they pay and after they're paid
• Credits, changes, and disputes. You'll own what happens when a trip changes, a guest is owed something, or the two sides disagree about what was promised
• Reviews on one platform. You'll lead the move to a single review system across both brands, so reputation earned on one carries over to the other
• Core business outcomes. Examples include checkout conversion, payment success, payout accuracy and timing, dispute rates, and the share of transactions that stay on-platform. Many of them depend on teams you don't run
• The hard tradeoffs. Guest protection against operator fairness, transparency against conversion, flexible policy against predictable revenue
• Influence beyond the pod. The money path only works if finance, operations, support, insurance partners, and the rest of product work with it. You'll shape their roadmaps through clear reasoning and shared goals, not escalation
• A stronger PM practice. You'll mentor other PMs, help shape how we hire, and improve the way product work gets done here

Requirements:

• Owned strategy for checkout, payments, or payouts in a two-sided marketplace with company-level impact
• Hit ambitious OKRs that crossed team lines
• Unblocked a decision with real stakes
• Made pricing or fees transparent without losing revenue
• Designed policy as product
• Made the PMs around you better, through mentorship, hiring, or fixing how the team works
• Remote, with high overlap with US Eastern hours
• Insurance products, embedded insurance, or coverage verification, especially across regions or countries
• Hands-on experience with payment processors, marketplace payouts, or split payments
• Building configurable fee or pricing systems
• Chargeback and dispute operations
• Migrating live transactions between platforms without breaking bookings in flight
• Review and reputation systems
• Travel, rentals, or local-services marketplaces at scale
• Comfort pulling your own data
• Relevant degrees are welcome and not required