Staff Product Manager, Transactions & Trust

Staff Product Manager, Transactions & Trust

Company

Collaborative Boating operates Boatsetter and GetMyBoat, the two largest marketplaces for getting on the water, now converging into one platform. Guests arrive wanting something specific, like a fishing trip, a sunset cruise, or a birthday on a pontoon. We connect them to the captains, operators, and owners who can make it happen. Finding and booking a day outside should be as easy and intuitive as booking a flight.

The problem

Every booking is a promise between strangers. A guest pays in advance for a day that depends on weather, a captain, and a boat. An operator hands over something worth more than a house to someone they've never met. Between "Book Now" and the operator getting paid, a lot has to go right. The price has to be clear, fees have to be explained, insurance has to be in place, credits and changes have to be handled, and disputes have to be resolved fairly.

Our mission is simple to say and hard to do. Every dollar on the platform should move accurately, on time, and transparently enough that everyone involved trusts us more after each transaction than before it. Today that path runs across two legacy brands and is being rebuilt as one platform. There’s a wealth of historical data, context and learnings to draw from. What's left are the decisions: how insurance should work across regions, what a guest should see before paying, and how fees should be structured so they're fair to both sides and sustainable for the business. These decisions are waiting on someone to own them.

What you'll own

• 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.

How we work

Problem, then system, then experience

We frame the problem first. Then we settle the shape of the system, meaning the entities, states, and constraints. Only then do we design the experience inside it. In this domain, the system is the product: what an order is, what it's made of, which states it can move through, and what money moves when it does. We map the domain in event-storming sessions, write behavior as concrete scenarios before building it, and record decisions in RFCs and architecture decision records. You'll help write them, not wait for them. If you're used to handing over a PRD and returning at launch, this will be frustrating.

Discovery is ongoing, not a handed off spec

You talk to guests and operators directly, every week, alongside your designer. You'll read the support queue, sit in on dispute reviews, and learn what a payout problem actually costs an operator. Discovery doesn't end in a slide deck. It ends in a decision, and when work stalls waiting for one, getting that decision made is your job.

We ask what moved, not what shipped

You define the signal before release and watch it after. Hitting the number you set is the minimum, not the goal. The work worth remembering beats it. In this domain, the results often show up late and in someone else's metrics. A clearer fee breakdown might show up in fewer support contacts, and a verification change might show up in claims months later. You need to know where to look. Sometimes the answer is that the bet didn't work. When that happens, you say so plainly, and we kill it.

We ship in days, not quarters

Work goes live the day it's ready. There's no launch calendar and no approval chain. The pod decides and it goes out. Moving money raises the standard for being ready, but it doesn't slow the cadence. That means guarded rollouts, reversible changes, and reconciliation you can trust, then the next slice. Your strategy sets the order of work, not a release schedule. It tells the pod which narrow, finished slice matters most this week, and why the next one follows.

We cross lines, and we bet on each other

Titles and team boundaries carry little weight here. You'll be in a finance close review, on a call with an insurance partner, talking to an operator whose payout went sideways, and helping discovery decide how fees and coverage should appear in search. Ask for help early and give it generously. The standing assumption is that the person next to you is good and worth backing before they've proven it, and we'll make the same assumption about you.

What you need to have done

• Owned strategy for checkout, payments, or payouts in a two-sided marketplace with company-level impact. You authored the strategy, not just executed it.
• Hit ambitious OKRs that crossed team lines. Walk us through one you set: how you knew it was ambitious, what you traded to get there, and what you did when it slipped.
• Unblocked a decision with real stakes. Pick one where legal, finance, partners, or leadership had to agree before the work could move. Tell us how you framed it, who disagreed, and what happened next.
• Made pricing or fees transparent without losing revenue. Tell us what you showed, what you held back, why, and what happened to conversion and trust afterward.
• Designed policy as product. You've treated cancellation, refund, credit, or dispute rules as something to build, test, and improve, not as legal text someone else wrote.
• Made the PMs around you better, through mentorship, hiring, or fixing how the team works.

What also helps

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. Each of these is a plus, not a requirement.

Practicals

Remote, with high overlap with US Eastern hours. You'll report to our Chief Product Officer, join a fully resourced product team with a dedicated designer, and be the dedicated PM in this pod. Relevant degrees are welcome and not required. A track record of shipped, measured work outweighs credentials.