Director of Product

As Director of Product, your mission is to build the premier product organization in supply chain: disciplined about what you build, iterative in how you build it, obsessed with the customer, and driven by data at every decision.
About Bobtail

Bobtail is dedicated to increasing happiness by eliminating inefficiencies in the supply chain. We envision a supply chain without friction, fraud, waste, and abuse where companies succeed based on the value they create.

We work in a unique way at Bobtail , where we value teams over individuals and encourage experimentation and iteration to constantly improve. Teams are given flexibility in working towards a shared purpose and given the freedom to decide how they will accomplish their goals.

If you are an out of the box thinker that takes a proactive approach in collaborating with others to solve problems and achieve your goals - we would love to talk to you.
The things we value:

- Mission

- Teams over individuals

- Collaboration

- Communication

- Iteration

- Experimentation and failing fast

- Initiative and solutions oriented approach

- Documentation

- Data

- Mental health and work life balance

- Diversity

- Transparency

We're hiring a Director of Product to lead product strategy, development, and innovation at Bobtail . This is a first-of-its-kind seat built around three priorities: deciding what Bobtail builds, deciding what it deliberately does not build, and executing at a high level in lockstep with engineering and the rest of the senior management team to ship it. You'll work directly with the CEO to turn a wide set of strategic options, into a sequenced, evidence-backed roadmap.

The ideal candidate has led product at a company of comparable size and complexity, with a track record of setting strategy from ambiguity rather than just running an existing roadmap, and the discipline to say no as often as yes. This individual will be highly data-driven and analytical, with the judgment to move on conviction when the data is inherently thin. We are looking for a strong product leader who can build the product management function at Bobtail from the ground up, hire and develop a team, and partner closely with engineering, design, and go-to-market leadership to turn decisions into shipped product. This includes identifying new products, services, platform capabilities, and revenue opportunities that solve meaningful problems for our customers and strengthen our competitive position. The right person will not wait for someone to hand them a list of features to build. They will spend time understanding how our customers operate, where they struggle, what they currently pay others to do, and what problems remain unsolved.
You should apply if you have:

- 8+ years of experience in product management and strategy, including experience leading product at a company of comparable size and complexity.

- A track record of setting product strategy from ambiguity and defending sequencing decisions with both data and judgment.

- Experience in fintech, financial services, payments, lending, factoring, transportation technology, or another transaction-heavy financial environment strongly preferred.

- Experience conducting product discovery, customer research, and market analysis. Strong commercial instincts and the ability to evaluate product opportunities based on customer value and business economics.

- Comfort with compliance and risk constraints (KYC/KYB, lending, payments) is a plus.

- Experience building and leading a product team, including hiring the first few members of a function.

- Strong technical fluency - you don't need to write code, but you should be able to work closely with engineering on architecture trade-offs and technical feasibility.

- Highly analytical and data-driven, with strong pattern-recognition and problem-solving skills.

- A bias toward shipping and iterating over long planning cycles.

- Comfort operating at a founder-led, profitable comp