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 company rather than a venture-subsidized one. Strong communication and cross-functional leadership skills, including the ability to clearly communicate product strategy and trade-offs to senior leadership. The discipline to say no - comfortable deferring or killing ideas that don't earn their place on the roadmap, even when they're compelling in isolation or popular internally. Demonstrated ability to influence across functions and challenge senior stakeholders constructively. Financial fluency - comfortable modeling and defending the revenue potential, development cost, and opportunity cost of a roadmap bet directly to the CFO and other finance stakeholders. A track record of measuring product success based on customer and business outcomes. An obsession with the customer and the product - you can't walk past something broken without wanting to fix it, and you know the product as well as the people using it, not just the roadmap slide. You will be responsible for: Decide What to Build: Develop and maintain a product strategy that clearly connects product investment to the company's broader strategic and financial objectives. Look beyond incremental feature improvements to identify opportunities for meaningful product innovation. Process around decision making: Create a disciplined process for gathering and evaluating ideas without allowing the product roadmap to become a collection of stakeholder requests. Ensure completed functionality solves the underlying customer or business problem rather than simply meeting documented requirements. Decide What Not to Build: Exercise real judgment about scope. Establish clear criteria for when to build, continue investing in a new product, change direction, or discontinue an initiative. Execute at a High Level: Partner closely with engineering - and with design, go-to-market, and senior leadership - to turn the roadmap into shipped product on a predictable cadence, not just a plan. Defend the Business Case: Build and defend the revenue potential, development cost, and opportunity cost of each major roadmap bet to the CFO, so product decisions hold up under financial scrutiny, not just strategic conviction. Own the outcome: Ensure new products have clearly understood operational, financial, regulatory, and risk requirements before launch. Measure product success based on business outcomes - not simply whether features were delivered. Own the Product: Take full, unbounded ownership of Bobtail's product. There are no lanes here; if it touches the customer or the platform, it's yours to shape. Obsess Over the Customer and the Product: Establish a disciplined process for identifying and evaluating new product opportunities. Spend meaningful time talking directly with customers rather than relying exclusively on feedback filtered through Sales or Operations. Develop a strong understanding of competitors and adjacent providers within transportation finance and fintech. Live inside the carrier's day-to-day and inside the product itself. We want someone who can't walk past something broken without wanting to fix it, and who knows the product as well as the people using it. Evidence-Driven Decision Making: Build the muscle - data, customer research, experimentation - to validate bets before committing engineering resources, while being willing to move on conviction when the data is inherently thin. Team Building: Hire and develop the product management function at Bobtail, defining process and hiring bar as the first dedicated product leader. Market & Competitive Judgment: Track how freight-tech and fintech infrastructure are evolving, including AI-driven disruption and industry consolidation, and stress-test Bobtail's roadmap against it. Benefits Generous PTO Monthly Mental Break Day Parental leave Comprehensive healthcare coverage Life insurance 401k with company match Work from home (or wherever) Creating a diverse and inclusive workplace is Bobtail’s nucleus. We are an equal opportunity employer and embrace people of different backgrounds, cultures, religions, national origins, races, colors, genders, gender expressions, sexual orientations, ages, marital status, veteran status, experiences, abilities and perspectives. Bobtail