Director of Product for Supply Chain Fintech at Bobtail

About Bobtail

Bobtail is a company committed to enhancing happiness by streamlining supply chain operations, aiming for a system free of friction, fraud, waste, and abuse where companies thrive based on their value creation. They foster a unique environment that prioritizes teams over individuals, encouraging constant improvement through experimentation and iteration. Teams are granted the autonomy to achieve shared objectives and define their working methods.

Bobtail seeks proactive, collaborative, and innovative thinkers who can effectively solve problems and achieve goals. The company values mission, teamwork, collaboration, communication, iteration, rapid experimentation, initiative, solution-oriented approaches, documentation, data, mental health, work-life balance, diversity, and transparency.

The Opportunity

Bobtail is hiring a Director of Product to spearhead product strategy, development, and innovation. This pivotal role focuses on three key areas: determining what Bobtail builds, deciding what it intentionally does not build, and ensuring high-level execution in close partnership with engineering and senior management to ship products. You will collaborate directly with the CEO to transform a broad range of strategic options into a structured, evidence-backed product roadmap.

The ideal candidate will have prior experience leading product development at a company of similar scale and complexity, demonstrating a history of defining strategy from ambiguous situations rather than simply managing existing roadmaps. This role requires the discipline to decline ideas as often as accepting them, a highly data-driven and analytical approach, and the judgment to act on conviction when data is limited. We are looking for a strong product leader capable of establishing the product management function at Bobtail from the ground up, hiring and developing a team, and working closely with engineering, design, and go-to-market leadership to translate decisions into shipped products. This includes identifying new products, services, platform capabilities, and revenue opportunities that address customer needs and bolster competitive standing. The successful candidate will proactively identify customer problems and solutions, rather than waiting for a predefined feature list.

Qualifications

• 8+ years of experience in product management and strategy, including leadership roles at companies of comparable size and complexity.
• A proven track record of developing product strategy from ambiguity and supporting sequencing decisions with both data and sound judgment.
• Strong preference for experience in fintech, financial services, payments, lending, factoring, transportation technology, or other transaction-heavy financial environments.
• Experience conducting product discovery, customer research, and market analysis.
• Strong commercial acumen and the ability to evaluate product opportunities based on customer value and business economics.
• Comfort with compliance and risk constraints (e.g., KYC/KYB, lending, payments) is a plus.
• Experience building and leading a product team, including the initial hiring phase for a new function.
• Strong technical fluency; while coding is not required, the ability to collaborate closely with engineering on architecture trade-offs and technical feasibility is essential.
• Highly analytical and data-driven, with strong pattern recognition and problem-solving skills.
• A bias toward shipping products and iterating quickly over lengthy planning cycles.
• Comfort operating within a founder-led, profitable company rather than a venture-subsidized environment.
• Strong communication and cross-functional leadership skills, including the ability to clearly articulate product strategy and trade-offs to senior leadership.
• The discipline to say no, comfortable deferring or discontinuing ideas that do not earn their place on the roadmap, even if they are compelling in isolation or popular internally.
• Demonstrated ability to influence across functions and constructively challenge senior stakeholders.
• 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, meaning you proactively address issues and possess deep knowledge of both the product and its users, beyond just roadmap slides.

Responsibilities

• Decide What to Build: Develop and maintain a product strategy that explicitly links product investment to the company's broader strategic and financial goals. Identify opportunities for significant product innovation beyond incremental feature improvements.
• Process Around Decision Making: Implement a disciplined process for gathering and evaluating ideas, preventing the product roadmap from becoming merely a collection of stakeholder requests. Ensure completed functionality genuinely solves the underlying customer or business problem, rather than just meeting documented requirements.
• Decide What Not to Build: Exercise careful judgment regarding scope. Establish clear criteria for when to build, continue investing in, change direction, or discontinue an initiative.
• Execute at a High Level: Partner closely with engineering, design, go-to-market, and senior leadership to reliably translate the roadmap into shipped products on a predictable cadence.
• Defend the Business Case: Construct and defend the revenue potential, development cost, and opportunity cost of each major roadmap investment to the CFO, ensuring product decisions withstand financial scrutiny in addition to strategic conviction.
• Own the Outcome: Ensure new products have clearly understood operational, financial, regulatory, and risk requirements prior to launch. Measure product success based on business outcomes, not merely feature delivery.
• Own the Product: Take comprehensive, unbounded ownership of Bobtail's product. This means shaping anything that impacts the customer or the platform.
• Obsess Over the Customer and the Product: Establish a disciplined process for identifying and evaluating new product opportunities. Spend significant time interacting directly with customers, avoiding sole reliance on feedback filtered through Sales or Operations. Develop a deep understanding of competitors and related providers in transportation finance and fintech. Live and breathe the carrier's daily experience and the product itself, driven to fix anything that is broken and knowing the product as well as its users.
• Evidence-Driven Decision Making: Build the capabilities (data, customer research, experimentation) to validate bets before committing engineering resources, while also being prepared to act on conviction when data is inherently scarce.
• Team Building: Hire and develop the product management function at Bobtail, defining processes and hiring standards as the first dedicated product leader.
• Market & Competitive Judgment: Monitor the evolution of freight-tech and fintech infrastructure, including AI-driven disruption and industry consolidation, and stress-test Bobtail's roadmap against these trends.

Benefits

• Generous Paid Time Off (PTO)
• Monthly Mental Break Day
• Paid Parental Leave
• Comprehensive Health Insurance coverage
• Life Insurance
• 401(k) with Company Match
• Work from home (or wherever)

Bobtail is dedicated to creating a diverse and inclusive workplace. They are an equal opportunity employer and welcome individuals of all backgrounds, cultures, religions, national origins, races, colors, genders, gender expressions, sexual orientations, ages, marital statuses, veteran statuses, experiences, abilities, and perspectives.