Bobtail - Director of Product

Remote - United States (Remote)3w ago

Remote Director NA Fintech Payments Director of Product Founder Documentation Product Marketing Market Research Decision Making

Requirements

• 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.

Responsibilities

• 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. • Decide What to Build: • 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. • Process around decision making: • 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. • Decide What Not to Build: • 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. • Execute at a High Level: • 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. • Defend the Business Case: • 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 outcome: • 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. • Own the Product: • 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. • Obsess Over the Customer and the Product: • 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. • Evidence-Driven Decision Making: • Team Building: Hire and develop the product management function at Bobtail, defining process and hiring bar as the first dedicated product leader. • Team Building: • 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. • Market & Competitive Judgment: