Product Strategy Leader — Fintech & Logistics

Bobtail; United States; Remote; USD 180,000 - 260,000; Full time

Benefits offered by this job

Generous PTO

Mental Break Day

Parental leave

Healthcare coverage

Life insurance

401k with company match

Work from home (or wherever)

Job summary

Bobtail is seeking a Director of Product to lead product strategy, development, and innovation in the supply chain space. This pivotal role decides what to build, how to sequence it, and works with engineering and senior leadership to ship a clear roadmap.

The ideal candidate has led product at a company of similar size, turning ambiguity into strategy with data-driven judgment. You will build the product function, hire and mentor a team, and align with finance, design and GTM to deliver

Qualifications

• 8+ years of experience in product management and strategy at a comparable size and complexity.
• Track record of setting product strategy from ambiguity and defending sequencing with data and judgment.
• Experience in fintech, financial services, payments, lending, or other transaction-heavy environments preferred.
• Experience conducting product discovery, customer research, and market analysis; strong commercial instincts.
• 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.
• Strong technical fluency; ability to work with engineering on architecture and feasibility.
• Highly analytical and data-driven with strong problem-solving skills.
• Bias toward shipping and iterating over long planning cycles.
• Comfort operating at a founder-led, profitable company.
• Strong communication and cross-functional leadership; ability to influence senior stakeholders.
• Financial fluency; able to model revenue potential and costs; measure success by outcomes.
• Obsession with the customer and the product.

Responsibilities

• Decide What to Build: Develop and maintain a product strategy aligned to company objectives.
• Process around decision making: Create a disciplined process for evaluating ideas and roadmaps.
• Decide What Not to Build: Establish clear criteria to continue, pivot, or discontinue initiatives.
• Execute at a High Level: Partner with engineering, design, GTM, and leadership to ship roadmaps on a predictable cadence.
• Defend the Business Case: Build and defend revenue potential, costs, and opportunity costs to finance stakeholders.
• Own the outcome: Ensure product requirements cover operational, financial, regulatory, and risk needs.
• Own the Product: Take full ownership of Bobtail's product across customer and platform touchpoints.
• Obsess Over the Customer and the Product: Talk directly with customers and understand competitors in transportation fintech.
• Evidence-Driven Decision Making: Use data, research, and experimentation to validate bets.

Skills

Product management

Strategy leadership

Data-driven

Cross-functional leadership

Customer research

Financial acumen

Communication

Market analysis

Stakeholder management

Job description

Bobtail is seeking a Director of Product to lead product strategy, development, and innovation in the supply chain space. This pivotal role decides what to build, how to sequence it, and works with engineering and senior leadership to ship a clear roadmap.

The ideal candidate has led product at a company of similar size, turning ambiguity into strategy with data-driven judgment. You will build the product function, hire and mentor a team, and align with finance, design and GTM to deliver