Director of Product

This is a fully remote position, open to applicants in Maryland.

📋 Description

• Lead the strategy, development, and innovation of products at Bobtail.

• Determine what Bobtail should develop and what it will intentionally not pursue.

• Collaborate directly with the CEO to transform strategic options into a sequenced, evidence-based roadmap.

• Formulate and uphold a product strategy that aligns product investments with strategic and financial goals.

• Establish a structured process for collecting and assessing ideas.

• Set criteria for initiating, continuing, modifying, or terminating initiatives.

• Collaborate with engineering, design, go-to-market teams, and senior leadership to deliver products consistently.

• Construct and justify the revenue potential, development costs, and opportunity costs associated with roadmap decisions to the CFO.

• Ensure that new products comply with operational, financial, regulatory, and risk standards before their launch.

• Evaluate product success based on business outcomes.

• Oversee Bobtail's product offerings across customer and platform experiences.

• Engage in conversations with customers, comprehend carrier operations, and analyze competitors and related providers.

• Leverage data, customer insights, and experimentation to validate product strategies.

• Recruit and nurture Bobtail's product management team as the initial dedicated product leader.

• Monitor trends in freight-tech and fintech infrastructure, including AI-driven disruptions and industry consolidations.

⛳️ Requirements

• Over 8 years of experience in product management and strategy, with a history of leading product efforts at a similarly sized and complex organization.

• Proven ability to establish product strategy amidst uncertainty and support sequencing decisions with data and sound judgment.

• Preferred experience in fintech, financial services, payments, lending, factoring, transportation technology, or another transaction-intensive financial sector.

• Proficient in conducting product discovery, customer research, and market analysis.

• Strong commercial instincts with the capability to assess product opportunities based on customer value and business economics.

• Familiarity with compliance and risk constraints (KYC/KYB, lending, payments) is advantageous.

• Experience in building and leading a product team, including the recruitment of initial team members.

• Strong technical understanding and the ability to collaborate closely with engineering on architectural trade-offs and technical feasibility.

• Highly analytical and data-oriented, with exceptional pattern-recognition and problem-solving abilities.

• Preference for shipping and iterating rather than engaging in lengthy planning cycles.

• Comfort in operating within a founder-led, profitable organization as opposed to one reliant on venture funding.

• Excellent communication and cross-functional leadership capabilities.

• Ability to articulate product strategy and trade-offs to senior leadership effectively.

• Capacity to influence across various functions and constructively challenge senior stakeholders.

• Financial fluency, including the ability to model and justify revenue potential, development costs, and opportunity costs.

• Proven track record of measuring product success based on customer and business outcomes.

• Strong focus on customer needs and product orientation.

🏝️ Benefits

• Generous paid time off (PTO).

• Monthly Mental Break Day.

• Parental leave.

• Comprehensive healthcare coverage.

• Life insurance.

• 401k with company matching.

• Flexibility to work from home (or any location).