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Core Competencies
Role fitCore Competencies
Use this summary to align your resume positioning with the role.
Demonstrates expertise in product strategy and management, with a strong focus on aligning product development with financial and strategic objectives. Proven ability to lead cross-functional teams, conduct market analysis, and leverage data to drive product success in fintech and transportation technology.
Highest-signal resume keywords
Product ManagementProduct Strategy DevelopmentCustomer ResearchFinancial FluencyCross-Functional Leadership
ATS Keywords
Tailor your resumeApplicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills
Product DiscoveryMarket AnalysisData-Driven Decision MakingTechnical FluencyRisk Management
Soft Skills
Strong CommunicationAnalytical Problem SolvingInfluencing Stakeholders
Industry Keywords
FintechFinancial ServicesTransportation TechnologyKYCPayments
About the role
Key responsibilities & impact- Lead product strategy, development, and innovation at Bobtail
- Decide what Bobtail builds and what it deliberately does not build
- Work directly with the CEO to turn strategic options into a sequenced, evidence-backed roadmap
- Develop and maintain product strategy connecting product investment to strategic and financial objectives
- Create a disciplined process for gathering and evaluating ideas
- Establish criteria for building, continuing, changing, or discontinuing initiatives
- Partner with engineering, design, go-to-market, and senior leadership to ship products on a predictable cadence
- Build and defend the revenue potential, development cost, and opportunity cost of roadmap bets to the CFO
- Ensure new products meet operational, financial, regulatory, and risk requirements before launch
- Measure product success based on business outcomes
- Own Bobtail's product across customer and platform experiences
- Conduct customer conversations, understand carrier operations, and analyze competitors and adjacent providers
- Use data, customer research, and experimentation to validate product bets
- Hire and develop Bobtail's product management function as the first dedicated product leader
- Track freight-tech and fintech infrastructure trends, including AI-driven disruption and industry consolidation
Requirements
What you’ll need- 8+ years of experience in product management and strategy, including experience leading product at a company of comparable size and complexity
- 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 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 and ability 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
- 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
- Ability to communicate product strategy and trade-offs to senior leadership
- Ability to influence across functions and challenge senior stakeholders constructively
- Financial fluency, including modeling and defending revenue potential, development cost, and opportunity cost
- Track record of measuring product success based on customer and business outcomes
- Strong customer and product orientation
Benefits
Comp & perks- Generous PTO
- Monthly Mental Break Day
- Parental leave
- Comprehensive healthcare coverage
- Life insurance
- 401k with company match
- Work from home (or wherever)