Director of Product – Data-Driven, Customer-Obsessed

Bobtail, Inc.; Northern (KY); Hybrid; USD 180,000 - 280,000; Full time

Benefits offered by this job

Generous PTO

Monthly Mental Break Day

Parental leave

Comprehensive healthcare coverage

Life insurance

401k with company match

Work from home (or wherever)

Job summary

Bobtail, Inc. is seeking a Director of Product to lead product strategy, development, and innovation in supply chain.

This first-of-its-kind seat partners with the CEO to turn strategic options into a sequenced, evidence-backed roadmap, balancing customer needs with business goals. The ideal candidate has 8+ years in product leadership at scale, strong data skills, and the ability to hire and grow a product team while collaborating with engineering, design, and go-to-market.

Qualifications

• 8+ years of experience in product management and strategy at large, complex companies.
• Track record of setting strategy from ambiguity and defending sequencing with data and judgment.
• Experience in fintech or transaction-heavy environments highly preferred.
• Experience conducting product discovery, customer research, and market analysis.
• Strong commercial instincts and ability to evaluate opportunities by customer value and economics.
• Comfort with compliance and risk constraints (KYC/KYB, lending, payments) is a plus.
• Experience building and leading a product team, hiring first members.
• Strong technical fluency and ability to work with engineers on architecture.
• Highly analytical, data-driven, and able to move on conviction when data is thin.
• Excellent communication and cross-functional leadership; ability to say no when needed.

Responsibilities

• Decide What to Build: shape a strategy linking investment to company goals.
• Process around decision making: create a disciplined idea-gathering process for the roadmap.
• Decide What Not to Build: set criteria to prune scope and focus on impact.
• Execute at a High Level: partner with engineering and GTM to ship the roadmap.
• Defend the Business Case: justify revenue, cost, and risk to the CFO.
• Own the Product: take full ownership of Bobtail's product and platform.
• Own the Customer: talk directly with customers to uncover opportunities.
• Evidence-Driven Decision Making: use data, research, and experiments to validate bets.
• Team Building: hire and develop the product management function.
• Market & Competitive Judgment: monitor trends in freight-tech and fintech.

Skills

Product strategy

Data-driven decision making

Cross-functional leadership

Customer discovery

Market analysis

Financial fluency

Communication

Team leadership

Job description

Bobtail, Inc. is seeking a Director of Product to lead product strategy, development, and innovation in supply chain.

This first-of-its-kind seat partners with the CEO to turn strategic options into a sequenced, evidence-backed roadmap, balancing customer needs with business goals. The ideal candidate has 8+ years in product leadership at scale, strong data skills, and the ability to hire and grow a product team while collaborating with engineering, design, and go-to-market.