[Hiring] Director of Product @Bobtail

Role Description

As Director of Product, your mission is to build the premier product organization in supply chain: disciplined about what you build, iterative in how you build it, obsessed with the customer, and driven by data at every decision.

We're hiring a Director of Product to lead product strategy, development, and innovation at Bobtail. This is a first-of-its-kind seat built around three priorities:

• Deciding what Bobtail builds
• Deciding what it deliberately does not build
• Executing at a high level in lockstep with engineering and the rest of the senior management team to ship it

You'll work directly with the CEO to turn a wide set of strategic options into a sequenced, evidence-backed roadmap.

The ideal candidate has:

• Led product at a company of comparable size and complexity
• A track record of setting strategy from ambiguity rather than just running an existing roadmap
• The discipline to say no as often as yes
• Strong product leadership skills to build the product management function at Bobtail from the ground up
• The ability to partner closely with engineering, design, and go-to-market leadership
• A focus on identifying new products, services, platform capabilities, and revenue opportunities
• An understanding of customer operations and pain points

Qualifications

• 8+ years of experience in product management and strategy
• Experience leading product at a company of comparable size and complexity
• 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
• Strong technical fluency
• Highly analytical and data-driven
• A bias toward shipping and iterating over long planning cycles
• Strong communication and cross-functional leadership skills
• Financial fluency
• An obsession with the customer and the product

Requirements

• Develop and maintain a product strategy that connects product investment to the company's broader strategic and financial objectives
• Create a disciplined process for gathering and evaluating ideas
• Establish clear criteria for when to build, continue investing, change direction, or discontinue an initiative
• Partner closely with engineering, design, go-to-market, and senior leadership
• Build and defend the revenue potential, development cost, and opportunity cost of each major roadmap bet
• Ensure new products have clearly understood operational, financial, regulatory, and risk requirements before launch
• Take full, unbounded ownership of Bobtail's product
• Establish a disciplined process for identifying and evaluating new product opportunities
• Build the muscle - data, customer research, experimentation - to validate bets before committing engineering resources
• Hire and develop the product management function at Bobtail
• Track how freight-tech and fintech infrastructure are evolving

Benefits

• Generous PTO
• Monthly Mental Break Day
• Parental leave
• Comprehensive healthcare coverage
• Life insurance
• 401k with company match
• Work from home (or wherever)