Director of Product

🕒 September 22

🦀 Maryland – Remote

🦀 Maryland – Remote

⏰ Full Time

🔴 Lead

✅ Product Manager

👻 Ghost score 24%

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Bobtail

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2015

📦 Logistics

💼 Consulting

✈️ Travel

💰 $61.5M Debt Financing on 2022-03

Logistics • Consulting • Travel

Bobtail is a company offering financial solutions and tools tailored for the trucking industry. Their services include the Bobtail Fleet Card, which provides significant fuel savings, and factoring services that offer same-day funding without long-term commitments. Additionally, Bobtail provides resources and support to help trucking businesses manage their operations efficiently. The company also engages with the trucking community through a podcast and a blog, offering business tips and insights.

📋 Description

• 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

• 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

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

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