Director of Product

Bobtail; United States; A distancia; USD 180.000 - 260.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Generous PTO

Mental Break Day

Parental leave

Healthcare coverage

Life insurance

401k with company match

Work from home (or wherever)

Descripción de la vacante

Bobtail is seeking a Director of Product to lead product strategy, development, and innovation in the supply chain space. This pivotal role decides what to build, how to sequence it, and works with engineering and senior leadership to ship a clear roadmap.

The ideal candidate has led product at a company of similar size, turning ambiguity into strategy with data-driven judgment. You will build the product function, hire and mentor a team, and align with finance, design and GTM to deliver

Formación

• 8+ years of experience in product management and strategy at a comparable size and complexity.
• Track record of setting product strategy from ambiguity and defending sequencing with data and judgment.
• Experience in fintech, financial services, payments, lending, or other transaction-heavy environments preferred.
• Experience conducting product discovery, customer research, and market analysis; strong commercial instincts.
• 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.
• Strong technical fluency; ability to work with engineering on architecture and feasibility.
• Highly analytical and data-driven with strong problem-solving skills.
• Bias toward shipping and iterating over long planning cycles.
• Comfort operating at a founder-led, profitable company.
• Strong communication and cross-functional leadership; ability to influence senior stakeholders.
• Financial fluency; able to model revenue potential and costs; measure success by outcomes.
• Obsession with the customer and the product.

Responsabilidades

• Decide What to Build: Develop and maintain a product strategy aligned to company objectives.
• Process around decision making: Create a disciplined process for evaluating ideas and roadmaps.
• Decide What Not to Build: Establish clear criteria to continue, pivot, or discontinue initiatives.
• Execute at a High Level: Partner with engineering, design, GTM, and leadership to ship roadmaps on a predictable cadence.
• Defend the Business Case: Build and defend revenue potential, costs, and opportunity costs to finance stakeholders.
• Own the outcome: Ensure product requirements cover operational, financial, regulatory, and risk needs.
• Own the Product: Take full ownership of Bobtail's product across customer and platform touchpoints.
• Obsess Over the Customer and the Product: Talk directly with customers and understand competitors in transportation fintech.
• Evidence-Driven Decision Making: Use data, research, and experimentation to validate bets.

Conocimientos

Product management

Strategy leadership

Data-driven

Cross-functional leadership

Customer research

Financial acumen

Communication

Market analysis

Stakeholder management

Descripción del empleo

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.

About Bobtail

Bobtail is dedicated to increasing happiness by eliminating inefficiencies in the supply chain. We envision a supply chain without friction, fraud, waste, and abuse where companies succeed based on the value they create.

We work in a unique way at Bobtail, where we value teams over individuals and encourage experimentation and iteration to constantly improve. Teams are given flexibility in working towards a shared purpose and given the freedom to decide how they will accomplish their goals.

If you are an out of the box thinker that takes a proactive approach in collaborating with others to solve problems and achieve your goals - we would love to talk to you.

The things we value:

• Mission
• Teams over individuals
• Communication
• Iteration
• Experimentation and failing fast
• Initiative and solutions oriented approach
• Documentation
• Data
• Mental health and work life balance
• Diversity
• Transparency

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, and 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, with a track record of setting strategy from ambiguity rather than just running an existing roadmap, and the discipline to say no as often as yes. This individual will be highly data-driven and analytical, with the judgment to move on conviction when the data is inherently thin. We are looking for a strong product leader who can build the product management function at Bobtail from the ground up, hire and develop a team, and partner closely with engineering, design, and go-to-market leadership to turn decisions into shipped product. This includes identifying new products, services, platform capabilities, and revenue opportunities that solve meaningful problems for our customers and strengthen our competitive position. The right person will not wait for someone to hand them a list of features to build. They will spend time understanding how our customers operate, where they struggle, what they currently pay others to do, and what problems remain unsolved.

You should apply if you have:

• 8+ years of experience in product management and strategy, including experience leading product at a company of comparable size and complexity.
• A 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 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, including hiring the first few members of a function.
• Strong technical fluency - you don't need to write code, but you should be able 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.
• A 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, including the ability to clearly communicate product strategy and trade-offs to senior leadership. The discipline to say no - comfortable deferring or killing ideas that don't earn their place on the roadmap, even when they're compelling in isolation or popular internally. Demonstrated ability to influence across functions and challenge senior stakeholders constructively.
• Financial fluency - comfortable modeling and defending the revenue potential, development cost, and opportunity cost of a roadmap bet directly to the CFO and other finance stakeholders. A track record of measuring product success based on customer and business outcomes.
• An obsession with the customer and the product - you can't walk past something broken without wanting to fix it, and you know the product as well as the people using it, not just the roadmap slide.

You will be responsible for:

• Decide What to Build: Develop and maintain a product strategy that clearly connects product investment to the company's broader strategic and financial objectives. Look beyond incremental feature improvements to identify opportunities for meaningful product innovation.
• Process around decision making: Create a disciplined process for gathering and evaluating ideas without allowing the product roadmap to become a collection of stakeholder requests. Ensure completed functionality solves the underlying customer or business problem rather than simply meeting documented requirements.
• Decide What Not to Build: Exercise real judgment about scope. Establish clear criteria for when to build, continue investing in a new product, change direction, or discontinue an initiative.
• Execute at a High Level: Partner closely with engineering - and with design, go-to-market, and senior leadership - to turn the roadmap into shipped product on a predictable cadence, not just a plan.
• Defend the Business Case: Build and defend the revenue potential, development cost, and opportunity cost of each major roadmap bet to the CFO, so product decisions hold up under financial scrutiny, not just strategic conviction.
• Own the outcome: Ensure new products have clearly understood operational, financial, regulatory, and risk requirements before launch. Measure product success based on business outcomes - not simply whether features were delivered.
• Own the Product: Take full, unbounded ownership of Bobtail's product. There are no lanes here; if it touches the customer or the platform, it's yours to shape.
• Obsess Over the Customer and the Product: Establish a disciplined process for identifying and evaluating new product opportunities. Spend meaningful time talking directly with customers rather than relying exclusively on feedback filtered through Sales or Operations. Develop a strong understanding of competitors and adjacent providers within transportation finance and fintech. Live inside the carrier's day-to-day and inside the product itself. We want someone who can't walk past something broken without wanting to fix it, and who knows the product as well as the people using it.
• Evidence-Driven Decision Making: Build the muscle - data, customer research, experimentation - to validate bets before committing engineering resources, while being willing to move on conviction when the data is inherently thin.
• Team Building: Hire and develop the product management function at Bobtail, defining process and hiring bar as the first dedicated product leader.
• Market & Competitive Judgment: Track how freight-tech and fintech infrastructure are evolving, including AI-driven disruption and industry consolidation, and stress-test Bobtail's roadmap against it.
• Generous PTO
• Monthly Mental Break Day
• Parental leaveComprehensive healthcare coverage
• Life insurance
• 401k with company match
• Work from home (or wherever)

Creating a diverse and inclusive workplace is Bobtail’s nucleus. We are an equal opportunity employer and embrace people of different backgrounds, cultures, religions, national origins, races, colors, genders, gender expressions, sexual orientations, ages, marital status, veteran status, experiences, abilities and perspectives.