Director of Product

Our client is seeking a Director of Product to own the end-to-end product experience at a fast-growing technology company operating at the intersection of fintech, HR technology, and AI
. This is a player-coach role reporting directly to the CEO. You will shape product strategy alongside senior leadership, lead and grow a combined product and design organization, and remain hands-on enough to prototype, provide thoughtful critique, and help drive products from concept through launch.

What You’ll Do

• Own the product vision and roadmap across a suite of workforce, payroll, benefits, and financial products, ensuring they come together as a seamless experience
• Establish a high bar for product quality and design, ensuring every interaction, workflow, and piece of content reflects strong product judgment
• Define how users interact with AI-powered and agentic software
  , creating experiences that feel intuitive, transparent, trustworthy, and genuinely useful
• Embrace AI-native product development by rapidly prototyping concepts, testing with customers, incorporating feedback, and accelerating the path from idea to launch
• Lead, hire, mentor, and develop a high-performing product and design organization, fostering strong collaboration between product, design, and engineering
• Build strong customer feedback loops across both growing businesses and larger enterprise organizations, translating customer needs into meaningful product improvements
• Partner closely with engineering on prioritization, technical tradeoffs, product quality, and execution
• Balance product delight with accuracy and reliability, particularly across complex workflows involving compliance, taxation, financial transactions, and other high-stakes requirements
• Help shape the broader company narrative, with product strategy and execution contributing to sales, fundraising, customer conversations, and market positioning

What We’re Looking For

• 5+ years of product management experience
  , including 2+ years leading product teams
  , with a track record of shipping complex B2B, fintech, SaaS, or similarly sophisticated products
• Strong product and design fluency—you can challenge a product requirements document while also providing meaningful feedback on user experience and visual design
• Exceptional product taste and a demonstrated ability to create experiences that stand out, even within traditionally complex or unglamorous categories
• An AI-native mindset with hands-on experience using modern AI tools to prototype, build, test, or improve products
• Strong perspective on how to make LLM-powered and agentic experiences intuitive, reliable, transparent, and valuable rather than gimmicky
• Experience in fintech, payroll, HR technology, payments, financial services, or another regulated/correctness-critical industry is highly desirable
• Comfortable operating in ambiguous, fast-moving environments with significant ownership and accountability
• Excellent communication skills and the ability to work effectively with executives, founders, customers, engineers, and other stakeholders
• A proven ability to identify, hire, mentor, and develop high-caliber product and design talent

Nice to Have

• Early-stage or founding product/design experience
• Experience building global products, including localization, multi-country compliance, or cross-border financial workflows
• Experience serving both SMB and enterprise customer segments
• Experience scaling products through periods of rapid growth and organizational change

Why Join

Join a high-growth technology company building the next generation of AI-powered workforce and financial solutions
. You’ll have significant ownership over the product vision and the opportunity to shape how businesses manage complex workforce and financial operations through a modern, intelligent software experience.