VP of Product

Accountabilities:: As the VP of Product , you will own the product organization, roadmap, execution standards, customer feedback loop, competitive intelligence, and development of AI-native capabilities while serving as a strategic partner to executive leadership. Own product strategy and execution across storefronts, checkout, payments, merchant operations, and the AI agent. Define and manage the roadmap as a dynamic portfolio of prioritized opportunities, ensuring every major initiative has a clear business rationale, expected impact, and understood trade-offs. Establish a high standard for what constitutes a successfully shipped product, including adoption, measurable business impact, quality, usability, and sustained customer value. Provide detailed, hands-on feedback on product requirements, prototypes, specifications, launches, and other critical product work. Lead and develop a small team of principal-level Product Managers, setting expectations for quality, speed, ownership, and decision-making. Establish strong product management practices, including detailed PRDs, prototypes, specifications, test cases, launch plans, reference customers, and KPIs. Build direct relationships with key merchants, participating in regular customer conversations and developing deep knowledge of their businesses, funnels, needs, and pain points. Translate recurring merchant challenges into product improvements and ensure meaningful issues move rapidly from customer feedback to execution. Define and maintain competitive benchmarks across revenue per visitor, checkout conversion, page speed, approval rates, activation, retention, and user experience. Conduct hands-on competitive research by actively using competing products and monitoring changes in competitor offerings, pricing, and roadmaps. Ensure material competitive developments are analyzed promptly and translated into actionable response strategies. Lead the development of an AI-native product that merchants can confidently use for production-grade, revenue-impacting decisions. Personally test AI experiences, establish quality standards, define evaluation criteria, and ensure reliability across non-deterministic AI capabilities. Partner closely with the CTO and engineering leadership to align product and engineering execution. Ensure product specifications are established before delivery, timelines are visible, delivery risks are surfaced early, and engineering resources remain focused on high-value work. Eliminate or deprioritize initiatives that do not demonstrate sufficient customer or business value. Use experimentation, including appropriately sized A/B tests, to distinguish genuine product improvements from misleading or insufficient signals. Balance short-term execution with longer-term product strategy and contribute directly to strategic decisions about future product investments. Support product launches, rollout plans, customer education, incident reviews, and other operational aspects of product delivery. Maintain a high level of accountability for product outcomes, execution quality, and measurable customer impact. Requirements The role requires an experienced product leader with a strong builder mentality, technical fluency, commercial judgment, and a demonstrated ability to operate at both strategic and highly tactical levels in fast-moving environments. Experience as a #1 or #2 product leader at a growth-stage company. Demonstrated ownership of product areas where conversion, latency, reliability, or other product metrics had direct economic consequences. Proven ability to improve a product's competitive position against measurable performance or business metrics. Experience leading product strategy while remaining deeply involved in execution and product details. Strong technical fluency, including the ability to read pull requests, understand technical architecture, follow complex infrastructure or payment flows, and participate meaningfully in engineering discussions. Experience using modern AI tools for prototyping, product development, or workflow acceleration. Experience shipping AI-powered or LLM-based capabilities into production, with a practical understanding of evaluations, reliability, determinism, and non-deterministic systems. Experience building products for customers whose revenue depends directly on product performance. Background in fintech, payments, ecommerce, commerce technology, or another environment where conversion, reliability, speed, and availability have direct financial implications is highly valuable. Strong experience working directly with customers and translating customer feedback into product decisions. Demonstrated ability to lead, coach, recruit, and develop high-performing product talent. Strong product judgment and the ability to make decisive trade-offs in environments with limited resources. Excellent communication skills and the ability to provide clear, tactical, and constructive feedback to product and engineering teams. High ownership and entrepreneurial mindset, with a track record of solving problems independently and bringing actionable solutions rather than simply escalating issues. Ability to operate effectively under pressure while maintaining sound judgment and execution discipline. Experience working in fast-paced, resource-constrained startup environments within the past several years. Ability to balance immediate execution with long-term product strategy. Strong organizational skills and willingness to engage in operational details, including rollout plans, launch education, incident reviews, and requirements documentation. Experience with ecommerce, direct response, high-risk payments, checkout, subscription billing, or merchant-facing products is a significant plus. Experience operating a DTC or direct-response business personally is an additional advantage. Experience founding a company or serving as an early-stage operator with direct ownership of business outcomes is a plus. Ability to maintain exceptionally high standards while giving direct feedback, addressing performance issues early, and acknowledging mistakes openly. Benefits Remote work: Full-time remote position within the United States. Executive product ownership: Significant influence over product strategy, roadmap, execution standards, and future product investments. AI-native environment: Opportunity to build and scale AI-powered products designed to influence real commercial outcomes. Leadership opportunity: Lead and develop a team of senior, principal-level Product Managers. Executive partnership: Work closely with executive and engineering leadership on major strategic and product decisions. Customer proximity: Maintain direct relationships with key merchants and gain deep exposure to real-world commerce operations. High-impact environment: Work on a rapidly growing platform serving businesses where product performance directly affects revenue and growth. Cross-functional collaboration: Partner closely with engineering, analytics, operations, and other teams to turn product strategy into measurable outcomes. Startup environment: High ownership, fast decision-making, entrepreneurial execution, and substantial individual impact. Professional growth: Exposure to ecommerce, payments, AI agents, merchant operations, experimentation, and category-building product strategy.