Vice President, Product - AI / DTC

Job Title: VP of Product & Technology (Specialty Retail | DTC) Location: Remote (West Coast-leaning hours, U.S. or Canada)

About the Company A profitable, 50+ year specialty retail brand in the midst of a major growth phase — doubling number of stores while investing heavily in e-commerce, digital transformation, and AI. This is a lean, high-performing organization with a strong culture of ownership and a PE-backed mandate to modernize and scale. The company operates a hybrid retail + digital model with a loyal customer base and a differentiated experiential offering.

Responsibilities

• Own the full company technology and product roadmap — translating business strategy into a prioritized, multi-year plan with clear ROI accountability across all domains
• Serve as the Product Management Architect for the organization: building business cases, evaluating vendors, creating product briefs for engineering, and managing cross-functional alignment with business stakeholders
• Lead and unify Product, Engineering, QA, and IT teams (~30 FTEs + consultants) under a single strategic vision
• Drive AI transformation across the business — including workflow automation, operational efficiency, and cultural adoption of AI-first practices
• Own modernization initiatives including OMS replatform, cloud migration, loyalty program rollout, mobile presence, and technical debt reduction
• Partner with executive leadership to justify all technology investment and communicate technical decisions in business terms
• Serve as a player-coach — equally comfortable setting strategy and rolling up sleeves on key initiatives

Required Skills & Experience

• 12+ years of progressive product and technology leadership, with demonstrable experience as the most senior product voice in the organization
• Deep, hands‑on product management experience — has built and owned full-company roadmaps, not siloed product areas; must be able to step into a Director of PM role seamlessly if needed
• Has led both product and engineering teams; engineering leadership experience required, even if on an interim or matrixed basis
• Proven track record of driving AI transformation — workflow automation, efficiency gains, and headcount optimization through AI adoption
• Strong e-commerce and DTC background — understands inventory, omnichannel operations, and digital commerce at a meaningful scale
• Experience at smaller, high-growth, or PE-backed companies; end-to-end ownership mindset required
• Has led at least one major platform modernization effort (OMS, cloud migration, replatform, or equivalent)
• IC product management experience earlier in career strongly preferred

Compensation

• Base Salary: up to $250,000
• Total Compensation: ~$300,000 (includes performance-based incentives)

Additional Information

• Role is 100% remote; candidates must be based in the U.S. or Canada and available for West Coast-leaning business hours
• Must be authorized to work in the U.S. or Canada — no visa sponsorship available
• Title flexible based on experience (VP of Product & Technology, Head of Product & Technology, or Divisional CTO equivalent)
• Some travel required (1-2x per quarter)

For more information or to apply, contact Bethany at

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