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AI Product Strategist
Benjamin Scott
Full-time · Mid-level · Chicago
About the role
Two years ago we launched an AI feature that no one used. Not because the model was bad — the model was actually quite good. It was because we shipped something technically impressive that solved a problem our users didn't have. That failure changed how we think about product strategy entirely. We now run discovery sessions every month, validate assumptions with data before committing to a roadmap, and obsess over the gap between what users say they want and what they actually do. We're hiring an AI Product Strategist to be the person who holds that thread — who can sit in a customer call, understand the pain, translate it into a product hypothesis, sanity-check it against what's technically feasible, and turn it into a prioritised roadmap item with a clear success metric. You don't need to have a CS degree. You do need to have a track record of making good product bets with imperfect information.
Responsibilities
- Lead quarterly discovery cycles to identify the highest-value AI opportunities
- Write product strategy documents that connect user pain to business value to technical feasibility
- Define success metrics for AI features before development begins
- Collaborate with engineering and ML teams on tradeoff decisions and scope
- Present strategy and roadmap to leadership and major customers
Requirements
- 4–6 years in product strategy or senior product management, with AI products specifically
- Able to interpret data independently — SQL queries, funnel analysis, statistical significance
- Comfort with Python for light data analysis and working with technical documentation
- Experience evaluating AI feasibility — you know what questions to ask the ML team
- Familiarity with LLM capabilities and limitations in a product context (via OpenAI API or equivalent)
- Exceptional written communicator — strategy memos, PRDs, and executive presentations
Benefits
- Strategic ownership across an AI-first product suite
- Full remote with quarterly in-person strategy sessions
- $95,000 – $120,000 base salary + equity
- Conference and networking budget: $2,500 annually
- Direct access to founder and executive team
Job Type
Full-time
Level
Mid-level
Language
English
Salary Range
$95,000 – $120,000
AI Expertise
AI Product & Strategy
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