53: From eBay to Building AI Products (with Jennifer Deal)
Mon Feb 02 2026
For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested
THE GUEST
Jennifer Deal is a powerhouse AI product leader who’s been shaping the future of e-commerce, fintech, and martech for over a decade. From building billion-dollar marketplaces at eBay to unlocking more than $42 million in revenue through bold, data-driven innovation, she’s known for blending marketing intuition with deep product strategy and technical execution. Jennifer thrives at the intersection of customer obsession and enterprise transformation—turning insights into adoption and disruption into lasting loyalty. Today, she’s driving marketplace growth and seller success at Tmoo, while helping teams launch products customers can’t stop talking about. And in this episode, we’re diving into AI enablement for sellers and marketplaces.
THE SUMMARY
What you think you know about AI is basically irrelevant: Using AI casually creates false confidence. Real leverage comes from understanding how AI systems actually behave, where they break, and how they’re built. That mindset shift alone creates a massive competitive gap.
Engineering vocabulary is a career cheat code: You don’t need to code to win in AI, but you do need to speak the language. Knowing concepts like hallucinations, constraints, trade-offs, and system limits unlocks credibility with technical teams and positions non-technical leaders as real AI partners.
AI rewards people who think smaller, not bigger: The biggest mistake businesses make is trying to “AI-transform” everything at once. Starting with narrow, practical use cases creates faster ROI and avoids the complexity that stalls most AI initiatives.
Vibe coding turns ideas into products shockingly fast: Hands-on experimentation beats theory every time. Rapidly building scrappy tools — even personal ones — rewires how people think about product, execution, and feasibility in an AI-first world.
Planning cycles are collapsing because AI moves too fast: Annual plans became quarterly. Quarterly plans are becoming monthly. Falling in love with any solution is dangerous because the tech will obsolete it faster than teams expect.
AI levels the playing field — temporarily: Everyone is early. Even engineers are still catching up. The advantage belongs to those who get hands-on now, before AI fluency becomes table stakes instead of differentiation.
AI isn’t just a tool — it changes how everything gets built: From marketplaces to filmmaking to product development, AI collapses traditional stages of work. Everything starts happening at once, forcing leaders to rethink structure, sequencing, and decision-making.
THE SHOW
Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI.
THE LINKS
Have a question you want us to answer? Send it through to support@aicareerboost.com
Jennifer Deal
LinkedIn: https://www.linkedin.com/in/jenniferdeal
My links
LinkedIn: https://www.linkedin.com/in/pollymallen/
AI Career Boost: https://www.aicareerboost.com/
More
For more on building AI products and careers, along with early course announcement and special pricing, subscribe to the AI Career Boost mailing list at https://aicareerboost.com/interested THE GUEST Jennifer Deal is a powerhouse AI product leader who’s been shaping the future of e-commerce, fintech, and martech for over a decade. From building billion-dollar marketplaces at eBay to unlocking more than $42 million in revenue through bold, data-driven innovation, she’s known for blending marketing intuition with deep product strategy and technical execution. Jennifer thrives at the intersection of customer obsession and enterprise transformation—turning insights into adoption and disruption into lasting loyalty. Today, she’s driving marketplace growth and seller success at Tmoo, while helping teams launch products customers can’t stop talking about. And in this episode, we’re diving into AI enablement for sellers and marketplaces. THE SUMMARY What you think you know about AI is basically irrelevant: Using AI casually creates false confidence. Real leverage comes from understanding how AI systems actually behave, where they break, and how they’re built. That mindset shift alone creates a massive competitive gap. Engineering vocabulary is a career cheat code: You don’t need to code to win in AI, but you do need to speak the language. Knowing concepts like hallucinations, constraints, trade-offs, and system limits unlocks credibility with technical teams and positions non-technical leaders as real AI partners. AI rewards people who think smaller, not bigger: The biggest mistake businesses make is trying to “AI-transform” everything at once. Starting with narrow, practical use cases creates faster ROI and avoids the complexity that stalls most AI initiatives. Vibe coding turns ideas into products shockingly fast: Hands-on experimentation beats theory every time. Rapidly building scrappy tools — even personal ones — rewires how people think about product, execution, and feasibility in an AI-first world. Planning cycles are collapsing because AI moves too fast: Annual plans became quarterly. Quarterly plans are becoming monthly. Falling in love with any solution is dangerous because the tech will obsolete it faster than teams expect. AI levels the playing field — temporarily: Everyone is early. Even engineers are still catching up. The advantage belongs to those who get hands-on now, before AI fluency becomes table stakes instead of differentiation. AI isn’t just a tool — it changes how everything gets built: From marketplaces to filmmaking to product development, AI collapses traditional stages of work. Everything starts happening at once, forcing leaders to rethink structure, sequencing, and decision-making. THE SHOW Weekly conversations with the AI’s top product leaders. Join Polly Allen as she discovers the paths to success in the world of AI. THE LINKS Have a question you want us to answer? Send it through to support@aicareerboost.com Jennifer Deal LinkedIn: https://www.linkedin.com/in/jenniferdeal My links LinkedIn: https://www.linkedin.com/in/pollymallen/ AI Career Boost: https://www.aicareerboost.com/