
Deployed: The AI Product Podcast
Deployed is the podcast for people building AI products.With all the hype about AI over the past two years, it’s often been hard to discern what’s actually working. We started Deployed to share the real-world stories of the leaders, engineers, product & design teams, and data teams who are building and running great generative AI products for their customers. In each episode we’ll dig into the journey to create these products, the impact they’re making for customers and the bottom line, and what it takes to make generative AI products successful. Our hope is to add a bit of signal in all the noise, and help you stay ahead of the curve when it comes to strategies and tactics that actually work in production.We’d love to hear from you, please reach out to us at team@freeplay.ai.You can also learn more about what we’re building at Freeplay here: freeplay.ai
Latest episodes

Apr 25, 2025 • 38min
Insights from the Cutting Edge of AI Investing: A Conversation with Sarah Guo, Founder of Conviction
On this episode we talk with Sarah Guo, founder of Conviction — a VC firm focused on early-stage AI investments. Sarah shares insights from her unique position at the intersection of AI research, startups, and enterprise adoption that are relevant to people building with AI. Topics like: How successful teams keep up with rapid changes in the AI landscape, how AI labs vs. enterprises approach problems differently, thoughts on why many AI initiatives struggle to move from prototype to production. She also shares some good advice for leaders on setting an ambitious roadmap and staying competitive in the current market. This conversation provides practical perspective on what's working with leading AI teams, and hopefully some advice others can learn from.

Mar 27, 2025 • 43min
The Secrets To Being A Great AI PM: Evals, Quality & More | Apollo.io AI Product Lead, Tyler Phillips
On this episode we talk with Tyler Phillips, AI Product Lead at Apollo.io, about what it really takes to build successful AI products in sales. Tyler shares surprisingly candid insights about the "unsexy" but critical work that great AI PMs do - from spending hours evaluating AI outputs to building systematic quality frameworks. Learn why it can help for domain experts should write prompts instead of engineers, how Apollo measures AI quality across their products, and the practical strategies they've developed after some early missteps. Whether you're an aspiring AI PM or an engineering leader trying to structure your team effectively, this conversation offers useful lessons on what actually drives AI product success.

Feb 20, 2025 • 44min
Building Box's AI Platform: Enterprise Lessons in Scaling LLMs | Ben Kus, CTO of Box
On this episode of Deployed: The AI Product Podcast, we sit down with Ben Kus, CTO of Box, to unpack how they built a secure, scalable AI platform within their enterprise content management system. Ben shares candid insights from Box's journey integrating AI capabilities while maintaining enterprise-grade security for sensitive customer data. Learn practical strategies for evaluating AI quality without accessing customer data, building internal platforms that engineering teams want to use, and designing architecture that can evolve with rapid AI advances. Whether you're integrating LLMs into an established product or building new AI features, this conversation offers valuable lessons on balancing innovation with enterprise requirements. Join Ian, Co-Founder and CEO of Freeplay, for this in-depth discussion on scaling AI responsibly in the enterprise.

Jan 23, 2025 • 43min
Building Enterprise-Grade AI Agents: Lessons from Sierra's Arya Asemanfar
In this discussion with Arya Asemanfar, a Product and Engineering leader at Sierra, listeners discover how AI-powered agents are revolutionizing customer interactions. Arya explains the critical differences between traditional chatbots and advanced agents that take meaningful actions. The conversation dives into Sierra's innovative 'Agent OS' that ensures robust, scalable development and addresses challenges like tool hallucination. Arya highlights the importance of collaboration with customers, showing how tailored solutions enhance customer service while reflecting brand values.

14 snips
Jan 6, 2025 • 52min
How Help Scout Moved From Traditional SaaS To An AI-Native Product Company: A Conversation with Nick Francis & Luis Morales of Help Scout
Nick Francis, CEO of Help Scout, and Luis Morales, VP of Engineering, dive into their journey transforming a 13-year-old customer support platform into an AI-first company. They discuss their shift from skepticism to embracing AI for enhancing customer experiences. The duo shares insights on experimenting with AI features, evolving business models, and the challenges of prompt engineering. They emphasize the importance of an experimentation-driven culture and the new role of AI product quality experts, offering valuable advice for companies navigating AI integration.

26 snips
Dec 10, 2024 • 53min
Insights from Building AI Systems At Google Scale: In Conversation With Kyle Nesbit
Kyle Nesbit, a longtime Googler with 17 years of experience in AI and distributed systems, shares invaluable insights about building AI at scale. He discusses the challenges of transitioning traditional engineering teams to embrace LLM development and underscores the importance of starting with solid evaluation metrics. Kyle reveals strategies for iterative improvement, tackling data discovery issues, and balancing product quality during scaling. He also provides a peek into the real story behind AI demos and the complexities of integration within organizations.

Nov 25, 2024 • 48min
Creating an AI-Powered News App with Particle Co-Founder Sara Beykpour
Sara Beykpour, Co-founder and CEO of Particle, discusses how her news app uses AI to revolutionize news consumption. She highlights the challenges of summarization and the importance of maintaining quality and trust in AI-generated content. Sara shares insights on prompt engineering and integrating user feedback into product development. The conversation also touches on evolving attitudes towards AI in journalism and how tech firms can collaborate with publishers to enhance reliability in news. A must-listen for anyone curious about AI's role in media!

Nov 15, 2024 • 53min
Building Enterprise-Grade AI at Scale: Inside Workday's Journey with Generative AI
Eliza Cabrera, Principal Product Manager at Workday, and Beau Lyddon, Principal Engineer, share their insights on implementing generative AI at scale. They discuss the journey of integrating AI into enterprise products, emphasizing user adoption and effective collaboration. Key topics include selecting initial use cases, prompt engineering, and maintaining data privacy. Eliza and Beau highlight the balance between innovation and reliability, offering practical lessons for teams navigating the complexities of AI in a corporate environment.

Sep 24, 2024 • 49min
Build the Right Product Faster With The Help of AI: Lessons Learned from Maze Co-Founders Jo Widawski & Thomas Mary

4 snips
Sep 17, 2024 • 38min
Building High-Performance AI Engineering Teams with Mike Conover, Co-founder & CEO of Brightwave
Mike Conover, co-founder and CEO of Brightwave, dives into the challenges and capabilities of AI in financial research. He discusses limitations of large language models (LLMs) and the importance of effective information retrieval. Mike shares insights on building strong AI engineering teams and the significance of practical collaboration between analysts and engineers. He emphasizes the need for customized AI solutions to enhance product outcomes, illustrating how Brightwave revolutionizes market analysis.
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