Jeremy Silva

Build Dynamic Products, and Stop the AI Sideshow — Eliza Cabrera (Workday) + Jeremy Silva (Freeplay)

Jul 23, 2025 · 18:10

Eliza Cabrera (Principal AI Product Manager at Workday) and Jeremy Silva (Product Lead at Freeplay) argue that companies must stop treating AI as a separate 'sideshow' and instead deeply integrate it into product strategy using a crawl-walk-run approach to build dynamic, differentiated experiences. They explain that bolt-on AI products result from centralized AI strategies quarantined from core product, leading to features like chatbots that demonstrate capability but don't solve real customer problems. Workday's example shows starting with Gen AI content generation and translations for knowledge bases (crawl), then a contextually aware assistant that processes PII (walk), and finally agentic capabilities that autonomously act on policy changes (run). The north star is AI products that feel like natural, cohesive parts of the experience, not bolt-on enhancements.

The Build-Operate Divide: Bridging Product Vision and AI Operational Reality

Jul 2, 2025 · 12:50

Jeremy Silva (Freeplay) and Chris Hernandez (Chime) argue that the biggest challenge in generative AI isn't building prototypes but crossing the 'quality chasm' from v1 to reliable v2 through operational iteration. They explain how the lower barrier to entry and faster iteration speed in Gen AI accentuate the need for high-quality ops, where product quality becomes a direct function of how fast teams move through monitoring, experimentation, and evaluation loops. Chris emphasizes that human-in-the-loop isn't just a safeguard but a feedback engine, and that existing QA and CX teams in operations are already equipped to become 'model shapers'—labeling data, testing prompts, and defining what good looks like. Jeremy introduces the emerging role of the 'AI quality lead,' a systems thinker who can run experiments and evaluations without writing production code. They conclude that scaling Gen AI is an operational and people challenge, not just a technical one, and that embedding quality and human feedback early is the key to building faster and better.