Why He Tackles 'Unsolvable' Problems

In this episode of The Product Experience, Lily Smith speaks with Sahil Jain, co-founder and CEO of Samepage.ai, about one of product management’s hardest challenges: keeping teams aligned. 

From his early career at Yahoo and AOL to founding multiple startups, Sahil shares lessons on building products that tackle “unsolvable” problems like communication and alignment. He explains why shared understanding matters more than speed, how product managers can become better storytellers, and why early-stage startups should obsess over just a handful of teams before chasing scale.

Chapters

• 0:00 – Why alignment is so hard
• 1:14 – Sahil’s unconventional career path
• 4:00 – First foray into startups at AOL and beyond
• 6:50 – Founding AdStage and lessons from raising early capital
• 9:00 – Moving into product leadership after acquisition
• 12:53 – On delusion, motivation, and tackling “unsolvable” problems
• 16:34 – Starting Samepage.ai and the problem of information asymmetry
• 22:43 – Validating the problem and testing prototypes
• 27:22 – Why product managers are the perfect early adopters
• 29:20 – The first 10 obsessed teams: startup focus
• 34:00 – Neurodivergence, communication, and shared understanding
• 36:43 – From Claude Shannon to storytelling: frameworks for better communication
• 39:59 – Lessons from Duolingo on multimodal learning
• 41:19 – Where to find Samepage.ai

Featured Links: Follow Sahil on LinkedIn | Samepage.ai | 'What we learned at Industry conference - day one' feature by Louron Pratt at Mind the Product

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Our Hosts
Lily Smith enjoys working as a consultant product manager with early-stage and growing startups and as a mentor to other product managers. She’s currently Chief Product Officer at BBC Maestro, and has spent 13 years in the tech industry working with startups in the SaaS and mobile space. She’s worked on a diverse range of products – leading the product teams through discovery, prototyping, testing and delivery. Lily also founded ProductTank Bristol and runs ProductCamp in Bristol and Bath.

Randy Silver is a Leadership & Product Coach and Consultant. He gets teams unstuck, helping you to supercharge your results. Randy's held interim CPO and Leadership roles at scale-ups and SMEs, advised start-ups, and been Head of Product at HSBC and Sainsbury’s. He participated in Silicon Valley Product Group’s Coaching the Coaches forum, and speaks frequently at conferences and events. You can join one of communities he runs for CPOs (CPO Circles), Product Managers (Product In the {A}ether) and Product Coaches. He’s the author of What Do We Do Now? A...