What obsessing over communication taught me - Sahil Jain (Co-Founder and CEO, Samepage.ai)

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Oct 1, 2025

Sahil Jain, the co-founder and CEO of Samepage.ai, shares his journey from Yahoo and AOL to founding startups. He dives into the challenge of information asymmetry in teams and emphasizes that alignment is more essential than speed. Sahil discusses the importance of storytelling in product management and the need for a focused approach on a few teams before scaling. He also tackles the role of neurodivergence in communication and how effective messages can be tailored to different audiences for better understanding.

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ANECDOTE

From Tester To Founder

Sahil started working at Yahoo as a 17-year-old tester and taught himself to code to automate tests.
That early hands-on experience pulled him into tech and set the stage for entrepreneurship.

ANECDOTE

What A Million Dollars Bought

Sahil raised $1M at age 21 and quickly launched AdStage with a co-founder and CTO.
He ran the company through eight years of growth, raising $17M and eventually selling it in 2020.

INSIGHT

Why Meetings Still Start With Catch‑Ups

Information asymmetry causes recurring meeting catch-ups despite many communication tools.
The core problem is not channels but creating shared understanding across people.

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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...