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

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 Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.

In this episode of The Product Experience, hosts Lily Smith and Randy Silver speak with Damilola Adelekan, Lead Product Manager at Remedial Health, who discusses building pragmatic, people-centred solutions in Africa’s fragmented and under-resourced healthcare system.

Chapters
05:30 – Early Lessons from Volunteering and Nonprofits
07:00 – Why Digitising a Broken System Isn’t Enough
10:00 – Tackling Trust, Funding, and Fragmentation in Healthcare
12:30 – Collaborating Beyond the Organisation
14:30 – Building a Full Healthcare Supply Chain
16:00 – Pragmatism Over Perfection in Product Vision
18:00 – Cross-Team Collaboration at Scale
20:00 – Structuring Product Work Across Functions
22:00 – Communications Tips for Cross-Functional Leadership
24:00 – Increasing Tech Adoption Among Low-Digital-Literacy Users
26:00 – Customer Research in Low-Tech Contexts
28:00 – Voice of the Customer: Calls, Feedback, and Sales Teams
30:00 – What Inspires a Product Manager in Nigeria?

Featured Links: Follow Damilola on LinkedIn | Remedial Health | Inspire Africa | 'How I got my job in product' feature with Damilola at Mind The Product

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 Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.

In this episode of The Product Experience, Patrick Ndjientcheu, Chief Product and Technology Officer at Irembo, shares how his team transitioned from delivering projects for government to building a portfolio of scalable products.

Patrick talks about shifting mindsets from execution to strategy, spinning out payments and identity into independent products, and the challenges of balancing internal bias with customer needs.

He also reveals how Irembo is evolving into a super app, why sales enablement is crucial in a B2B context, and the lessons he has learned guiding teams through the move from project to product to product portfolio.

Six things we learned from Patrick

Project to product mindset: Repeat customer demand signals value, turn ad-hoc projects into structured products with identity, principles, and strategy.

Team restructuring without turnover: Shifting from project delivery to product development requires reorganising teams around capabilities.

Spinouts emerge from features: Payments and identity started as embedded features, but with scale and external demand, became standalone products.

Bias is real: Teams naturally over-index on the dominant revenue product. Separation, customer interviews, and rebranding are critical to balance focus.

Sales enablement matters: Without educating sales and customers on new platform capabilities, adoption stalls and value is under-communicated.

Leadership lesson: Product leaders must bring the whole organisation on the journey—marketing, sales, finance, and operations—not just product teams.

Featured Links: Follow Patrick on LinkedIn | Irembo | Inspire Africa

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 Product Manager’s Guide to Strategy in the Time of COVID-19. A recovering music journalist and editor, Randy also launched Amazon’s music stores in the US & UK.