Culture Through Chaos: Cherif Habib on Building Dialogue into a $290M Healthcare Giant

Welcome to the $100M Blueprint, your go-to podcast for real-world business lessons and entrepreneurial insights. Hosted by Goodfood founders Jonathan Ferrari and Neil Cuggy, it offers behind-the-scenes stories of scaling their company to $150M and beyond. Each episode features candid conversations with top entrepreneurs who’ve built $100M+ companies, delivering honest advice, leadership strategies, and hard-learned lessons for ambitious business owners. In this episode, hosts Jonathan Ferrari and Neil Cuggy sit down with Cherif Habib, co-founder and CEO of Dialogue, to explore the human-first strategies behind scaling a virtual healthcare company to a $290 million valuation. From IPO roadblocks to the now-famous “Mojo Memo,” Cherif shares hard-won lessons on leadership, culture preservation post-acquisition, and the art of balancing family with entrepreneurship. Whether it’s choosing instinct over consensus or staying loyal to your home market, this episode is packed with raw insights and practical advice for founders aiming to scale without losing sight of their mission or their people. Visit www.makegoodfood.ca to learn more about Goodfood, Canada's No.1 Meal Kit!

Welcome to the $100M Blueprint, your go-to podcast for real-world business lessons and entrepreneurial insights. Hosted by Goodfood founders Jonathan Ferrari and Neil Cuggy, it offers behind-the-scenes stories of scaling their company to $150M and beyond. Each episode features candid conversations with top entrepreneurs who’ve built $100M+ companies, delivering honest advice, leadership strategies, and hard-learned lessons for ambitious business owners.

In this episode, hosts Jonathan Ferrari and Neil Cuggy sit down with Cherif Habib, co-founder and CEO of Dialogue, to explore the human-first strategies behind scaling a virtual healthcare company to a $290 million valuation. From IPO roadblocks to the now-famous “Mojo Memo,” Cherif shares hard-won lessons on leadership, culture preservation post-acquisition, and the art of balancing family with entrepreneurship. Whether it’s choosing instinct over consensus or staying loyal to your home market, this episode is packed with raw insights and practical advice for founders aiming to scale without losing sight of their mission or their people.

What you will learn:

How to identify and capitalize on market gaps by focusing on B2B instead of B2C
The "Keep It Simple" principle for operational excellence during rapid growth
Why company values should evolve with your organization's growth stages
How to maintain culture through rapid scaling, IPO, and acquisition
The three-part framework for recovering lost "mojo"
How to structure angel investing activities without compromising your focus
The power of geographic focus in regulated industries like healthcare
Why defining reality while providing hope is the essence of effective leadership

Cherif Habib is the co-founder and CEO of Dialog, a pioneering virtual healthcare platform that has revolutionized access to medical services for organizations across Canada. With over nine years at the helm of Dialogue, he has grown the company from a startup to one valued at over $290 million, successfully leading it through both public and private phases. Under his leadership, Dialogue has transformed from an "Uber for healthcare" concept into Canada's leading B2B virtual health provider, serving major corporations while maintaining a steadfast focus on customer experience and corporate culture.

Visit www.makegoodfood.ca to learn more about Goodfood, Canada's No.1 Meal Kit!