E44: Andrew Waitman on the Power of Generalists: Lessons from Scaling a $100M SaaS Company.

Why Listen: If you’re in growth mode and want to learn from a generalist who’s DONE it.Description: In this special two-hour conversation, Andrew Waitman—former CEO of Assent, Order of Ottawa inductee, and one of Canada’s most respected business leaders—reflects on his decade transforming a 25-person startup into a $100M ARR global SaaS powerhouse. Speaking candidly about his journey from engineer to venture capitalist to CEO, Andrew shares how being a generalist shaped his leadership, decision-making, and foresight in an era of rapid technological disruption. From balancing specialists with generalists, to navigating AI adoption, to building cohesive cultures that scale, Andrew offers hard-earned lessons on leadership, resilience, and the art of seeing patterns before others. This episode is both a masterclass in business growth and a deeply personal exploration of adaptability, humility, and the mindset required to thrive in uncertain times. Key Highlights:  Generalist mindset: How Andrew leveraged curiosity and adaptability across industries to become a successful leader and investor. Leadership as orchestration: Why CEOs act as conductors, aligning specialists into cohesive strategies that create lasting impact. Resilience and risk: Lessons on financing, decision-making, and managing trade-offs in fast-growing businesses. Foresight in disruption: How generalists anticipate trends in AI, regulation, and global markets before they become mainstream. Culture and cohesion: Why team cohesion is the “magic ingredient” that determines whether companies scale or stall. About Andrew:Andrew Waitman is the Executive Chairman and former CEO of Assent, where he transformed a 25-person startup into a global SaaS leader with more than $100M in annual recurring revenue and unicorn valuation. Recognized as 2024 CEO of the Year and inducted into the Order of Ottawa, Andrew is widely regarded as one of Canada’s most respected technology executives. His leadership at Assent not only drove exponential growth but also positioned the company as a trusted partner for organizations navigating complex supply chain sustainability and compliance challenges. Before Assent, Andrew served as CEO of Pythian, where he drove rapid international expansion and established the company as a leader in data and analytics services. He also held senior leadership roles at Celtic House Venture Partners and Entrust, contributing to IPOs, global growth strategies, and portfolio success stories. In addition, Andrew has served on multiple boards helping to shape Canada’s innovation economy. Across these roles, he has consistently demonstrated foresight, execution, and the ability to scale organizations through disruption while building strong, cohesive teams. Find Andrew Here LinkedIn:  https://www.linkedin.com/in/andrewwaitman/ Website:  https://www.assent.com/