In this episode, Colin Nederkoorn, CEO and co-founder of Customer.io, takes us on a journey through his unconventional path from sales to becoming the leader of a globally recognized SaaS company. Colin shares how a quirky side project—booting Windows XP on Intel Macs—taught him to spot opportunities in tech and inspired his career pivot. He also reflects on building a successful remote-first company long before remote work became mainstream, the challenges of staying aligned as a distributed team, and the importance of connecting directly with customers.

We discuss how Colin and his co-founder identified a gap in the marketing automation space, their iterative approach to product development, and the deliberate choices they made to grow sustainably without relying heavily on VC funding. Colin provides insights into the challenges of scaling, the significance of picking the right market, and how he has evolved as a CEO over a decade of leading Customer.io.

Whether you're a startup founder, an aspiring CEO, or someone passionate about SaaS and entrepreneurship, this episode is packed with candid advice, inspiring stories, and practical lessons.

Key Topics Covered:

0:00 – Welcome & Introduction
Scott introduces Colin Nederkoorn his journey from quirky projects to leading Customer.io.

3:00 – Organizing the Windows XP on Mac Contest
Colin recalls a fun early career project that unexpectedly shaped his entrepreneurial mindset.

6:45 – From Shipping Sales to Tech
How working in sales for a petrochemical shipping company helped Colin build the foundation for his tech career.

10:00 – The Origin of Customer.io
Colin shares the real (non-Hollywood) story behind founding Customer.io and the problem they set out to solve.

15:30 – Scaling Without Venture Capital
Why Colin chose a more deliberate path to growth and how Customer.io thrived without heavy VC backing.

20:00 – Building a Fully Remote Company
Insights on running a distributed team since 2012, long before remote work became a trend.

25:30 – Staying Customer-Centric
The importance of staying connected to customers, even as the company scales.

30:00 – Rebranding for Growth
Colin discusses the decision to rebrand and how it aligned the product's capabilities with its market perception.

33:00 – Lessons in Leadership
How Colin’s leadership style has evolved over the years and the skills he believes are vital for any CEO.

35:00 – Advice for Aspiring Founders
Colin’s unconventional advice for founders: pick the right market and take a long-term approach to learning and growth.

Key Takeaways:

• Opportunities are everywhere: Colin’s career pivot began with an unusual tech contest, proving the value of curiosity and initiative.
• Remote work requires structure: Aligning a distributed team means formalizing communication and creating deliberate rituals.
• Choose your market wisely: A strong, growing market is the foundation for long-term success.
• Iterative growth beats pressure for fast wins: Colin’s journey shows that patience and sustainability often pay off more than rapid scaling.

Notable Quote:
"If you pick a good market, you can solve a lot of the other problems. But if you pick a small or tough market, those problems are near impossible to overcome."