Customer.io

Colin Neterkorn's journey to founding Customer.io began unconventionally. In his mid-20s, he rode his bike from San Francisco to Boston—4,000 miles in 57 days—as a transition period to figure out his next move. While riding, he applied for product management jobs expecting to land in San Francisco, but instead got an offer in New York. After relocating his belongings from San Francisco back to New York, he joined a product management role where he met his future co-founder. Together, they identified a clear market gap: companies needed intelligent, behavior-based email automation that didn't rely on sampling like analytics products of the era.

They were deliberate about their founding criteria. They wanted to build a SaaS business (recurring revenue), sell to peers (product managers and marketers), keep it connected to company revenue (so it wouldn't be cut during downturns), and make it technically challenging. Their original product vision was to email people based on what they did or didn't do in applications—a genuinely hard problem because you can't use sampling when sending precisely targeted messages. In April 2012, they launched with an ambitious but achievable goal: get five companies paying $10/month. Remarkably, one of those original five customers is still a customer today with $100K+ lifetime value.

From April 2012 to 2014, Customer.io scaled from those five $10/month customers to $1M ARR in approximately two years. The product remained fundamentally focused on the core value proposition—behavior-triggered messaging—but they added complementary features like transactional emails and newsletters that leveraged their segmentation engine. Colin emphasizes that this steady revenue growth masked numerous mistakes happening simultaneously.

The mistakes fell into three categories. First were infrastructure decisions that didn't improve the core product experience. They ran bare metal servers in a Quebec data center to save costs, partly to appeal to European customers worried about US data centers. When the fiber optic cable serving the bridge above the data center got cut, all servers became inaccessible—a crisis Colin hadn't anticipated needing to manage. Later, they chose an exotic closed-source distributed database that promised infinite scalability, but when that database company got acquired by Apple and stopped supporting their contract, the entire cluster fell over. Facing potential business shutdown with millions in ARR, Colin had to rebuild the entire backend using MySQL and traditional distributed databases. The lesson: customers don't care about elegant infrastructure; they care about reliability.

Technologically, betting early on a JavaScript MVC framework before version 1.0 proved costly. The framework changed dramatically between v0.x and v1.0, requiring a complete application rewrite. It also complicated hiring—new engineers either needed prior experience or extensive training. Most critically, customers didn't care about a responsive native-app-like interface; they wanted a CRUD app with powerful backend logic.

Organizationally, Colin made several people-related mistakes. He tried to run the business alone for too long, almost running out of money by late 2012 because he tried to raise capital during the November-December holiday period when investors are unavailable. This experience made him overly cautious about raising money, but it also meant the company was understaffed and burning out. He didn't formalize a board until 2017 (five years in), resisting the idea of having a boss after reading VC horror stories. He also didn't understand that his early sales calls with prospects—explaining the product and qualifying them—were actually sales, not just support. He hired "onboarding specialists" instead of real salespeople, delaying a proper go-to-market motion for years. Perhaps most painfully, he lost major customers like Shopify (their largest customer in 2013-14) when those customers hired new VPs of marketing who wanted different tools. There was no internal champion relationship. This eventually led to building a 35-person customer success team.

Customer.io grew from a bootstrapped startup of five $10/month customers to a company with 250+ employees and a mission-critical platform serving thousands of businesses. Colin credits several late-arriving changes: moving to cloud infrastructure (Google Cloud), hiring a Chief Revenue Officer to professionalize sales, building a dedicated customer success organization, creating a formal board, and joining a peer CEO network. By the time companies hit $10M ARR, Colin advises founders to clearly define what they want from the business—the option to sell and live off proceeds, or the commitment to build something much larger. For Customer.io and Colin, the answer was clear: the opportunity to build a massive outcome for the team and make a significant industry impact.