Scott McGillivray

A big thing for me is transitioning from the loose, everybody-wears-every-hat model of a startup into a business with long-term viability and a strategy for scaling up while building the discipline that creates predictable value. My realm is technology, and this approach is valuable to startups aiming at verticals like finance, health care, or other highly-regulated industries. Whether you have a disruptive business model or technology, it’s important to appeal to the incumbent players and pass muster with regulators. Aside from those factors, I try to approach clients from the perspective of a CIO. This is the way we work together to make sure the whole team is leveraging their technology to build value and stay secure. It’s not always glamorous, but this work is reflected in spending, headcount, risk modeling, and ultimately profitability. Once a company’s senior leadership tells their team, “We want you to be great at your work, and you’ll be rewarded for it; and here are the boundaries we need to work within,” it helps set expectations and build a predictable operating model.

A win that makes me happy is when I served as the CTO for a VERY early-stage SaaS startup. When I met them, they had a pretty good proof-of-concept demo and had sold it to a handful of prospective customers in their target market. They brought me in to deliver the product before a contractual deadline: 6 months later, or they would have to give the money back. I was responsible for defining the application and infrastructure architecture, and bringing in the necessary engineering and UX talent to get it done. 5 months later, we had an MVP to show to the paid customers and other prospects. At the 6-month mark, we had the early customers in production on our platform. Going from zero to production so quickly was an amazing journey, and I’m glad I had fantastic people on my team. I was deeply involved in the whole process, working with requirements, coaching the team, meeting with customers, scheduling deliverables, and I wrote all the documentation myself. That was an incredible ride, and I’d love to do it again.