My Journey to Brightflag

Kevin Cohn
3 min readMay 13, 2019
Horseshoe Bend, Arizona; photo by the author

I’ve joined Brightflag as Chief Customer Officer. This is the short story of how I came to choose my next adventure.

When I stepped away from Smartling at the end of last year I had no preconceptions about what would come next. All I knew was that I wanted (to borrow a friend’s expression) to experience the luxury of time off, and for whatever was next to push me outside of my comfort zone.

This intentional lack of focus flummoxed more than a few founders, CEOs, investors, and recruiters, not to mention family and friends, most of whom assumed I knew exactly what I wanted to do and was playing coy. In fact, I seriously considered positions that would require relocation, have no customer-facing responsibility, or be with a services company, any one of which would be a significant change.

My willingness to cast such a wide net led to meetings with many amazing people that otherwise wouldn’t have taken place. I learned something from each of them and am deeply appreciative of their time. Ultimately, however, the process reinforced my strong affinity for what’s defined my career to date: customer-facing responsibility and software.

My friend and former colleague, Brian O’Reilly, introduced me to Ian Nolan and Alex Kelly, Brightflag’s co-founders, just after the new year. We had an introductory call, but I hadn’t even begun to unwind after an all-out sprint to the finish line at Smartling, and they were in the midst of raising their Series A funding. Almost two months passed before we met again, at which point our discussion progressed quickly.

Brightflag’s software is used by large corporations to transform legal service delivery. At its core is artificial intelligence that extracts insights from invoice narratives — the pages-long descriptions of how much is being charged for a piece of legal work, and why. These insights are used to make data-driven decisions at every step of the matter lifecycle, from resource selection to price negotiation to quality of service evaluation. They also drive automation of time-intensive processes like legal invoice review.

I’ve made no secret of my interest in the legal technology space, and the more I spoke with Ian and Alex, the more interested I became. Through my own research, I validated that legal departments are under intense pressure to modernize their operations, but are not being supported in doing so by the legacy enterprise legal management solutions.

We quickly settled on a scope of responsibility—marketing, sales, customer success, and partnerships—that would leverage my experience and expertise as well as push me outside of my comfort zone. From there we moved on to completing diligence and negotiating terms. Most people describe this part of the process as being filled with unexpected twists and turns. For me it was boring in the best way, a credit to Ian and Alex’s bias for action and focusing on what matters most. We signed the paperwork at 1:30 a.m.; seven hours later, I introduced myself at the company’s annual kick-off.

I’m grateful to Ian and Alex, and Brightflag’s board, for trusting me to help lead their company. I’m also grateful to Brian for introducing us, and to everyone else who supported me during this process, either as a sounding board, a reference, or both. Thank you.

The most successful startups are the ones that recruit and retain the best talent. To that end, I’m hiring for marketing, sales, and customer success positions in New York, Dublin, and Sydney. Contact me directly if you’re interested in learning more about how we’re transforming legal spend management.



Kevin Cohn

Chief Customer Officer at Brightflag. I write about issues relevant to and situations faced by SaaS companies as they scale.