Just about four months ago, I got in my car for what would be my last afternoon commute from Constant Contact – a company I called home for an incredible ten years. Over those ten years, in all the various positions I held at Constant Contact, I had the opportunity to help tens of thousands of small business owners – each and every one an entrepreneur – follow their dreams and make a go at building sustainable businesses by bringing real value to their customers. I look back at my time at Constant Contact and feel nothing but pride with how we never faltered from our values, mission, and culture of helping small business owners succeed in achieving real customer engagement with real business results. As I drove home in that final rush hour traffic, I had no definite plans as to where I would ‘land next’ nor did I know what form my next career challenge would take; however, I did know one thing, I was going to take some time to step back and carefully look for a challenge that would allow me to again tap into that passion for helping entrepreneurs reach their goals and dreams.
Four Months Of (Re) Connecting
Over the past four months, in addition to having time to reconnect with my wife and three young-ish boys, I have used this time to connect (or reconnect) with dozens of founders of very early and mid-stage companies, principals of venture and private equity firms, and CEO’s of scaled / growing companies – all mainly in the Boston area. My goal was to educate myself about what was going on in our region, to understand the trends and challenges facing these companies, and to determine where and how I ultimately saw myself contributing when I was ready to come back to a full time position. During this process, I had the opportunity to spend quality time with Michael, John, and the entirety of the Underscore team who, at that time, were assembling a new type of firm based on the idea of doing something new and different in the venture world. They all consistently explained to me that they were (and are) on a mission to find a better way to empower entrepreneurs and to support the entrepreneur’s full potential by involving other current, relevant subject and functional experts from the Boston area. Wait a minute, I thought, this seems very similar to the mission driven reality I had just had at Constant Contact which was so important to me and so I was very intrigued.
This all sounded so great in theory; however, I wanted to see it in action so Michael and team introduced me to people like David Hurley, the founder of their first portfolio company, Mautic, and other company founders with whom Michael and team were working. David spoke about the Core community as an extension of Mautic and an already aligned, valued, and trusted source of inspiration and practical advice. This idea that Michael discussed was in action and already contributing to the success of Mautic and other portfolio companies. This idea was real. It was more than just a theory or aspiration. This idea might just be the thing that would allow me to continue to tap into my passion. After these meetings, I had some vacations planned which allowed me some time to think and formulate my thoughts. Did I want to be involved? Could I help and contribute to its success? During that time I heard from Michael and the team that they had some ideas as to how we could help each other out. This was good because my thoughts were also coming together…
Let’s Talk About Becoming an EIR
Michael and I met soon after my return from vacation and we found ourselves immediately aligned with our thoughts about how I could put my experiences not only from Constant Contact but also from prior stints at IBM and Rational Software to good use with Underscore. That alignment revolved around spending time with the heads of the firm’s portfolio companies in the role as its first Executive In Residence. This role allows for the portfolio entrepreneurs to have an additional resource – me – within the firm to whom they can turn in addition to the Core community. My involvement will ebb and flow with them over time with greater focus on a few who are ready to really dive into formulating, understanding, and shaping their repeatable business model – something I know a few things about – also known as their “Funnel”.
At the same time, I will continue to meet with other founders, CEO’s, and key members of the Boston Tech Community as part of my learning and sharing process and bring back those learnings to help the members of the team. The EIR role allows me to give back to the Boston Tech community which is extremely important to me personally as it has contributed greatly to my success. This aligns perfectly with Underscore’s mission driven reality as well as with the Startup Secrets program.
It’s amazing to think back to four months ago as I started my journey of figuring out what was next for me and my career. That journey continues today. At that time, the only certainty I knew was that I truly wanted, no I needed, to find something that would help me keep that passion for helping entrepreneurs alive. At Constant Contact I had the opportunity to work with thousands of risk taking and high impact SMB founders. Now with Underscore, I have the opportunity to expand that passion and work with entrepreneurs who are creating new industries, defying the rules, and inventing the future of technology in the marketing technology field and beyond. I am honored to have been part of the team that made Constant Contact the homegrown anchor company that it came to be in Boston. Now I am excited to help the next generation of great founders create the next anchor company in Boston as part of Underscore.