The summer is a great time to take a bit of a step back and re-asess one’s goals and priorities. In addition to thinking about your business with more of a blank slate once in a while, I think it’s also importan to take some time to think about one’s own development as an entrepreneur, executive, or investor. I’ve noticed that most of the entrepreneurs that I’ve been most impressed with have been very intentional about their own development, and are proactive about creating a plan to improve their capabilities as they progress through their careers.
There are a lot of ways to do this. But I heard a terrific example yesterday from my friend Mark Roberge, the SVP of Sales and Services at HubSpot. I loved his example because of how intentional he was and how he has shifted his efforts as his roles and his company has progressed through very rapid phases of growth.
When Mark started in his role, he had virtually no experience in sales and was largely an individual contributor vs. a manager of teams. In addition, the company was very raw and really just figuring stuff out. When he entered his role, he started off by interviewing dozens of other heads of sales at technology companies in various industries and stages. The goal here was less to find very concrete advice, but more to do a general survey of his eventual peers and try to glean some gems of wisdom from their experiences. It was very much a blank canvas approach to his role, and I think it’s an important thing to do regularly when you start a new role, or even to refresh your perspective on your current role.
As Mark progressed and his team grew, he established a regular gathering of peers that would meet every month and discuss specific challenges and learnings as they each progressed through their careers. This group was hand selected, and each member was, like Mark, a head of sales of a rapidly growing, successful technology company. I’ve heard of a number of similar initiatives as this, and I’m a fan. I encourage founders in our portfolio to try to create peer groups to help one another develop, and in some cases, these groups are moderated and have a relatively hefty membership fee. My friend Brian Balfour, the co-founder of Viximo and Boundless has talked about the value of Core Peer Groups before, and also organizes a group around large scale customer acquisition that has been very fruitful for him and others.
Fortunately, Hubspot has really grown to be a pretty significant company, and Mark’s role has grown to be a manager of directors, of managers, of individual contributors. His team numbers over 200. As his next stage in development, he sought out a more direct mentoring relationship with a senior sales executive who had held this role at a number of public technology companies and was in the “time to give back” stage in his career. Mark meets with this person for half a day each month in an effort to scale to the next level.
I thought Mark’s example was a terrific example of someone who has done some simple but effective things to continually improve himself. As the summer comes to a close, I’d encourage all entrepreneurs to try to think through some specific things they could do to get themselves on a path of continuous improvement.