One of the partners from General Catalyst, our investor, asked me to join a breakfast next week with a bunch of VP's of Sales who want to get to the Ceo level. I grew up through the sales ranks and was a VP of sales prior to being Ceo of HubSpot, so I guess I was not a bad target to join the discussion. In between Red Sox games, I spent a few calories thinking about some of things I could share with those folks and thought I'd share them with our readers as I suspect many of you might be vp's wanting to be ceo's some day.
Here are a few of the things that worked for me or I think are relevant to think about if you are a vp aspiring to the corner office.
Entrepreneur-In-Residence/Venture Partner -- The very best way for a vp to find a great company to join, is to become an EIR at a venture fund. There are two benefits to this. First, you get to see many more companies who are in need of a ceo than you would be able to do on your own. Second, you get to see how deals are funded from behind the scenes. Learning how to raise funds is typically a gap in a vp's resume looking to take a ceo slot. I was a venture partner (same thing as an EIR, typically) at Longworth Ventures before starting HubSpot.
Join a "B" deal or start an "A" deal -- Before starting HubSpot, I was looking at several deals on the East coast and was interviewing for ceo slots. After going through this a bit, I started to realize that I was going to get offers from "B" list companies, not "A" list companies. A "B" list company is typically a Series A deal funded by a second tier venture fund or a re-start (struggling company with a net new management team) funded by any venture fund. The "A" list companies were hiring folks who had been there done that in the ceo job before.
I decided I'd rather start my own company and turn it into an "A" deal, rather than join a "B" deal. That decision has worked out exceptionally well for me, but it was rather risky at the time. For those of you like me, I would strongly consider the option of partnering with someone and making your own "A" list deal, rather than taking your first ceo job with a company with a lot of warts on it.
Sloan Fellows MBA Program -- I had always wanted to get my mba, but from a timing perspective, it never seemed to make sense. I got particularly lucky to have joined PTC right out of college and had a phenomenal run with a high flyer for a relatively long time. Before I knew it, I was too old to get my mba and also had a burn rate that would not have enjoyed two years without working.
One of the smartest things I've ever done was join the Sloan Fellows MBA Program. A typical mba program starts in september and runs through June two years later -- you are in school about 14 months out of 21. The Sloan Fellows Program was designed for folks like me who were mid-career and could not afford to take two years off, but still wanted the rigor of a full-time mba. The program starts in June and ends the following May (12 months). The program puts you through an intense bootcamp over the summer where you do double time on classes. In September, you basically join the second year MBA's and finish out the school year with them. You end up doing the same number of credits and learn all the same stuff, but they let you do it without all the downtime.
I got three benefits from the program. First, I got some Sloan/MIT pedigree on my resume. Second, I learned a ton, particularly about finance, which was a complete black hole for me. Third, I met a fantastic group of friends/colleagues who are part of my network now and forever -- we have six Sloan grads on HubSpot's team!
The truth is, I think the mba truly helped me to get ready for my current role. I think it's highly relevant to you if you are a vp looking to be a ceo.
There is a Sloan Fellows Program at MIT and something similar at Stanford out west. I recommend doing one of these two relatively unique programs, rather than doing a part-time or remote mba.
Some VC's Prefer First Time CEO's -- At the end of the day, the ceo works for the investors in the company and is picked by the investors. Some investors have a reputation for backing first time ceo's because they are hungrier and they have had good success with them. Other investors have a reputation for never hiring first time ceo's. This tendency can sometimes be venture fund-wide or be relevant to different investors within a fund. It is worth your while to find out who has these tendencies and it is probably worth your while to investigate an investor's portfolio companies before you interview with them.
I went to General Catalyst's recent ceo offsite in Newport and was surprised/pleased to see that many of my peers were also first time ceo's.
Surprisingly Powerful Headhunters -- While I was at Longworth, I was surprised to see how important executive recruiters were in the search for a new ceo. For the most part in my career, I had discounted executive recruiters because I was a little skeptical of the abilility of some of them to qualify me, so I always figured that the hirers would be as well. I also thought that the hirers were so well connected, that they would always tap their network first.
It turns out that headhunters provide a very valuable function to the hiring of a ceo. Typically there are multiple investors and outside board members involved with the hiring decision all with their own biases and candidates. The executive recruiter comes in and is the impartial third party that takes into account all the biases and comes up with a relatively short list of folks to interview, over and above the folks the individual board members put forward.
It's worth it to take the meetings with the executive recruiters because their opinion matters, especially when coming up with the short-list.
Don't Try To Be CEO of Your Current Company -- I would be careful not to try to be ceo of your existing company. There are generally two ways that the corner office opens up.
The first way is that you/others have worked hard to undermine the current ceo's credibility and he or she ultimately gets ousted in a coup de etat. In this situation, you probably will not be picked as the current ceo as you'll be seen as being too Machiavellian.
The second is that your company is in trouble and the ceo gets fired. If he gets shot, it's unlikely the investors are going to want to promote someone from within the organization. In this situation, they often prefer an outside change agent to help re-start the company.
The best thing you can do is put your head down and do a fantastic job where you are and help your exisiting company prosper. You are much more likely to be picked up as a first time ceo if you were vp of sales at a company that had a great exit than one that imploded with political infighting. In fact, you are much more likely to get more credit than you deserve if your company has a good exit.
Those are all the thoughts I had on the topic. If readers have other tips/ideas on what they think helps, please leave them in our comments section.
