Lifers, FBI guys, and Acquired CEOs

Since I’ve had the good fortune to work at small, large, and small-that-became-large software companies, people sometimes ask me about the pro’s and con’s of working at companies of different sizes.

Let’s start with the basics.  At a small company:

• You generally see more of the business and can learn more horizontally.
• You typically have more opportunities for vertical growth (i.e., moving up the chain within your function), particularly if the company is growing quickly.
• You can often, but certainly not always, make more money on the stock.  Though be careful about assumptions here, I’ve seen small companies that are very cheap with stock and I’ve seen big ones where a GM can roughly equal a startup CEO in terms of equity upside, and with probably higher expected value (if lower variance).
• You are more hands-on, doing things yourself as opposed to working through others.

At a big company:

• You can learn more deeply, as large departments are typically filled with deep experts in their domains
• You get leverage, both in the sense that you can drive programs through others and that in the sense that things are driven for you.  For example, at Salesforce, the amazing customer briefing center machine made it so I could see 3-5 customers / week without leaving the building.  What a great baseline from which to build.
• You spend relatively more time selling decisions and relatively less time making them.  This can be frustrating if you are the kind of person that, once convinced, wants to go execute.  It can be fun if you like selling ideas internally.
• You have more opportunities for lateral growth.  At larger companies, I’ve seen the customer success leaders moved into sales, product managers moved into sales ops,  or product marketers moved into HR.  The basic pattern is that once proven a “great person” then a big company is typically more willing to let you try something new.

The biggest disadvantage of bigger companies relates to power, access, and the ability to get things done.  Based upon my own experiences (and a recent coffee with an old friend), I believe that three — and only three — types of people have any real power at a larger $1B+ software company:

• Lifers.  The inner circle of top managers who have helped build the company and who possess a vast institutional memory.  The more the CEO is  him/herself a lifer the more powerful this group.    For a newly hired executive, this can be a very difficult group to penetrate because the trust, relationships, and shared experiences have often built up across a decade or more.

• FBI guys.   Companies hire FBI guys when they are either in trouble or simply distrustful of the ability of the lifers to scale with the business.  I call them FBI guys because they are seen as proven experts, and assumed more qualified than those who built the business due to their previous experience in larger companies.  The most non-nonsensical example of this I ever saw was at BusinessObjects when we hired the head of BI from a mega-vendor to a key position on our product team.  (I protested:  “isn’t this the person we just beat over the past decade, despite their having every structural advantage over us?”)    The more common flavor of FBI guy is the entourage that often travels with a new executive.  The other reason I call these people FBI guys because of this scene from Die Hard which reminds us that things don’t always work out so well when you bring them in.

• Acquired CEOs.   The only other group I’ve seen that consistently has power is the CEOs of acquired companies.  This group has power for several reasons:  (1) because they are often highly expert in their area, (2) because they are seen to have vision and/or dynamism that their big company peers may lack, (3) because the company wishes to retain them beyond the expiration of any handcuffs, (4) because they may have been acqui-hired in the first place, and (5) because some big companies feel like they can “stay young” by injecting entrepreneurs into their corporate bloodstreams.

So let’s distill all this into a few rules.

• If you’re a lifer, great.  Don’t take for granted that you’ve been a key part of building a great company.  As I used to tell friends who I thought were leaving BusinessObjects too early:  “good waves are hard to find; if you’re on one, ride it to the beach.”  At some point I’d argue that you probably should leave, try something new, and challenge yourself — but do that only once you’re sure you’ve gotten 90% of the value (both learning and money) that you think you can get.  Meantime, be nice to the new executives (except the FBI guys) as you probably can’t easily understand how hard penetrating the group can be for them.

• If you’re an FBI guy, be humble.  No one likes people who show up with all the answers.  Ask questions for your first 90 days instead of preaching about what worked at BigCo.  When you start implementing decisions, explain from first principles why you think they are good ideas (and never say “because we did it this way at BigCo.”)  Don’t be exclusive and hang out with the old BigCo gang only or spend hours telling the BigCo stories from the good old days that are meaningless to most of those around the  table.  Don’t compare the past to the present because you weren’t there in the past and definitionally can’t know how things really operated.

• If you’re an acquired founder/CEO, then go make your impact.  You may have significantly more power than you know.  Go leverage it to make a difference.

• If you’re weighing career options, don’t forget to map your memories to your past role.  If you loved being a lifer at your last company, remember that in joining a new one you’ll be a new guy.  If you were an FBI guy, brought in by a new CEO, remember that unless you’re traveling together again, that you’ll just be a regular new executive.  If you were an acquired CEO who had a great experience at the big company that acquired you, remember that if you just hire-on that your experience may likely be different.