You’re an Operator and Maybe Don’t Even Know It

Many concepts in Silicon Valley are defined from the point of view of the venture capitalist (VC), not the employee or founder.

For example, the term “exit” is a misnomer when seen from the employee point of view. An IPO is usually anything but an exit for executives who first will be subject to a 6-month lock-up period and restricted to certain trading windows thereafter. A PE acquistion is usually not an exit for the executive team who may be expected to stick around, sign employement letters as a condition of the sale, and rollover a certain percentage of their proceeds into the deal. These transactions are, strictly speaking, best described as an “exit” only for the investors.

So it was with great one surprise one day, a decade or so ago, that I learned I was not a CEO, but an “operator,” when seen from the viewpoint of a VC. Frankly, I found it odd to be referred to as an operator, but I hoped that at least I was a smooth one.

From the VC point of view, there are four types of people:

• Founders. The entrepreneur(s) who found a company.
• Operators. The executives who build and run companies
• Investors. The venture capitalists who invest in startups.
• Employees. The 95%+ of the staff not on the executive leadership team (ELT) but who, paraphrasing George Bailey, do most of the working and paying and living and dying in the company.

So, what might you do with this morcel of knowlege? While I believe that the mere act of trying to see things from others’ viewpoint is always developmental, there are some practical takeaways here.

Let’s assume you’re an operator. What should you know and do?

• You are not a founder. Many operators, particularly ones who join early, start to think of themselves as one of the founders. While the founders may even treat you as such, from the VC/board point of view you are not. The founder invincability cloak does not apply to you, no matter how much you’ve contributed nor how much you are valued. You are an operator. You may be beloved, but your replacement is always one phone call to 1-800-DAVERSA or 1-800-HEIDRICK away. Don’t overplay your hand. Some do.
• You are valued for different things than a founder. Boards value operators for their experience, common sense, reliability, and professionalism. If given only one adjective, I’d say board members want “brilliant” founders, but “solid” executives. Operators are not creating the vision; they’re executing it. I don’t need an artiste to replace my fence, just an experienced fence builder. Be solid and low drama. This doesn’t diminish your value in any way: such operators are often quite hard to find.
• You are positioned by expertise and sub-expertise. You are a velocity sales leader. Or a big-deal CRO. Or a demandgen marketer. Or a CRM product leader. You become what you repeatedly do. Actively manage your work so that you position yourself where you want to be. If you want to be positioned as an ABM marketer or a post-agile engineering leader, then go lead an ABM marketing or post-agile engineering team.
• Fighting positioning is pointless. Positioning works because the human mind likes to simplify. If you think you can position yourself as the SMB and enterprise, transactional and artisanal, process-driven and relationship-driven sales leader, then you are mistaken. If you fail to position yourself, don’t worry, the market will do it for you — you just may not like the result. Actively position yourself and don’t fight the tide in so doing.
• You are positioned by size-range. Think: we need a $10-30M CRO. Or a $30 to $150M CFO. Or a $100M to $300M CEO. The size ranges aren’t fixed, but be aware of what size range you’re positioned in. Avoid the number one mistake I see: leaving a high-growth company too soon because you’re tired of something, thus leaving yourself positioned as a $10-30M operator when — if you’d held on for a bit longer — you might have been a $10-100M one.
• Expect to get hired below the top of your size range. No patient wants to hear, “this is the first time I’ve tried a brain surgery this complex, but I’m really confident I can do it.” Expect VCs and boards to think similarly. If you’re positioned as a $10-30M CPO, don’t expect to get hired by a $30M company growing to $100M. Expect to get hired by a $10M company growing to $30M. Per the prior point, ride existing success to increase the top of your range. And beware anyone willing to hire you above it.

I’ll use myself as an example of some of these principles:

• Despite having been CEO of two startups from $8-50M and $0-80M for over a decade, I am still widely positioned as a marketing guy. I embrace that both because there’s no point in fighting the tide and I think it’s true. I am a marketing guy. It’s my DNA. I ooze marketing. But I try to remind people of my overall experience with my 10/10/10 message: 10+ years a CMO, 10+ years a CEO, and 10+ boards.
• Despite having been CMO of a $1B company and SVP/GM of a $500M business at a $3B company, I get positioned as an early-stage guy, and get size-bucketed in the $0-100M range. While I am certainly strong in that range, I have both signficant experience and clients well beyond $100M. While I can find work beyond that range and enjoy doing it, as a marketer, I must accept that I can’t position at both ends of the scale. Positioning is all about choice and, as the saying goes, “if you try to be everything to everybody, you end up nothing to nobody.”

Or, as I like to say to marketers in career planning: marketer, position thyself!