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Finding Your Soul Mate

I am certainly not one to give real dating advice based on current experience, um…perhaps based on any past experience as well, except for, thankfully, my last attempt….

But in the last few weeks, I had some catch-up conversations at conferences and elsewhere with old friends, peers, and favorite members of past teams that I’ve led, that reminded me of what the challenges can be in searching for that next great full-time job or consulting client.

Both search processes have some analogies to how venture capitalists vet companies to invest in, and I wouldn’t be doing justice to say these guidelines are as well developed as leading VCs who have been in our space since the beginning. But here are three things that should stay as most important throughout:

Is There a There, There?

This one’s tough. Really tough. I’ve seen slides in a deck showing just sketches of what’s being built, and then see it get built, ahead of schedule. And I’ve seen working demos of something that looks like it’s already in-market, and it doesn’t get finally out to launch with customers or an audience for at least nine months, an eternity in the ad tech or digital media world. If you are senior enough and playing a critical role to a company’s success, you should offend anyone by asking for the product roadmap, or at least highlights of it, after you sign your NDA. Go look up what product people have actually built before. Then ask at least two potential or existing customers what they think of the core offering. If it’s a great idea with no set market yet, hope they’ve raised enough cash to have the market get ready for them or to have the time finding the right existing market.

How is their company brand?

Just like any ad campaign, having a sense of current brand awareness and perception is key. Yes, we all think our arrival at a company will completely change everyone’s view of that company or put that company on the map. If you are becoming a CEO, COO, or in many cases CRO, then yes. For everyone else, get real feedback. Find people you know in common with the executive team, sales team, anyone at the company, and ask what they think and have heard. Read the press, not the press releases, and the comments section (taking the anonymous ones with a giant grain of salt). And picture yourself at industry events talking with colleagues or with friends anywhere about what you will be doing and where you went. It’s not that we always go by what everyone else thinks, but at least factor in what their reaction will be and what questions they’ll ask you about this new job or client.

How are the People?

Always the most important. I made a couple of mistakes over the years working at companies that had great product, great-sounding product, or great industries/processes to interrupt, only to learn that it takes great people to lead and actually execute at those companies to be successful. We have seen enough pivots in the ad tech space alone to realize that strong CEOs, COOs, CROs, and boards know how to find a market, even when developing and shifting quickly, and fill a need fast with something truly unique and valuable. Make sure your potential client/new company has people that have actually run a company before, or at least managed people at some serious level. It certainly helps the company burn rate when the CEO is also the primary coder. But with rare exceptions (see Zuckerburg, Mark) that are brilliant in their field but also smart and humble enough to bring on well-seasoned executive talent at the right time (see Sandberg, Sheryl), many top engineers and product people discover on the fly that recruiting and leading people and running an entire operation are skillsets all unto themselves.

It is amazing how anyone staying three years at the same company these days in digital media or advertising technology is often now considered a “lifer” because of how many cycles and evolutions a company can go through. Look yourself in the mirror and feel very confident about answering those three questions above before taking that next plunge down the aisle. And you’ll have a better chance of your next full-time job or consulting relationship lasting longer than these two sweethearts did.

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