• Dana Hillman

"Known knowns" for VP Sales Candidates

Sales VP’s & Directors for Start-ups

Over the years, early-phase tech startups have littered the roadways with first-in VP’s & Directors of sales at a steady clip. Many fail or get pushed off the bus due to unrealistic expectations, bad skillset fits or mistiming the market. If you’re an investor, startup CEO or candidate, due diligence is important for both parties, but as Donald Rumsfeld would say, “There are known knowns, known unknowns, and unknown unknowns.” Yea, I know . . . quoting Rumsfeld is a slippery slope, however - shock and awe mysticism aside - here are the “Known knowns” for VP Sales Candidates:

It’s Friggin’ hard . . .work/life


One could say euphemistically that early phase tech startups are unique. Realistically the movie “The Revenant” is a more accurate depiction - only without the snow and the fabulous fur wardrobe. If the Grizzly mauling scene strained your diaper tapes, then a board meeting with contentious investors picking through your pipeline will cause them to rupture. Know your tolerance for pain and be realistic. If you’re looking for work/ life balance, quality time with your family or a “New challenge”, then look somewhere else. Startups are gloriously messy and painful. Like rehab or Army Ranger school . . . people only say a startup “Was the best experience of my life” when it’s been successful and in their rearview mirror.

Most don’t work . . .


Everyone wants a “Home run.” No one would be in a startup if they didn’t, but base hits and doubles are important and much more likely. Don’t evaluate a company based on being “The hottest new company,” or on technology alone. Instead, focus on determining if they’re solving a problem that customers will actually pay to have solved. Oh yeah, smart money and a seasoned executive team don’t hurt either, however, be aware that the opportunity for “Name brand” VC’s and Exec’s to fail, always exists too. Keep in mind, that these days, huge disruptive infrastructure deals aren’t the norm. Point products that solve a specific problem - products that will eventually end up as part of a larger solution - are much more prevalent. Many are incredibly meaningful, others are “Solutions looking for a problem to solve.” Keep in mind that if you’re close to your customer base and the technology is in your strike zone, you may be a better judge of the market; you may well find interesting companies that traditional venture firms can’t wrap their head around. Trust your gut and your research.

Qualify yourself and the company . . . really hard


As a first-in VP or Sales Director most likely there is no pipeline; if there is a pipeline you’re inheriting, that may be worse. You’ll have to qualify existing pipeline like hell, and test your customer relationships first if you’re starting from scratch. If feedback is positive, keep talking. If not, take a pass and move on. If you don’t have customers in the target market to call for input in the first place, then do your own sanity check. An understanding of the technology and strong relationships in the target market are a must. If you don’t have that, then it doesn’t matter how hard someone chases you, if you take the gig, you’ll likely be roadkill.


If you’re talking to a later stage company and they’re interviewing you to replace someone else, find out what went wrong. Make calls and check out your would-be predecessor. A CEO or Founder will rarely call the baby ugly, however, in many cases, they may say it was a “Sales Issue.” Keep in mind that most good Sales VP’s or Directors don’t turn into lepers overnight. If you hear “Sales issue,” there’s always more to it. At best the team committed one of the cardinal sins of hiring someone based on past glory, someone from a different market, a referral from a friend or board member or just poor vetting. At worst the product may not work, they may be too early or too late, they may be solving a problem that customers don’t have or they’re about to get rolled by an incumbent. Be relentless and find out, your career depends on it. Seriously.

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