Getting to Initial Traction

10 Rules to Being a VP of Sales in a Startup

brendoncassidy2005@yahoo.com'

Brendon Cassidy

Brendon Cassidy, my VP of Sales (who you should come hear speak at the SaaStrAnnual.com!) wrote a version of this piece a while back.  It had 2,398 likes and clearly hit a chord with people.  I though an updated version of this would be good for founders thinking about hiring a VP of Sales … VPs of Sales themselves … and VPs-to-be to read — Jason, ed.

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10 Rules to Being a VP of Sales in a Startup

  1. If you come from a large software company, don’t implement their methodology. It isn’t going to work in a startup. Literally 100% failure rate. Let go of what you know. Listen. Learn. Adapt. And get moving. I went to a startup once where the prior VP of Sales had 13 opportunity stages with an average deal size of 6K. Nope.
  2. Have an open mind around hiring. Hiring folks from Oracle and SAP who do million dollar deals selling 100% into their installed base probably aren’t going to be a fit for you. In a startup, million dollar deals are few and far between. And the amount of time you have to wait for reps to “chase” those deals just isn’t worth it. You need customers. You need revenue. You need to build some repeatability. Hire great talent, not great resumes
  3. Keep it simple. Trying to make it more complex in a startup creates more excuses for failure. Make your pricing plan simple. Make your pitch/presentation/messaging simple. Black and White. Understand where your strengths are and sell to your strengths. Understand your weaknesses and use them to your advantage.
  4. Screen Shot 2015-09-22 at 3.11.10 PMBe incredibly passionate about the problem you are solving and the solution you are solving it with. Taking a VP of Sales job in a startup “for the paycheck” just isn’t going to work out. You need to own this thing. It is your baby. Late nights. Weekends. Always on the grid. You have to BELIEVE. It’s the only way you might actually SUCCEED.
  5. Try to pick a founder/co-founders/CEO that you are compatible with. For me, I look for someone that I know will support me in good time and bad, because it ain’t gonna be all roses. There will be spectacular highs followed by excruciating lows. Knowing your CEO has your back, for me, wow. It makes all the difference.
  6. You need to know how to interact and collaborate with engineers and product managers. This isn’t Oracle or Salesforce. Sales is important but the engineers are just as important. Maybe more so in some cases. If you get cast as the stereotypical sales VP, then they will not respect you. And they won’t build you what you need to succeed. Engineering and product is your partner. Having a great relationship with them is vital to your success.
  7. Understand that 90 out of the 100 startups you talk to are going to fail. And that is a conservative number. They aren’t going to make it. It’s going to end in a firesale, an asset sale, or some kind of sale where nobody makes any money. I started my career as a tech recruiter, working exclusively with venture backed startups from 2000-2003. It was a great training ground to learn how to handicap a startups chances for success or failure. If you think 50% of the startups you look at can win, then you need to surround yourself with people you trust who will help steer you right. Be forewarned.
  8. Be a hero. But don’t try to be a hero. Make good decisions on who you choose to work for. Use common sense. A SaaS company with a $3,000 ASP and less than $1 million in ARR on $40 million raised. Good night Irene. Generally, if the financing to ARR is 1 to 1, you are golden. Understand MOST won’t have 1 to 1. But if you find it…they need to go to the top of your list.
  9. Pay your sales people. Pay them above market rate. The only way good people are going to come to your company is if you pay them a high commission rate. You can do all that and make your sales org a highly profitable business. Being cheap and unheard of…you tell me if that sounds like a winning formula.
  10. Your team’s success is your success. Your job is to create a structure and culture that breeds success and hopefully…you know…some fun. But don’t take the credit away from them to shine the light on yourself. Nobody likes that guy. And nobody is going to want to work for you again. Set them up to be successful. Pay them when they are successful. Help them understand what it takes to succeed in your sales organization. They need to feel like you are there to help them. You aren’t here to refresh spreadsheets in your corner office.
Published on December 23, 2015
  • Brendon has highlighted some great topics. I echo his feedback regarding established reps that start-ups hire thinking they are the ticket to success. The challenge is, although these reps. look great on paper, they are not the right fit. I’ve worked with many start-ups who went the established rep route only to let them go because they don’t know how to evangelize emerging technologies and solution sell. There is the idea of what is called the Renaissance Rep. This is some one that has experience with start-ups, that is more of a hybrid rep. More to come…

  • I think Brendon had a theme going and that theme was that a startup is unique and your thinking and strategy has to be as unique as it is. That is why it makes me crazy when companies look at other “high growth” companies and say… let’s just do what they are doing. Duh…… never works. Yes it is interesting to understand their benchmarks but rarely should the implementation be a mirror image. Buyers, markets and solutions are the variables that dictate a go to market strategy. #variablesmatter Thanks for this piece. Very thought provoking and informative.

    PS – Looking forward to your book release!

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