Startup Sales Leadership: The Good Fellas Mind Set

First, the video. BIG TIME WARNING: There is profanity in this video and I am warning you now to not watch the video if you are offended by cursing. I know that posting something with cursing is risky and I could lose some of you. I hope not, but I understand. Here is the thing — when I run into the issues that I am about to detail in this post, I think of this scene. I just have to present it as is.

I am surprised I even need to write this. The one thing I love about sales and sales leaders is single-minded pursuit of the number. Unfortunately, I have spent a lot of time with b2b startups and I have seen this really weird situation: The sales leader is spending his/her time on the wrong things and the results are a disaster. Sounds weird right? We think of sales as voracious sellers…they can sell the Brooklyn Bridge and can’t wait to get out there. Not always the case. Let me give you some use cases:

  • I was recently at a startup (2 sales guys) where they hired a veteran b2b sales leader. The sales leader spent lots of money and time setting up, getting the preso ready, etc. Now this is fine, except with 2 guys, this should not be a 2 month project. But more importantly, he was telling the CEO that he would not sell until all the pieces were in place and the product wasn’t ready (it was ready, they had customers already using it. It wasn’t perfect, but there was something to sell). He spent very little time on sales calls or even working deals because he kept complaining “they weren’t ready”. Sales guys were following up on leads but with no direction, were getting a couple pots and pans deals here and there. I told him: “Dude, you gotta sell something or this won’t be good”.  He disagreed. He was let go in like 3 months.
  • My buddy is consultant and was working on a project with 5 field reps already in the seat. The VP of Sales was spending all his time having him install all this technology before they had even sold anything like a complex sales compensation application that “he had at his old company” (which had 200 sales reps). No activity happening in the field. No idea what was going on. I used to run into this all the time in my days at SalesRamp. The sales leader spent all this time setting everything up and not beating the street.

See the issue? That’s not going to work.

Follow the GoodFellas motto and always keep your eyes on making it happen. Here is some food for thought:

Reality check: The solution you are selling is incomplete

Here are your warnings before you join: There are problems with the product. Yes, they misrepresented how far along they were. No, they do not have all these happy customers. If you join a startup, thats the game. This will be hard — know that before you join.

Be agile

I am certainly NOT the guy saying to ignore people, process, and technology. That is my livelihood. But lets be agile here. Start with a simple plan with simple process and absolutely must-have to sell technology. The CRM should be functional and basic…The product guys are doing. They go to market with the MVP (minimum viable product) and adjust accordingly. You have to do the same. In one of my old companies, I was working with a sales leader. First day on the job, I told him we could do a sales call at a buddy’s company but told him we could wait. We had a deck for investors that we had done one rev of changes for the sales deck. His response: “Let’s go. I’ll give it”. We spent 30 more minutes fixing it up and he went for it. It was on. I was inspired.

Sell what’s on the back of the truck

As sales leader you have to tell the organization what you need to sell. Conversely, you have to sell while they go fix it. The problems with the product are rarely a fatal flaw and if you bring in the right deal — they will fix it. There is someone you can sell it to. Focus on the good things and identify customers who need it. Start there. If you sell, the organization reacts. Just charge.

Do things that don’t scale

“Craig, that doesn’t scale.” Craig: “Well, you won’t be here when it does if you don’t”. One of the best posts of the last two years is Paul Graham’s Do Things That Don’t Scale. Startups love hiring guys from Salesforce or other great, successful sales cultures. They know how to scale. I love that so don’t get me wrong. But again, as a sales leader plan to go big but be prepared to do things that won’t work later to win deals and make people happy NOW. Be hands on as hell in the start. You can’t sit in the ivory tower yet. You gotta take 10 meetings a week, get into deals, etc.

Figure it out because you have to

That’s your job. The organization hands you an imperfect piece of art — you figure out how to go to market. PERIOD. I recently talked to my VP of Marketing buddy who was talking about their new VP of Sales. “He walked in and spent a couple weeks looking at the product, did 20 sales meetings, and met with executives. He then rolled out his plan. Stage one: we are increasing the price and selling only to companies with between 200-1000 employees. We will focus on this very specific set of problems. I request that the organization provide us with X amount of leads. In the meantime, we will get our own deals. I need the following product enhancements over the next 3-6 months. This is how we will deliver the number.” The company grew IMMEDIATELY and I love that guy for it. The VP of Marketing: “We would be out of business without him.” My man.


Exhausted yet? There are startup vp of sales who just get it done and I love them. I remember Bill Binch, early days at Marketo, telling me how when he got there he met with a rep who hit his number for the month. “What do you have for next month?” Rep: “I don’t think I will hit next month.” Bill: “Just to be clear: You have to. Let’s dig in and make it happen.” And you know how that story ends.

I love startup sales leaders who make it happen. It is so hard sometimes. You have to literally scratch, grab, and fight to hit early numbers. Many aren’t suited for it and unfortunately, people who have succeeded elsewhere can fail at startups. I’ll leave you with one more story: In 2002, I consulted for a sales leader at an early stage startup trying to find their way. He was a mean son-of-a-gun from Oracle. First meeting with the sales team, one of the sales reps complained that they were missing XYZ. His response: “We sold a billion dollars worth of Oracle Financials and it didn’t even work.” The secret that the sales rep didn’t know was the sales leader passed that back to the executive team as something they needed. He wasn’t being unresponsive, his message to the team was: “We won’t be stopped. No matter what.”

Remember, the board, CEO, and the rest of the company is thinking one thing: “F you, pay me”.

Another reminder!: This  Thursday April 17th from 8:30-Noon is the Funnelholic Virtual Sales Summit feat. Jill Konrath, Jill Rowley, Matt Heinz, and Dan Waldschmidt. Please click here to learn more. See you there!

Craig Rosenberg is the Funnelholic and a co-founder of Topo. He loves sales, marketing, and things that drive revenue. Follow him on Google+ or Twitter

  • Again, if you write me complaining about the swearing…I will agree with you. It’s not cool and I debated for awhile on whether to include. But it was my inspiration so I decided to go with it

  • Steli Efti

    Really freaking awesome post! Love it!

    I gave a “crash course in startup sales hustling” a while back that some might find entertaining/educational in this context