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#26: Start-Ups Hiring Their First Sales Leader Have a Lot to Consider

Updated: Aug 16

The start-up that hits on hiring their first sales leader will substantially increase the probability of generating an asymmetric return.


Shoutout to Andreessen Horowitz, especially Peter Levine for consistently publishing high value content focused on this area, growth, intersection of sales and marketing etc. + #MiamiTech. Both inspired this essay.


6 important considerations below:


  1. Can one of your co-Founders sell as well as the other can build product?

  2. Goes without saying but one co-Founder has to be a monster on the product side of things and another must be able to sling it.

  3. How clear are you on your go-to-market-strategy?

  4. There is a common misconception that "Enterprise sales is just enterprise sales.

  5. It's all the same, you just need to find people that know how to do it."

  6. Selling a 4 vs 7+ figure investment into one type of enterprise vs another isn't the same thing.

  7. The buying committee seniority, focus, priorities, perspective etc are different.

  8. Never underestimate the importance of nuances.

  9. A Sales leader that respects + collaborates effectively with demand generation will lead a team that will generate 2X+ the revenue of a sales leader that doesn't

  10. Oversimplifying but sales is the customer of the demand generation team.

  11. If sales + demand generation are locked at the hip, $1 in, $10+ out.

  12. Not all money is green

  13. This might sound counterintuitive but pursuing + getting deals done with the right prospects in it for the right reason is critical.

  14. While rolodexing is phenomenal, it's critical that the sales leader brings more than just that knowledge and access to the table to avoid false positive market signaling.

  15. Culture is everything aka Mike Tyson Rule

  16. One of the worst reputations sales leaders earn every single day is the negative impact they can have on a company's culture.

  17. There is no doubt, bringing in a sales leader will impact your culture.

  18. The founders along with the sales leader can ensure the impact is positive or negative.

  19. Ensuring its seamless and positive is beyond critical.

  20. It's a choice.

  21. Heavy is the crown.

  22. Bottoms-up sales approach is great but enterprise deals don't close themselves

  23. Importance of bringing in someone who can toggle between top down vs bottoms up, carry a bag vs lead a team, Sales vs Demand Generation, net new logo hunting vs organic growth, process strategy vs tactical implementation / iteration, securing a champion vs navigating senior buying committee, talent recruiting vs talent development etc


March 6, 2021 (Tweet Link)

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