Why do early stage companies struggle to hire and retain the right revenue leader?

There are two consistent mistakes.

(1) Hiring the wrong fit. For example, you have two AEs and a BDR in the team, and you hire a 25 year veteran with fantastic leadership experience. That individual may not want to get into the weeds of, eg, reviewing BDR emails. Maybe they haven't been close to the BDR function for years. You also need them to close deals themselves including by generating pipeline. But if you don't have the right person, instead they want to hire a team, build plans and engage with the Board. They simply don't get enough of the work done at the coalface, and you lose 12 months in sales development.

(2) Not knowing how to manage a sales leader. If Sales is not your expertise – and it very rarely is for a founder – how do you know what goals to set? (It's not just a revenue number.) How do you hold them to account without micromanaging? Most critically: How do you know that a lack of sales is due to the sales leader not some other cause(s)? Revenue is a company problem – and there are many reasons it may not be coming, of which the sales leader is only one option.

Both of these problems can be solved. Careful consideration of what you actually need the sales leader to do is critical. Hire for the next two years, not for the next 10. The job description will possibly lead you to a more junior, but experienced, sales manager. Interview robustly – not an easy skill to learn from first principles. Once they're on board, have clear company goals for the next 18 months, that drive sales, marketing, product and engineering.

I have tools available (for free) to help with all of this. Let me know if there's anything you would like to get your hands on.