So this is the real start of the VPs-of-Sales Lose Their Job Season.
Why? It takes until about now in the year for founders and VC boards to process both what happened last year and to align on if this year is on track. Around now, it dawns on folks the VP of Sales they have may not be the one they need. At a minimum, this is the time of the year it’s discussed.
And VPs of Sales know it. It creates constant stress in the role. Every VP of Sales knows around now, they are at risk of getting topped (someone hired above them) or even pushed out. And in fact, many VPs of Sales that hit or exceeded their number are still worried. There are just too many horror stories about VPs of Sales that did an incredible job and still were pushed out.
So be aware no matter how grateful you are and how well you treat your VP of Sales, and how well you think they are paid, and no matter how well they’ve done … they are worried. They all are.
A little of this may be good. But too much isn’t.
What can you do? Just a few thoughts:
*Have a CEO-VPS conversation about how far they can go. Do this once a quarter or at least 2-3 times a year. Be honest. E.g., “I’m confident you can get us to $20m ARR, but after that, we might need to bring in someone more seasoned.” This can feel like a tough conversation, and at a minimum, it may be uncomfortable the first time. But the best VPs of Sales come to appreciate it. A bit more here.
* If it’s true, tell them they have a management job for life. If they are so integral to the team, you want them forever — tell them. More than once. Tell them it’s possible someday you’ll need a CRO, but they’ll always have a senior role. This won’t make them immediately feel better. But they will remember. Some of the very best stretch VPs I know may have a CRO above them today, but are still VPs of Sales or even SVPs of Sales at SaaS companies worth $1B-$10B or more.
* Help them see the talent they’ll need to bring in. A great stretch VP of Sales often stumbles a bit when they need to bring more seasoned folks in under them as managers. They most often stumble when they have to hire managers more senior than them … to work for them. Tell them why that will be important and help work with them to get there.
Look, VP of Sales is a really hard job. Because every quarter, sometimes every month, you have to do even better. Even when last quarter was epic. It weighs on you.
Even worse, at the same time, you have to worry about your job.
If they’ve done so well, they’re got a job with you for life … just tell them. It will go far.
