Dear SaaStr: What Are Your Top 3 Pieces of Advice for a Young, First Time VP of Sales? I’m Just Turning 30
A few top mistakes I see with first-time stretch VPs of Sales.
1. Don’t lower the bar on hiring.
Almost every first-time VP of Sales does this, across almost every portfolio company and every startup I’ve worked with. The pressure is on the day you start as a new VP of Sales. The clock may be ticking to get some AEs and SDRs in the door, but you are still better off making sure whomever you hire is truly strong enough. Way too many first-time VPs of Sales I see make check-the-box hires — often because they aren’t sure they are senior enough to attract top talent. But then those hires often perform worse than the handful of existing reps. This is especially risky for any first-time VP of Sales who has never built a strong team under them before.
2. As you scale, you’ll have to hire managers better than you. And often more experienced.
If you want to scale past 18-24 months as a VP of Sales, you are probably going to have to hire a few managers under you that know more than you, and are arguably “better”. But if you don’t, you won’t be able to scale. Yes, that’s hard. But it’s the job. You’re the boss. Your job isn’t to know everything and have every single skill. That’s why you’ll have to hire a few managers under you that do.
3. Be positive but honest with the CEO
Way too many VPs of Sales, first time and 10th time, overpromise to the CEO. And / or hide misses. It only makes things worse. Be positive but transparent. If the CEO doesn’t have your back — then at least you know. Too many first-timers especially try to hide things when they fall behind. Or make crazy promises they’ll make up the gap in Q4. This just leads ultimately to an exit — for the VP of Sales. Don’t Hide Stuff.
And a few related tips:
4. Do a Real 30-60-90 Plan. And get the CEO to Agree To It.
Many founders skip this and don’t push anymore. That doesn’t help you. You’ll start off disaligned without realizing it.
5. Know the Product Cold Before You Start
There just isn’t time to wing it once you start. Don’t start until you can truly sell it yourself. Push off your start date, if need be. It’s better.
6. Get the CEO To Give You a Prospect Meetings-Per-Month Commit
Say 10 meetings a month, 2.5 a week, she’ll join. Too many founder CEOs exit sales once they hire a VP of Sales. That’s bad for both of you. So get a commit. To attend 10 customer meetings a month on Zoom, and say 6 a quarter IRL. You pick the meetings, they come if they can. This is magical. It really, really works.
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