This post by Jake Dunlap focusing almost exclusively on first time VPs (Stretch VPs) and aspiring VPs is too pertinent not to repost. You can find the original article on LinkedIn here.

I was sitting at JFK the other day and had a realization – too many sales leaders punish themselves because they feel they aren’t good enough when in reality they are playing a game that’s tough to win. 

I first posted five tips of the for being a VP Thursday morning and had an overwhelming response. I knew people would feel strongly (one way or another) about some things that we often don’t say out loud and do a mental sweep under the rug, but the response prompted a second post with a 6th tip and then a video with 3 more. This lead me to compile it into a full cheat sheet and share some great insights from the comments.

You may be that VP or aspiring VP that shrugs and thinks “That’s the name of the game we hate and love,” but if you want to move more into the love half of the game, tuck this advice into your back pocket to go back to whenever you need it. I hope it impacts your career and your growth the way it did mine. Here’s to loving and crushing your future as a VP.

#1. Negotiate severance up front.

It is literally a flip of the coin if you will make it past 1.5 years. I know, I know, you are the special flower who can predict “heads” every time, but you won’t control when the coin is flipped.

Thank you Azad Zaman for sharing the average tenure of sales leaders and sales reps. 

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The average is still less than 2 years, so don’t worry aspiring VPs if you keep moving companies. You are awesome. Jack Lazo’s insight reinforces this.

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#2. There is a 99.99% chance you will not vest all your equity. 

Know that when you negotiate pay. Here is what you should ask for:

    1. .5-1% series C or later

    2. 1-2% series A-B

    3. 3-5% Seed

    4. No cliff or 6 months

Amy Volas also makes a great point:

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I’ve included this next one because Jackie Ferro also makes a great point, and I want to call out her comment that moving companies can be viewed negatively. Hold that thought you just had, I’ll get to it in #9.

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#3. The number one reason you will fail is that you will try to do too much yourself.

Enough said. Build a network early. Bring in outside help sooner than you think you should.  You have help if you are looking for it. 

#4. The product will have 3-5x less features/market penetration than what you are promised.

Do the best you can with what you have….it will most likely be less than what you think. 

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#5. You are an amazing and talented person. You are good enough. 

Don’t let any VC or CEO tell you that you aren’t. You are playing a losing game from the moment you step into the role. They are just following a formula that only works 10% of the time anyway…doesn’t make a whole lot of sense but hey….is what it is. 

My salespeople, this is the role many of you are aspiring to. Know this is what it is. 

And no matter what, through all the firings and “it’s mutuals” you are good enough.  You are talented. You do care and are passionate. I got you. 

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#6. The attitude of specific investors on what a Sales Leader should be able to do (of course not yours).

I attended a conference earlier this year – exclusively for Sales VPs.

The VC stood up on a panel and said, to a group of Sales VPs/CROs, “If the product/market isn’t ready or there yet, then that’s on you to figure it out.” 

“Yeah – man you figure it out. You deal with it.” BS. 

It’s not your fault if you can’t “figure it out” at times, you are awesome, my friends – it’s the CEO’s fault for overselling where the product/TAM was to investors, and hey, I don’t blame him or her. At times you have to put some lipstick on it, but this makes the head of Marketing and Sales the most common scapegoats.  

The VC should have said, “It’s up to you to call it out and challenge the board, CTO, and CEO to fix the real problem….and then do the best you can.” 

You aren’t an engineer. You don’t have a magic wand. Do the best you can, and when you hear things like this…tune it out. 

Again – it just is what it is. Just be aware of what really happens as a VP. 

Keep Calm – SOOOOO…. many positives to being a VP of Sales

#7) You will become a millionaire.

If you are a VP of Sales, and you’re not terrible. If you care about the people, and you don’t piss too many people off, you will become a millionaire. You probably won’t generate multi-generational wealth, but you will be successful.

#8) You’re going to get a chance to impact 1000s of people. 

It’s pretty awesome to be able to say that. But you have to realize that the way you’re going to impact these people is by serving them. There is a lot of responsibility that goes into that, but enjoy the impact you’ll make.  Care about people and take this seriously.  

It is the best part of the job and you have to be honest with yourself about your strengths. If you like selling more than leading, it’s not be right role.  You can still make a big impact as an IC don’t worry about having to be a VP. 

#9) The narrative of you leaving a job… it doesn’t really matter

If you get fired or you leave – as long as you’re good at sales, you’re a good person, and you did the right things – you don’t need to stress about it. You’ll reroute, and you’ll be fine. I’ve been fired. 90% of my friends who are VPs of Sales have been fired. Or we “left on mutual terms” which really just means fired. And we’re all fine. You’ll be fine too.

There are many, many positives to being a VP of Sales. A lot of opportunity to touch people and really make an impact. I think that makes a lot of it worth it and you have to go in eyes wide open.


If you have friends or colleagues who are aspiring VPs of Sales, send them this cheat sheet. If you’re a current VP of Sales and have some advice you’d like to add to help out some future VPs, share it below. 

Let me know what you think my friends and please share with your network if you think they will see value. ?


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