Inc - Is Your VP Too Hard to Work With?

So we’ve talked a bit about high performing but toxic employees recently, and that sometimes you have to tolerate one, but not more than one, and not forever.

A different but related topic is The Hard to Work With VP.

The VP that’s smart, gets stuff done but:

• Constantly argues; and/or
• Does things they’re told not to do; and/or
• Breaks rules; and/or
• Creates lots of issues with other VPs
• Etc. Etc.

You’ll probably end up with one or two.  And to some extent, it’s OK.  Your job as CEO and founders is to backfill the weak areas of your VPs.  And to give them the runway to grow and improve as leaders.

And a little argument, some internal friction, etc. can be good.  You don’t want groupthink, and you want the best of your team challenging each other to do even better.  Complacency is a real risk once you start to scale.

So how much drama, how many internal issues, how many broken rules do you put up with — for an otherwise high performing VP?

My learning: 2 hours a week of your time and mental energy.  That’s the max.

I think some of my biggest mistakes, at the time I made them, I had to make them to survive. Still, they were terrible mistakes 

My list:

• Launching too early. In both my start-ups, I launched too early. We almost always launch a bit too early, but I pushed too hard and the products in both cases needed another 3–4 months in the oven. I still make the same mistake today, the difference is I am better at mitigating the risk. The advantage is it does push the team … maybe too hard, but it works. My learning: Launching early is OK if you can afford to stumble a bit. It’s too risky if it’s Lights Out if it doesn’t work.
• Trying to hire a “rockstar” too early. I kept making this mistake, and almost all founders do as well. In my first start-up, I hired the top COO in the world. But in the end, he wasn’t ready to join something too small. He backed out after signing the offer letter. I’ve made the same mistake again since. My learning: hiring a “rockstar” super early is OK — as long as you don’t count on them being a magician. Assume they may not work out, and maybe sure you can thrive if they don’t.
• Moving on from founder conflict better, and more quickly. I keep also making this mistake. I hate founder conflict, and hate churn on the team. But the time often comes when founder conflict just can’t be resolved. The reason is always the same: you both just don’t have the same vision, goals — and commitment. Still, sometimes it’s a risk you just have to take. My learning: you know when a co-founder is a risky hire. And plan around that. Try harder to make it work. Communicate more. Apologize. Play to their strengths. But when it really can’t work — get zen, and try to just leverage the best of what they have built into something new. Don’t let it get under your skin. You knew it was risky.

All these mistakes almost killed me. Yet, without them I would have failed.

The fifth edition of SaaStr Europa will feature 2.5 days, and 3,500 B2B/ SaaS Founders, Executives and Investors, coming together to share their learning in the heart of London. 

We’ll once again take over the entire Tobacco Docks for SaaStr Europa 2024, 4-5 of June and bringing the best in SaaS with us. Use our exclusive newsletter code for a discount on early bird tickets.

Welcome to Part Two of SaaStr founder and CEO Jason Lemkin’s Ask Me Anything session at this year’s SaaStr Annual.

Jason re-takes the stage in Part 2 of the series to answer questions about the right time is to invest in a new product line, building vertical vs. horizontal, multiples in 2024, and much more. 

Building and scaling a startup isn’t for the faint of heart and often comes with many ups and downs that SaaS veterans have experience in. 

So, let’s jump right into Part Two. 

Co-founder and CEO at Greenhouse, Daniel Chait, sits down with SaaStr CEO and Founder Jason Lemkin to share what’s new at Greenhouse, a successful recruiting software company at $200M in ARR today. 

When Greenhouse started, it was at a time when the market was growing up, and there weren’t any playbooks. You could do vanilla 101 SaaS practices and succeed. 

Could something like the Greenhouse of 2015 even make it to market today? 

Who knows. Getting off the ground is one thing — an easy pitch of being an HR tech startup focused on improving hiring. 

But today, it’s not that easy anymore. 

Ah, who should Customer Success report to.

It’s not super simple.

There are generally 3 options in the early and middle days:

• CEO.
• VP of Sales (once you have one) and/or later, CRO once you add one.
• VP of Something Else. Finance sometimes. Product sometimes. The other “business” co-founder.

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