The Latest from SaaStr: All Your VPs Really Need to Do is Tilt the Curve

We’ve written a lot on SaaStr on how to increase the odds your first management team is a success.  How to hire a great VP of Sales  What a great VP of sales really does. What a great VP of marketing really does.  When to hire her. How to manage customer success. How to hire a great VP of product. All good stuff.

But as I now work with 24+ scaling SaaS companies, all of whom, all of us, who struggle to build a great management team … I’ve learned to distill it all down to one thing.

Yes, VPs are ultimately about building a team.

About recruiting and helping you scale. About letting you move from micromanager to manager. About this and that.

And some will be stretch VPs, and some seasoned VPs, and some with start-up experience, and some without, and some generalists, and some specialists.

Like many things, my thinking on this has evolved over time. I used to think having co-CEOs was almost always plainly a bad idea.  And clearly, it’s still quite rare.

But now I think maybe it’s only a bad idea when done for the wrong reasons.

The drawbacks of co-CEOs are large and clear:

• No one knows who the boss is. It’s very confusing who makes decisions ultimately.
• High potential for ego issues. Are the founders just kicking the can on a big issue — who’s ultimately the CEO?
• High potential for multiple marching orders. If CEO #1 says do A and CEO #2 says do B, it’s just so confusing, again.

I’ve worked in a 2-founders-are-equal environment, and it is confusing. No doubt. I often wasn’t sure who my boss really was.

But …

It’s also not always clear who the boss is with your parents.

If the co-founders are truly partners, and partners for life (or at least, for decades), and truly have deep respect for each other, and truly want to be co-CEOs (i.e., both are OK with the stresses, too), then it can work.

This edition of the SaaStr Daily is sponsored in part by Infinicept

Learn how to bring payments in-house without taking on extra costs and risks and create a better payment experience.

The challenges businesses face at each growth stage, from a $1M company through $100M and beyond, are quite different. 

Xero’s Global Chief Strategy Officer, Damien Tampling, takes a philosophical look at some aspects and nuances to consider wherever your business is on this journey.

Over the last couple of years, Xero has doubled revenue and operating revenue, tripled annualized monthly recurring revenue, and quadrupled lifetime value. Let’s dive into some of Damien’s top learnings for building a global platform and ecosystem. 

Times are tougher for many now, and the risk of failure can seem more tangible these days.  I haven’t failed yet, but boy every time, I’ve come close.

So I thought I’d update a list of the “little things” I let go, but that I shouldn’t have, that almost killed me/us:

Setting a little too insane of a goal. Crazy goals are good, but I wonder about insane. At Adobe Sign / EchoSign, I said we’d do $2m ARR by the end of Year 1. We ended up at $200k in ARR. Not terrible 1 year from launch, looking back, especially by the standards of the time.

But the team was dejected and broken. One cofounder quit. Another fired another one. I thought we could do it, though. But I should have stress tested that assumption a little more. This cost me one of my cofounders, and some of the engagement of another.

Not paying myself a salary — for a little too long. Once we were in trouble, I stopped taking a salary, and reinvested a bunch of the proceeds from my first start-up to keep us going. That was OK.

But I took it a little too far.

I did it a little too long. This gave me an excuse. To do OK, but not to kill it. After all, I wasn’t taking a salary! Pay yourself once you can afford to. This cost me some of the urgency I needed — once things finally got good!

Communicating with challenging teammates a little too little. I still struggle with how to maintain a constant flow of communication with folks I lack alignment with. I do dailies every day with the folks I’m aligned with, but I tend to shrink away from constant communication with folks I have disalignment with.

This doesn’t work. You have to flip it around. You can save team members, or at least extend their lifetimes, just by communicating better, more often. This cost me several key team members leaving 6–9 months earlier. I would have loved to have had them longer. 

This edition of the SaaStr Daily is sponsored in part by Secureframe

Secureframe makes it easy to get SOC 2 compliant. With guided workflows and one-click integrations, the entire process is automated.

This is a tough and very specific job.

Most sales folks can’t do.

Usually, being the first start-up salesperson is a rewarding, but very tough job:

Your boss has never probably managed a salesperson before. She or he likely won’t know what you are supposed to do 40+ hours a week. Even if they’ve closed the first 10. 20. 100 customers themselves.

Your boss may have strong views on what you should be doing. And their views may be wrong. Whichever founder was doing sales, likely thinks that may be the way to do sales going forward. Which it may well not be.  As the first AE, you have to be smart, agile and flexible.  But you can’t do founder-led sales yourself.  You need a different playbook.

Your boss may think you are very expensive. If the founders are making almost nothing, coming in with a high OTE (“on target earnings”) may make you, on paper at least, the most expensive employee in the company. This can create a lot of pressure to deliver, quickly.

Your boss may have unrealistic ramp expectations. Great salespeople should ramp quickly. But they can’t ramp in a day. This can create tensions, in some situations at least.

You may well not have enough leads to hit quota. It’s too early. Most start-ups below $1m in ARR don’t have enough in-bound, organic leads (say ~50+ qualified leads) a month to keep the first salesperson busy. You’ll have to find a way to get more leads on your own.

We’re just 10 weeks away from SaaStr Europa in London, June 6-7!

As always, we have an amazing agenda for you! Here are just a few of the top SaaS leaders that will be speaking.

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