Inc - The Cloud 100 is Hiring For 7,300 Roles

So layoffs are still happening and it’s harder in many spaces in SaaS.

But don’t let that be too big of an excuse for looking for your next role. Many, many folks in SaaS and Cloud are still growing like a weed.

And because SaaS and Cloud overall is still growing a stunning +20% a year, that means tons of jobs are still being created. Even as the drive for more efficiency is leading to layoffs as well.

We’re T-Minus 30 Days Away from the Biggest SaaS Event of the Year

Can you believe how quickly SaaStr quickly is coming up? Don’t miss this opportunity to rub elbows with some of the most influential leaders in SaaS!

So three of my personal favorite SaaS companies went public, Squarespace, Procore, and UiPath.

Squarespace is a personal favorite (and one we run many SaaStr sites on) because it took a category of software that was a commodity and often a free give-away and made it magical. Procore is a personal favorite because it did vertical SaaS the hard way, with many mid-market deals, and made it a tenacious success.  UiPath is a more recent favorite. My interest there is more technical — how it was able to take a quiet corner of software (scripts, really) and turn it eventually into one of the fastest-growing software companies of all time.

Squarespace is worth about $6 Billion today, UiPath $7 Billion, and Procore $8 Billion.

One thing these very, very different, incredibly successful SaaS companies have in common: it took like forever to get really big. 

If you’re unhappy at work, should you threaten to quit? I think you can do it once.

Once.

If you are truly a top performer, top 10%, folks will react. You may even get a raise. In fact, this is one of the easiest ways to get a raise in a BigCo. HR always save some budget for a top performer that is leaving. You can get a raise you otherwise couldn’t get “out of band” at the time, at least sometimes, in a BigCo. Because HR policies have an exception here.

If you aren’t a top performer, well, at least you’ll find out you aren’t. They’ll say Good Luck! We Understand! Time to Spread Your Wings!

Just don’t do it twice. Don’t say it twice. Don’t even half-say it twice.

Too many folks say it too many times. I know if you’re frustrated, it can feel a bit cathartic to allude to quitting several times.

But if you do, you’ll be taken off the critical path, at least in a startup.

No one can really count on anyone that says twice they may leave. They’ll move on to find a replacement. You sort of have to.

Year after year, 100s and 100s of VCs show up to SaaStr Annual locked and loaded, term sheets in hands, on the hunt for soon-to-be Unicorns to add to their portfolios.

From the Founding Partners, Managing Directors and big name SaaS VCs who grace the stage. to the firms that send over a dozen of their Partners and Associates — everyone who invests in SaaS has a presence at SaaStr Annual.

We also see the top private equity firms registering early, and the list of publicly traded companies sending Corporate Development teams is at least 2Xing year over year.

Whether you’re in it for the long haul and need cash to scale, or you’re looking for a speedy exit — or even if your dream is to become part of something bigger, where you can watch your product live on as part of a legacy brand — the folks who can make it happen will be here. And they want to meet YOU.

So take the time to update your LinkedIn, spruce up your pitch deck, and ask your mentors to help you perfect your pitch.

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. 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.

A little ways back we put out a call on Twitter and LinkedIn on folks’ top tip to take friction out of their sales processes. I put together an excerpt video here of a few of my thoughts …

Even better, we got great #1 top ideas from everyone from the ex-GM of Shopify Plus to the ex-CRO at Brex and the CROs of Grafana Labs and Rippling. I think it would be a tremendous exercise to share these ideas with your team and see what folks think they should change / implement at your startup.

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