Hey SaaStr Community,

So backstage at SaaStr Annual this year, and in a number of other conversations since, I’ve had a chance to get a few quiet moments with maybe two dozen top CROs and VPs of Sales.

I’ve asked all of them what’s really on their minds.  

Yes, macro issues come up, and how they have to sell to more stakeholders now, and sales cycles are longer.  But the best long ago adapted.  A tougher selling environment happens, It just is what it is.  The top CROs and VPs of Sales don’t complain about macros. They adapt to them.

But 3 issues have come up again and again, that CROs don’t want to talk about in public.  That they don’t want to be on the record about.  Because they’re triggering, or in conflict with the LinkedIn Vibe.  But they talk about it backstage.

The Top 3 Frustrations of Top CROs Today:

#1.  Sales Folks Just Won’t Go Back To The Office.

This was the #1 concern and complaint I heard from so, so many CROs.  Many although not most CROs are back to the office themselves. And they don’t care where there top performers work anymore. But the rest? 

Almost all of them think it’s critical sales reps outside of the Top 10% work from the office at least 2 days a week, and ideally 3. They also don’t think remote onboarding and training and culture is working well enough in sales. But they’ve thrown up their hands in many cases. 

No matter what the company mandates, folks still won’t come in.

And they see this as the #1 thing impacted sales — that they can have an impact on.  They see it in the numbers.  Folks outside of top performers are just less productive from home, in large part because they’re not trained as well and pushed as much.

The best way to drive sales team performance is to have 1–2 folks on the team just making lots of money from closing lots of deals.

An oldie but a goodie here:

• Yes, sales reps can be a bit lazy.
• Yes, they can blame marketing or competition or whatever for not closing.
• Yes, they can talk a lot about “pipeline” without closing anything.

But … at the end of the day, sales is hard. Sales is a lot of Nos. You have to believe. You have to believe it can be done. And it’s easy to get discouraged.

And when you see a couple of folks ringing the bell every day, making tons of money, and having a good time doing it … that drives the rest of the team.

And over time, it also attracts more top reps to your team.

So rather than figure out how to make the struggling reps better, slow it down.  Figure out how to make 1 or 2 sales reps that are already smart, and closing … be wildly successful.  They blaze that path after that for you, to a significant extent.

So things aren’t all “bad” in SaaS.  Many Cloud leaders stock prices are way, way up in 2023, the Cloud platform leaders have re-accelerated, and leaders like Shopify are having close-to-record years.

But for many startups, the hangover from the Excesses of 2021 is a real and tough one.

And the latest Carta data here supports that. Startups shutting down are up 238% this year — already.

Sending you all Holiday cheer as we hope you'll join us for the biggest SaaStr Annual yet, when we host the 10th SaaStr Annual across more than 40+ acres! 

In 2024, we'll be hosting the biggest SaaS event of the year with 13,000 SaaS Founders, CEOs, Revenue Leaders and VCs with 300+ of the Best Speakers in SaaS, 100+ workshops from the top CROs and revenue leaders, and 1,000's of Braindates and endless opportunities to network and meet in-person.

Register during our Buy More, Save More Holiday Event to save 20% on 1-2 tickets, saving more than $200, or go for a team pack and save 30% on the ticket price.

But hurry - these savings expire at midnight December 15. 

So there’s a quiet SaaS leader you probably haven’t heard of in the financial reporting space that’s doing just fine today. They manage financial reporting, audit, risk and more. Many of you will end up using it as you scale to later stages.  That’s Workiva.

They’ve crossed $600,000,000 in ARR, growing a steady 19%, and are worth a cool $5.5 Billion in today’s world.

That’s a pretty good multiple, so they’re doing something Wall Street likes. Let’s dig in and learn just what.

#1.  5,945 customers, up 7% From 12 Months Ago.

Workiva’s average deal size as you can see is about $100k, and their NRR is 112% with ad-ons.  112% + 8% logo growth = 119% total revenue growth.  That’s not epic customer growth but it gets harder as you approach $1B in ARR.

So discounting is such a surprisingly nuanced and complex topic in SaaS.  While a few leaders like Atlassian do pursue a mostly “no discounts” policy for the most part — that just doesn’t work in practice for 99% of us.

As much as we’d all love to have a No Discounts policy … it’s tough in practice.

First, it’s often impossible to get through many procurement departments without one. Second, many enterprise customers are simply used to them, and feel ripped off without one. And third, it’s a tool to create urgency.  Sort of.  But only when used properly.

So I was curious — how many of you really “hold the line” on those end of month / end of quarter deals?  It turns out, those deadlines are quite so … deadly.

Providing robust integrations is an essential part of any B2B SaaS product strategy. Find out if you are ready for an embedded integration platform.

SaaStr founder and CEO Jason Lemkin chats with Box CEO and Co-Founder Aaron Levie to talk about what’s new at Box, SaaS fatigue, hiring a new COO, operating margins and efficiency, the future of AI, and what to expect for 2024.

Let’s jump into Aaron’s advice, hot takes, and of course, What’s New. 

On How to Go Long in SaaS:

There are a variety of factors involved in keeping the energy up to continue building a business in SaaS. Aaron has been at it with Box for almost 20 years. How does he do it? 

“I’ve never been able to come up with something more exciting than software,” he says.

He believes Enterprise software is the most exciting thing. The consumer side is ten times more stressful because you don’t have recurring revenue, and a single change in the platform can alter the entire dynamics of your business model.  You’re dealing with the whim and mercy of the fickle consumer market. But Box has lucked out with 95% recurring revenue. They get to talk to brand-new businesses in completely different industries all the time. 

Aaron’s advice is to have to have a deep passion for continuously trying to solve new problems for people. That’s the part that will change forever and make this industry interesting.

• SaaStr 706: What's New at Box with Aaron Levie, CEO and Co-Founder of Box and Jason Lemkin, CEO and Founder at SaaStr           

• SaaStr 705: Decoding the 2024 Market: How to Scale from Go-to-Market Through IPO for the Year Ahead with ICONIQ Growth’s General Partner Doug Pepper and Head of Analytics, Christine Edmonds               

• SaaStr 704: CRO Confidential: The Hangover's Over: 5 Ways to Get Your SaaS Revenue Back On Track with Gong's SVP Sales, Jameson Yung, and Sam Blond, Partner at Founders Fund       

Listen on Apple Podcast, Google Podcasts or Spotify

I see about 50% of SaaS founders make a truly terrible VP hire.

Just terrible. Common denominator?

The VP worked somewhere very well-known before, but many stages later. And/or is very well known.

It just blinds everyone. Especially your VCs.

A lot of people just don't really want to work that hard

A lot of the rest blame everyone else for everything

Just not being one of them already gives you an edge

Every Week:

Them: "Hey Jason, I'm looking for a new role" 

Me: "I've got a great idea, great startup, great role for you.

You'll have to do a lot of the work yourself though."

Them: "Ah never mind. I mainly just want to manage people."

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