So the other day we left a vendor we’d used for years.  Without telling us, or asking our consent, over the years they’d raised our pricing from $300 a month to $1000 a month. For the same usage.

We moved to another vendor really for non-economic reasons. They’d never once checked in with us until we cancelled.

They then offered to match any pricing, or to move us to a $199 /month tier we didn’t even know about.

Is leaving, or threatening to leave, the only way to get a decent deal at renewal time these days?

I honestly think so.

It’s at least something to reflect on as leaders. We now dread any call with Customer Success or anyone we don’t know at our SaaS vendors. They are always about getting us to pay more. They are never about making us more successful.

Back in the day, as a SaaS CEO, I didn’t allow anyone in sales to be involved in renewals. I had finance handle it, because I thought 98 times out of 100, that took any pressure out of it.  I found that worked.  Upsells IMHO shouldn’t happen at renewal time, a time of stress and pressure. They should happen organically by doing a great job and introducing new products.

Maybe I’m old fashioned.

But at least reflect on if your renewal behavior is leading to inadvertent churn.

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Want to know what it really takes to go public today?

Meritech Capital’s Alex Clayton and Cathy Choi came to SaaStr Annual to give us the answers — and real data.  They’ve helped guide dozens of companies through successful IPOs over the past 25 years.

First, let’s address a common misconception: while many founders dream of going public, the reality is that only about 20 SaaS companies manage to IPO each year. That’s a pretty exclusive club! But what makes these companies special enough to make the cut?

So in the earlier days especially, you’ll be tempted to lean on the sales team to do more than just … sell.  Especially, more after they get an e-signature.  Especially because the first 1-2 successful reps you hire will often be a bit of a product expert, and be great at really understanding customer problems.

So you’ll be tempted to have your sales team … do more than just sell:

• Have them do customer success, and manage the account
• Have them do some support, since the customers will reach out to them
• Have them do onboarding, since that’s critical to make the sale actually work out
• Sometimes, have them do renewals, since they know the account already
• To in general, be the POC after the deal is done
• In other words, to own more of the lifecycle of the customer. Not just abandon them the moment a deal is signed.

This makes logical sense as founders. Concentrate the customer experience in the teammate closest to the customer needs.

It has some positives, the more you ask sales to do. Sales almost always complains if there’s no commission check this week coming, but owning more helps them, too.

But it’s a trade-off. You want your sellers selling for the most part, period.

This edition of the SaaStr Weekly is sponsored in part by Stripe

We've partnered with Stripe to give you access to the internet economy conference. Stripe Sessions brings together the payments and financial technology community to share ideas that drive progress.

Over the past 10+ years, the SaaS community has blown us away with your energy and passion, and has been the driving force in helping us expand from our humble roots of a few hundred Founders at our first meet-up and 1,000 or so at the first SaaStr Annual in 2015.

Fast forward to 2025 and we’ve had over 3,200 VCs who have attended SaaStr Annuals over the years(!). At least 800 every year!

It if’s that bad — it’s just not going to work.

The issue isn’t so much that he’s a complete jerk. Maybe he is, maybe he isn’t, or most likely, it’s somewhere in the middle. It’s that you think he is.

He’s thus clearly already driving you so nuts that you have a dysfunctional founder team.

This is usually unfixable — if it’s gotten this bad. You may be wrong, he may be right, who knows. And in other cases, people are OK working with jerks. Sometimes I am OK with it, if their heart is in the right place and their role is constrained.

So there’s lot of debate on social media of just how big you need to IPO in SaaS and Cloud these days. All 4 of the IPOs since 2021 were at $500m+ ARR: Klaviyo, Rubrik, OneStream and Sailpoint.

But you can IPO at lower levels. It’s just, if nothing else, it’s much tougher to get attention if you do. Many institutional investors avoid IPOs at less than a $3 Billion valuation to avoid illiquidity issues.

And so small IPOs can happen, but they are tougher in many ways.  Similarweb is one good example. They IPO’d at $190m ARR and today are at:

• $260m ARR
• Growing 16%
• 112% NRR
• 11% Free Cash Flow Margins
• And trading at $841m … or about 3.2x ARR
• Today it’s worth half of what it was at IPO in 2021 ($1.6 Billion)

$841,000,000 is a big success by any standard! But … it’s trading at just 3.2x ARR and is growing at sub 20% rate at that scale.  And so the  markets don’t love it.

It’s also a reminder that being more efficient alone isn’t enough. The markets want efficient growth, but they value growth more than efficiency. At least 2x more. At least.

So many people are producing B2B content these days, let me just give my #1 bit of advice.

If you think it’s great, it may not perform that well. You’ll see. But if you don’t think it’s great, it will bomb.

Some of the best of our 1000s and 1000s of top speakers, blog posts, podcasts, etc. at SaaStr over the year haven’t gotten the attention I would have hoped. Some more obscure start-ups and even public companies … folks just don’t engage with as much as they should.

Sometimes I push hard. When we did the first interview ever with Peter Gassner, CEO of Veeva, folks didn’t totally get vertical SaaS. But it was an A++ discussion on one had done before. We pushed and pushed and over the years so many have learned from it. Pushing can help.

But a dud? A dud just never performs, no matter how strong the brand even. If you know it just not a great post, or interview, just put it away. Even today, Harry Stebbings still doesn’t publish a number of interviews. In the early days, it was a pretty high percent.

For SaaStr Annual, every year we let a few sessions in that I know are duds, but we do them as favors, or because the company is well known, but the content is terrible. They always bomb. I’m 100% right here.

A few years ago, 2 of my favorite, top-tier well-known CEOs came to SaaStr. The best of the best. But the topic was way too obscure and not relevant to the audience.  I asked them repeatedly not to do it, but the team decided to give it a pass.  And … it was the worst attended of 300+ sessions. One of the CEOs yelled at me.  It was a train wreck, and I knew it was coming before the trains even left the station.

If you want to do more content, great. Do it.

Just when you know it’s not great — put that piece of content back in the can. Take a pause and find a piece of content that you truly believe it. The odds are much higher it will have an impact.

This edition of the SaaStr Weekly is sponsored in part by Prismatic

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I did a podcast with Kyle Norton CRO of Owner.com the other day. One of the themes is how many VPs of Sales and CROs think CEOs and Boards and VCs are essentially out to get them. That the goal is to fire them 7-8 months in when they miss an impossible plan. We see this all over LinkedIn, in fact.

Does this end up happening sometimes? Yes

Does any founder I know >want< to fire a VP of Sales that is performing, or even just coming close?

Heck No. No.

The amount of energy that goes into a VP of Sales search is huge. If often takes the better part of a year, and often after an initial misfire or mishire. Everyone wants that VP of Sales to work. Anyone sane knows starting over will take the better part of the year. Almost no CEO or VC firm has a magic, superstar VP of Sales just waiting to gladly take your job.

What I see today is actually many VPs of Sales often given almost too much time. With “macro impacts” and “the downturn” a built-in excuse for many founders today (as long as you aren’t running out of money), I see many CEOs actually wanting to shield and keep underperforming VPs of Sales. Not fire them. Why? Because they just don’t have a better idea.

In the latest installment of SaaStr Workshop Wednesday (sign up for FREE here), SaaStr CEO and Founder Jason Lemkin did a vibe check into the state of SaaS, AI, venture funding, and the rollercoaster of building and scaling a business in 2025. Here’s what you need to know.

• SaaStr 788: The Real Data on What it Takes to Go Big and Eventually IPO with Meritech Capital

• SaaStr 787: The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr CEO and Founder Jason Lemkin

• SaaStr 786: Going Long: How Procore’s Founder Tooey Courtemanche Built a Billon-Dollar SaaS Empire Over 23 Years

Listen on Apple Podcast, Spotify or Google Podcasts

Never buy a SaaS product owned by Private Equity unless you have to

Only exception: if the founder is still CEO

Why:

- Price increases out of the blue

- Lose any real customer success

- Innovation slows down or even ends

- Support usually terrible

And especially:

- Near Impossible to cancel

5 changes you can make today, to grow faster:

- visit all customers in person > $50k ACV

- have weekly 1-on-1 with VP you don't have one with now

- hire new recruiter + meet 30 new folks for #1 open role

- set burn-rate budget for every month

- cut out toxic folks

© SaaStr 2025

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