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The Great AI Reset: It’s Time to Refound Your Start-Up. Now.

By Jason Lemkin
Monday, May 19, 2025 | Blog Posts

The Great AI Reset: It’s Time to Refound Your Start-Up. Now.

Is your B2B startup now part of the past … because it was founded before 2023? Maybe. Be honest.

Has growth slowed while new AI entrants in your space are growting at epic rates?

No one’s coming to save you. But … but … it’s too late to refound your start-up in the Age of AI. It’s not too late.

IT'S TIME TO REFOUND YOUR STARTUP

Can't Wait to See You Again Next May

SaaStr Annual 2025 was an incredible gathering of SaaS and AI leaders, and it was amazing to see everyone come together to share, scale, and learn. From groundbreaking AI demos to tactical sessions with some of the brightest minds in SaaS + AI, this year’s event truly raised the bar.

We’ll Be Back in May 2026:

For us, moving SaaStr Annual back to May has been about returning to our roots. The earlier timing allows us to focus on what matters most: creating the ultimate environment for learning, networking, and scaling. We had such positive feedback on-site surrounding May that we'll be back at the same time next year.

SEE YOU NEXT MAY

Dear SaaStr: We’re Thinking of Bringing in an Outside CEO to Help Us Scale. How Much Should We Pay Them?

By Jason Lemkin
Monday, May 19, 2025 | Q&A

First, before you go down this path — are you sure? 90% of SaaS companies that IPO … IPO with the founder as CEO. That data here.

Are you sure the better answer isn’t to go find a great VP or two to help you scale?

Usually getting more seasoned help is a better answer. Usually an outside CEO doesn’t magically solve your growth or scaling problems.

If you are going to do it anyway, it is big move, and structuring their compensation correctly is critical to aligning incentives and ensuring they’re motivated to drive growth. Here’s how I’d approach it:

Base Salary: For an outside CEO, the typical base salary in a startup post-Series A or Series B is around $250k-$400k, depending on the stage and the size of the company. If you’re further along—say $15M-$20M in ARR—this could go up to $500k OTE (on-target earnings, including bonuses). The salary should be competitive enough to attract top talent but not excessive to the point it drains resources.
Equity: Equity is the real incentive for a CEO to succeed. Most outside CEOs will expect 6-8% equity in the company, possibly 4-5% if you’re mid-stage. This equity should vest over four years, with a one-year cliff, to ensure they’re committed for the long haul. In some cases, they may negotiate anti-dilution protection if a fundraising round is imminent.
Performance bonuses: Tie bonuses to clear, measurable goals—ARR growth, profitability, or other key metrics. For example, you could offer a bonus structure where the CEO earns an additional $50k-$100k for hitting specific milestones, like doubling ARR or achieving a certain NRR (Net Revenue Retention) target.
Stock Option Pool Expansion: Be prepared for the new CEO to request an expansion of the stock option pool to bring in their own team. This could mean allocating an additional 8-10% of equity for new hires, which is often necessary to attract top-tier talent.
Alignment with Company Stage: If you’re early-stage, cash compensation should be modest, with equity being the primary driver. If you’re later-stage and cash flow positive, you can afford to pay more to de-stress the CEO’s life. The last thing you want is a CEO distracted by personal financial concerns.

Ultimately, the goal is to create a package that rewards the CEO for driving exponential growth and aligns their financial success with the company’s success. Make sure the equity package is meaningful enough to motivate them to think like an owner, not just an employee. If you structure it right, the CEO will be incentivized to grow the company aggressively while keeping long-term sustainability in mind.

But make sure this change … really makes sense. An outside CEO will never know the product, the problems, or in most cases, truly care the same way as a founder CEO.

HOW MUCH TO PAY OUTSIDE CEO

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Are You Fundable Today? Just Ask Your Existing Investors. Just Ask Them.

By Jason Lemkin
Sunday, May 18, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Are You Fundable Today? Just Ask Your Existing Investors. Just Ask Them.

So Venture Capital is back in force — but not for everyone.

71% of all VCs dollars are going into AI
VC dollars are more and more concentrated into winners at growth stage
Many traditional B2B VCs are now looking for faster growth than even T3D2 today, in the Age of AI

So everything in some ways seems the same in fundraising, but really, is so different.

And what I find is that most founders just don’t know.

They don’t see 100% of the change directly, and they don’t really know for sure if they are fundable or not. Especially when so many of the big rounds on TechCrunch were actually signed and even closed before the Big Change.

ARE YOU FUNDABLE

The Bar Today for a Series B

By Jason Lemkin
Saturday, May 17, 2025 | Blog Posts

Navigating the Funding Gap: Insights from 10,755 US Startups

In the world of SaaS startups, securing Series A funding is an achievement worth celebrating. At least for a day :). It’s a sign you’ve hit Initial Traction.

But each round usually gets harder. Successfully graduating to Series B takes a lot of strong growth and metrics.

The latest data from Carta analyzing 10,755 US Series A startups offers a revealing look at these graduation rates – and there are important lessons for B2B founders to absorb.

THE BAR FOR A SERIES B

Events Work. Events Are Back. But Are They Worth the Big Expense?

By Jason Lemkin
Saturday, May 17, 2025 | Growth, Marketing

Events Work. Events Are Back. But Are They Worth the Big Expense?

Events. They are back.

As marketers and sales leaders struggle to figure out what’s working in GTM in the Age of AI, as SEO and cadences aren’t working like they were … IRL events are back.

They’re real, they’re authentic, and buyers show up to the best ones. Even in the age of ChatGPT.

But are they worth it?

Not just the hard costs, but all the soft costs, too? Especially these days. Haven’t we all moved to a hybrid or distributed world? Can’t we all close $1m deals on Zoom now? Don’t we all just work in the cloud now? Can’t an AI SDR just get me all the leads I need anyway? (ahem).

It took me a long time to have a strong opinion on events (yes, there’s some irony there, given that we put on SaaStr Annual, SaaStr Europa, etc.). In my first start-up, we were hunting big whales — $1m+ deals. There was one big industry event a year. We went. We met both our key partners there, connected with one of our key customers and met a key stakeholder there we hadn’t yet met, and brought back one — (1) — lead. But that lead was worth potentially $1m a year, and was a lead we weren’t doing a great job of otherwise building a relationship with. Six weeks later, we were at their HQ, talking a long term deal.

But once I started doing B2B and dealing with much smaller deal sizes, I wasn’t sure. We did the biggest events in the industry — Dreamforce for “sales”, and SHRM for HR — and they seemed to be worth it. Even though the leads sure took a long time to close.

It probably wasn’t until our 4th Dreamforce, though, when I started to get it. A bunch of bigger customers I’d never met came by to meet us, at our booth in particular. I remember they brought a lot of gripes in particular (maybe happy customers just grab a T-shirt and go). But I took the gripes back, addressed the issues, and never lost those customers. At this same Dreamforce, we also met with a bunch of prospects. One of them was a web leader already in the pipeline but stuck there. They quickly closed the week after meeting at Dreamforce for a nice six-figure deal.

EVENTS ARE BACK

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