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The Deadly “AI Slow Roll” in SaaS: It May Cost You Everything

By Jason Lemkin
Monday, May 5, 2025 | Blog Posts

The Deadly “AI Slow Roll” in SaaS: It May Cost You Everything

I’m seeing an alarming trend across the SaaS landscape that’s going to separate winners from losers in the next 18 months: The AI Slow Roll.

You know what I’m talking about:

It’s the VP of Engineering who’s “still evaluating Windsurf and Cursor” but says it’s still a little bit early.
It’s the Product leader confidently declaring AI “isn’t ready for prime time because of hallucinations.”
It’s the CRO insisting that “customers all want to talk to a human” and that “a great sales rep beats AI any day of the week.”

Let me be crystal clear: Change fast or die. At least, watch your business atrophy.

Everyone that’s invested in a wide group of B2B and SaaS companies is seeing this. For the most part, those that haven’t aggressively adopt AI in their products are seeing growth slow. Sometimes, they are seeing a bit uptick in churn. Sometimes, retention is staying up but they are losing deals to new entrants. Whatever it is, it’s a threat if you aren’t ahead of the curve here. And it’s accelerating.

Is your team really doing what you need it to here? If not, you will lose.

This may sound dramatic, and honestly I wasn’t even sure change would come this fast just a few months ago. But now it’s 100% clear.

THE DEADLY "AI SLOW ROLL"

The Top 10 SaaStr 2025 Sessions So Far! OpenAI Head of GTM, HubSpot CEO, Canva CCO, DropBox and Snowflake CEOs!

By Jason Lemkin
Monday, May 5, 2025 | Blog Posts

Ok about 2,000 of you have already picked your 2025 SaaStr Annual + AI Summit sessions so far and here are the top sessions … for now:

1. The New Rules of SaaS Growth: What’s Next for AI, PLG, and Revenue Scale with HubSpot’s CEO
2. From Startup to $10B+: Lessons on Scaling, AI, and the Future of SaaS with Dropbox’s Founder and CEO
3. Kick-off to SaaStr Annual 2025 with SaaStr’s Founder & CEO
4. How AI is Reshaping Enterprise SaaS: Learnings from Box’s CEO & IBM’s GVP of A.I.
5. Embracing AI for Better Marketing Outcomes with Asana’s CMO
6. How to Build Top-Performing Sales Orgs: OpenAI, Slack, Webflow + more
7. Closing AMA with SaaStr’s CEO and Founder Jason Lemkin
8. PLG to Enterprise: Calendly’s CEO + SaaStr AMA
9. Ramp & More: The Journey to $200M ARR+ and AI Strategies
10. Scaling AI-Driven Data Strategies: Snowflake’s CEO + Observe CEO
11. How to Build a Category-Leading Product: Own’s CEO
12. SaaStr & Mayfield AI Demo Pitch Competition LIVE Finale
13. AI for Growth: Building AI-Powered SMBs with Gusto’s CEO & CTO
14. AI and the Bottom Line: Canva’s CCO on Freemium to Retention
15. How AI Is Changing the Sales Ecosystem: Artisan’s CEO

There’s so much more, but always interesting to see who and what you’re most interested in!

SEE YOU THERE

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Dear SaaStr: Why Do Enterprise Customers Insist on Pilots?

By Jason Lemkin
Monday, May 5, 2025 | Q&A

I know your sales team probably hates pilots, because in a sense, it means they have to sell the deal twice. Once for the pilot, and again to convert the pilot for a longer deal. Having an “opt out” clause after a pilot ends helps, but still, it’s a double sale.

But the thing is, net net it might be less work. Because so many enterprise customers won’t buy from new start-ups without a pilot.

They benefit in several ways, especially when it’s structured properly. Here’s how:

Risk Mitigation: Pilots allow customers to test your product in a controlled environment before committing to a full rollout. This reduces the perceived risk of adopting a new solution, especially if they’re replacing an existing system or investing significant resources. Risk reduction is key. You are a new or at least a small vendor, after all.
Proof of Value: A well-executed pilot demonstrates the tangible value your product delivers. It’s not just about proving functionality—it’s about showing measurable outcomes, like increased efficiency, cost savings, or improved workflows. This is critical for building trust and confidence in your solution.
Customization and Fit: Pilots give clients a chance to see how your product fits into their specific workflows and processes. They can identify any gaps or customization needs early on, ensuring a smoother implementation if they decide to move forward .
Internal Buy-In: For enterprise clients, a pilot can help them build internal support for your product. If key stakeholders or end-users see the value during the pilot, it’s much easier for the client to justify the investment to their leadership team.
Hands-On Experience: Pilots provide clients with a hands-on experience of your product. This is especially important for solutions that require behavior or process changes. It helps them understand how your product works in practice, not just in theory.
Faster Decision-Making: A successful pilot can accelerate the sales cycle. Once the client sees the value and gets buy-in from their team, they’re more likely to move forward with a full contract without prolonged deliberation.

You can fight doing paid pilots. Or you can lean in … and get good at them. Do the matter, at least in the earlier days, and more deals will close. For the exact reasons above.

But it is … more work. At least at first. At least for some in your org.

The key to a successful pilot is setting clear success criteria upfront.

Both you and the client need to agree on what success looks like—whether it’s a specific ROI, user adoption rate, or another metric. Without that, the pilot risks becoming an endless evaluation with no clear outcome.

WHY PILOTS?

7 Ways AI Will Change Sales In The Next 12 Months

By Jason Lemkin
Sunday, May 4, 2025 | Blog Posts

7 Ways AI Will Change Sales In The Next 12 Months

AI is going to fundamentally reshape sales over the next 12 months, and we’re already seeing the early signs. It’s already fundamentally remade the contact center and post-sales. And it’s just getting there in sales.

Here’s where I think it’s heading based on 100,000+ conversations already on SaaStr’s own AI, and my experience investing in so many contact center and post-sales leaders:

1. AI Will Join Every Sales Call

Within the next year, AI will become a standard participant in sales calls—not just as a note-taker, but as an active contributor. It’ll know your product cold, answer questions instantly, and eliminate the “I’ll get back to you” moments that kill momentum. This will take sales calls from 10% being great to 95% being great because the AI will always be prepared and accurate.

2. Routine Sales Will Be Handled by AI

For simpler, transactional sales, AI will take over entirely. We’re talking about 25–45% of routine deals being closed by AI alone. Customers will prefer interacting with an AI that knows the product perfectly over a junior rep who needs three days to respond. This is already happening in customer support, and sales is next.

7 WAYS AI WILL CHANGE SALES

10 Awesome Things the Free SaaStr AI Can Do For You, From Reviewing VC Pitches to Drafting Cold Outbound For You

By Jason Lemkin
Saturday, May 3, 2025 | Blog Posts

10 Awesome Things the Free SaaStr AI Can Do For You, From Reviewing VC Pitches to Drafting Cold Outbound For You

So our own SaaStr AI has now logged over 30,000 conversations (!) — and it’s pretty awesome.

You can try it right here below embedded in this post, or just click here.

It can answers tons of questions, from how to hire a VP of Sales and where and whom to meet at SaaStr Annual.

But it can also do some pretty epic things you might not think about.

10 AWESOME THINGS SAASTR AI CAN DO

From 0 to $10m ARR, At What Point Do We Start Hiring and Whom?

By Jason Lemkin
Saturday, May 3, 2025 | Q&A

From 0 to $10M ARR, the hiring roadmap is critical because every hire has a disproportionate impact on your trajectory.

Here’s how I’d break it down:

0 to $1M ARR: Founder-Led Everything

Sales: Founders should lead sales. You need to be in the trenches, hearing objections, refining the pitch, and closing deals. No VP of Sales yet—don’t even think about it. Maybe hire 1-2 scrappy AEs or SDRs to help with lead generation and early sales once you’ve proven it yourself, but you’re the closer at least fo the first 10-20 customers, minimum.
Marketing: Likely no VP of Marketing yet either — unless. You might bring on a growth hacker to help with demand gen, but you’re still figuring out product-market fit. Having said that, if you have a steady stream of leads and customers, you really can’t hire a great VP of Demand Gen / Growth too early. A great one will bring you more qualified leads, even at $10k-$20k MRR, so long as there’s a base of demand to build on.
Customer Success and Support: You can hire 1-2 individual contributors to handle onboarding and support, but it’s still very hands-on. No managers here that don’t do 100% of the work themselves. But one small rule: once you even have 2 big customers, hire someone full-time to make them successful. You’ll run out of time to do that yourself, and the big customers you worked so hard to close will get neglected. You’ll regret that.

$1M to $3M ARR: Build the Foundation

Sales: Once you have 2 reps consistently hitting quota, it’s time to hire your first VP of Sales. This is usually around 1M−1.5M ARR. They’ll help you scale the team from 2 reps to 10+ and build a repeatable sales process.
Marketing: Around $1M ARR or if you find someone strong, earlier, you’re ready for a VP of Demand Gen or Marketing. If they can increase qualified leads by even 20%, they’ll pay for themselves. This hire is often more impactful earlier than you think.
Customer Success: If you’re seeing churn or struggling with renewals, or have larger customers that are high touch, consider hiring a VP of Customer Success around 2M−3M ARR. They’ll focus on driving net revenue retention and building a scalable CS function.

$3M to $10M ARR: Scale the Team

Sales: By now, your VP of Sales should be hiring aggressively. You’ll likely need 10-20 AEs to hit $10M ARR, depending on your deal size and quotas. You’ll also need to start layering in Sales Ops and Sales Enablement as the team grows.
Marketing: Your VP of Marketing should be building out a team, including content marketing, paid acquisition, and events. If you’re targeting SMBs, you might also need a growth hacker to optimize funnels.
Customer Success: As you approach $10M ARR, you’ll need a full CS team to handle onboarding, renewals, retention and upsells. This is also when you might need a dedicated Head of Support if you’re seeing a high volume of tickets. AI can’t do it all.
Engineering: As you approach $10M ARR, it’s often time to hire a VP of Engineering in addition to your co-fouding CTO. Why? Usually in B2B, the workflows just start to get pretty myriad and complex. And the technical debt grows. And the need to do more and more integrations, etc. A lot of stuff someone besides your creative CTO can manage. Even the best CTOs need to get stuff off their plates that someone else can do. The stuff that has been done before.
Product: You really need a hands-on VP of Product by this point in most B2B products. Again, the complexity is just too great for the founders to wing it as head of product themselves.

Key Milestones to Watch

$1M ARR: Hire your first VP of Sales and VP of Marketing.
2M−3M ARR: Bring on a VP of Customer Success especially if you have larger customers and/or churn is an issue.
$5M ARR: Start layering in Sales Ops, Enablement, and more specialized marketing roles.
$10M ARR: You’ll likely have 40-50 employees by now, with a fully built-out sales, marketing, and CS team. A head of Product. And often, a VP of Eng.

The key is to hire just ahead of the curve. If you wait until you’re drowning in leads or churn or bugs, you’ve waited too long.

MORE HERE

Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested?

By Jason Lemkin
Saturday, May 3, 2025 | Leadership, Q&A

Yes, it’s true but …

#1. VCs Are Less Rigid Here Than They Used To Be

If a deal is hot and you have multiple offers, VCs won’t push as hard here as in the past. And many pre-seed rounds on SAFEs etc often don’t even touch the topic of founder equity vesting.

#2. Vesting Protects You More Than the VCs. You are thinking about it wrong.

Vesting protects you. It protects you from co-founders that aren’t as committed as you.

Yes, there is an us vs. them element to VCs. No doubt. VCs think about vesting as a way to protect themselves (not that it really does that), and more specifically, as a way to manage the cap table when folks leave the company.

But as long as you maintain control of your company and don’t give that away to the VCs, the real bummer that can come out of all of this is when your “partner” and “co-founder” flames out in 11 months and takes all their equity with them.

And you’re running the company for 10 more years. For the same number of shares your co-founder that quit on month 11 has.

You’ll really, really. Really. Wish you’d had vesting on those shares.

DO VC'S INVEST WHERE EQUITY IS FULLY VESTED?

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The Deadly AI Slow Roll in SaaS