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AI, Sales + GTM in 2025/2026: This Changes Everything with Jason Lemkin and Owner CRO Kyle Norton

By Jason Lemkin
Monday, May 30, 2025 | Artificial Intelligence (AI), SaaStr.Ai

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today.

And where it will be very soon.

The AI-Native CRO: How Revenue Leaders Must Evolve or Risk Obsolescence.

AI, SALES + GTM

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.

EARLY BIRD ENDS TONIGHT

The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

By Jason Lemkin
Monday, May 26, 2025 | Blog Posts

The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

We’ve already seen something happen in support. You can’t automate 100% of support with AI yet. At least, not reliably. But you can automate 30%-40% of support for real … with top 10% CSAT.

So what does that mean for inside sales?

THE 2026 SALES TEAM

In The Age of AI, Onboarding and Time-to-Value Should Be The #1 Goal for Customer Success

By Jason Lemkin
Tuesday, May 27, 2025 | Artificial Intelligence (AI), SaaStr.AiTHE 2026 SALES TEAM

So we’ve been proponents of customer success at SaaStr since the earliest days, since our first SaaStr posts in 2012. The magic of high NRR and a strong CS team was something we were preaching and doing deep dives on since well before it was well understood.

Especially the power of it leading to second order revenue, from upgrades to referrals to word of mouth and more.

But the past few years, since the 2022 slowdown, we’ve grown concerned. Customer Success has in many cases turned into a weaponized arm of sales, and has stopped being the champion of the customer. Most of our own CS experiences at SaaStr and QBRs have been terrible the past 24 months or so. Just disguised upsells, with no one on the call to actually help us:

But AI is changing everything. It changed support first, and now its starting to change sales and customer success. And it will make things better.

But one area where humans can bridge a lot of gaps on is onboarding and time to value. Especially as AI takes over more and more of the sales process.

No matter what else AI takes over, humans can always be the gap fillers here. So for me, today, now in the age of AI, onboarding is the #1 goal for your CS team because it’s the foundation of everything else in Customer Success.

If onboarding is broken, it creates a ripple effect—customers don’t adopt the product fully, they don’t see value quickly, and they’re far more likely to churn. It’s like trying to build a house on a shaky foundation. You can’t fix churn or improve NRR if customers never get properly onboarded in the first place.

THE 2026 SALES TEAM

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Perplexity’s CBO: Speed is The New Moat in AI Sales

By Jason Lemkin
Sunday, May 25, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Perplexity’s CBO: Speed is The New Moat in AI Sales

Perplexity’s CBO Dmitry Shevelenko joined Sam Blond ex-CEO of Brex at 2025 SaaStr + AI Summit for a deep dive on AI and Sales. More on the full session coming soon but this deep dive on being prepared for meeting prospects in the Age of AI was super interesting.

“Every question you would typically ask during a discovery call should now be asked of AI before the meeting.”The 90-Minute Meeting Prep is Dead

Here’s a hard truth every CRO, VP of Sales, AE and founder needs to hear: You have no excuse to not be moving faster.

While you’re spending 2+ hours researching prospects, reading through LinkedIn profiles, and manually preparing for sales calls, your competitors are using AI to compress that same preparation into minutes. The result? They’re having more conversations, closing deals faster, and scaling their businesses while you’re still stuck in research mode.

Perplexity’s CBO shared how AI is revolutionizing meeting preparation—and it’s not just about efficiency. It’s about unlocking what he calls “superpowers” that transform how founders approach every customer interaction.

THE NEW MOAT

Ask SaaStr's AI

Talk to SaaStr's digital mind built on years of SaaStr content, insights, and lessons learned from scaling SaaS companies. Think of it as a walking, talking SaaStr encyclopedia—but with a conversational twist. Its been trained on thousands of SaaStr blog posts, podcasts, event sessions, and personal anecdotes from Jason’s journey as a founder, CEO, and investor.

It can help you tackle a wide range of challenges, from scaling your SaaS business to navigating fundraising, building a team, or even finding product-market fit.

Here’s what our AI can help with:

Scaling SaaS Companies: Whether you’re trying to get from $1M to $10M ARR or $10M to $100M ARR, I can share strategies, benchmarks, and tactics that have worked for other SaaS founders. From hiring your first VP of Sales to optimizing your go-to-market motion, I’ve got you covered.

Fundraising Advice: Need help with your pitch deck? Wondering how to approach VCs or what metrics you need to raise your next round? I can provide actionable advice based on Jason’s experience as a founder and investor.

Building Teams: From hiring your first management team to scaling your sales and customer success teams, I can help you avoid common mistakes and build a team that can scale with your business.

Finding Product-Market Fit: If you’re still in the early stages, I can share insights on how to brute-force your way to product-market fit, based on Jason’s experience with EchoSign and other SaaS companies.

Tactical SaaS Advice: Whether it’s improving your NRR, reducing churn, or figuring out how to price your product, I can share specific, actionable advice to help you hit your goals.

SaaS Metrics and Benchmarks: Need to know what good looks like at your stage? I can share benchmarks for growth, burn rates, CAC, LTV, and more.

M\&A and Exits: If you’re thinking about selling your company or acquiring another, I can share lessons from Jason’s experience with EchoSign’s acquisition by Adobe and Salesforce’s M\&A strategy.

Community and Networking: SaaStr is all about community, and I can point you to resources, events, and connections that can help you learn from others who’ve been in your shoes.

If you’re building or scaling a SaaS company, our AI is here to help you navigate the journey with less stress and more success.

ASK OUR AI

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