Ep. 160 - AI Is Rewriting the SaaS Playbook—Are You Ready?

04/04/25 • 38 min

SaaS Backwards - Reverse Engineering SaaS Success

Guests: Ken Lempit, James Ollerenshaw, & Rob Curtis

AI is transforming SaaS—but not in the way most leaders think.

Forget the headlines claiming "SaaS is dead." The real shift isn't just in tools—it's in how fast software is built, marketed, and bought.

In this episode, Rob Curtis (VC-backed founder), Ken Lempit (SaaS GTM strategist), and James Ollerenshaw (AI advisor) break down what AI means for the future of SaaS—and why B2B CROs and CMOs need to rethink their strategy now or risk falling behind.

From the death of mid-market software to the rise of agentic AI, they map out how SaaS leaders can adapt, differentiate, and thrive in this new reality.

Key Takeaways:

Agentic AI is here: Build for agents, not just users.
The middle is collapsing: Niche depth and data win.
Ideas now beat execution: Speed favors bold builders.
Risk fuels innovation: GTM teams lead AI adoption.
Data is your moat: Structured models drive defensibility.

Ken, Rob, and James offer B2B SaaS leaders a high-level yet practical view of what’s next—and what it’ll take to win in an AI-native world. If you’re a CRO or CMO thinking about survival and scale in 2025, this episode is your blueprint.

Plus, don’t miss:

👉 Rob Curtis’s AI Venture Studio – StandUp Hiro, where he’s building AI-native tools at lightning speed

👉 Rob’s Substack – Future Work, where he shares front-line insights on building in the agentic age

👉 This Crunchbase article on why VCs are betting on Human x AI teams over foundational models

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Guests: Ken Lempit, James Ollerenshaw, & Rob Curtis

AI is transforming SaaS—but not in the way most leaders think.

Forget the headlines claiming "SaaS is dead." The real shift isn't just in tools—it's in how fast software is built, marketed, and bought.

From the death of mid-market software to the rise of agentic AI, they map out how SaaS leaders can adapt, differentiate, and thrive in this new reality.

Key Takeaways:

Agentic AI is here: Build for agents, not just users.
The middle is collapsing: Niche depth and data win.
Ideas now beat execution: Speed favors bold builders.
Risk fuels innovation: GTM teams lead AI adoption.
Data is your moat: Structured models drive defensibility.

Plus, don’t miss:

👉 Rob Curtis’s AI Venture Studio – StandUp Hiro, where he’s building AI-native tools at lightning speed

👉 Rob’s Substack – Future Work, where he shares front-line insights on building in the agentic age

👉 This Crunchbase article on why VCs are betting on Human x AI teams over foundational models

---
Not Getting Enough Demos?

Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

Previous Episode

Ep. 159 - Why Full-Cycle Reps Are Beating Your SDRs

Guest: Guy Rubin, Founder & CEO at Ebsta

Most B2B SaaS leaders know their top performers carry the team, but few understand why the performance gap keeps widening.

The reality is that just 14% of reps are now responsible for 80% of revenue, and the gap between A-players and everyone else has grown to 11x. Fixing this isn’t about more training or new tools—it’s about creating consistent, data-driven sales execution across the entire go-to-market team.

In this episode, Guy Rubin, Founder & CEO of Ebsta, shares insights from the 2025 B2B GTM Benchmark Report (in partnership with Pavilion) and explains how SaaS companies can close the performance gap, improve forecast accuracy, and drive revenue by making data and behavior work together.

Key Takeaways:

Top Performers Win with Consistency: The biggest gap isn’t talent—it’s execution at every stage of the funnel.
AI Enables Better Selling, Not More Noise: When AI is used to extract insights, not automate spam, it becomes a game-changer.
Full-Cycle Reps Are Back: 45% of companies are ditching the SDR model in favor of holistic sales ownership.
Engagement Drives Forecast Accuracy: Momentum scoring predicts risk before it’s too late to course-correct.
Success = Process + Behavior + Data: Sales isn’t just about gut feel anymore—it’s finally becoming data-driven.

Guy offers CROs and CMOs a blueprint to scale what works, eliminate what doesn’t, and win more consistently—making this episode a must-listen.

---
Not Getting Enough Demos?

Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

Next Episode

Ep. 161 - Is User-Based Pricing Dead? How AI Is Reshaping SaaS Monetization

Guest: James D. Wilton, Founder & Managing Partner of Monevate

The advent of AI is forcing a complete rethink of traditional SaaS pricing—particularly the long-standing dominance of user-based pricing.

In this episode, pricing strategist James Wilton explains why AI-native products are undermining the foundations of per-seat pricing models.

Unlike traditional SaaS, where users are the proxy for value, AI tools often perform tasks autonomously, disconnecting cost from usage in unpredictable ways.

As a result, the most value-aligned and sustainable pricing approach for AI-powered platforms is shifting toward usage-based models.

Wilton argues: "If you’re still defaulting to user-based pricing, you’d better be ready to defend it."

📌 Other Takeaways:

Misaligned Incentives in AI Pricing
With AI, the metric that drives cost (compute) is often not the same as the metric that reflects customer value—creating tension between profitability and value-based pricing.
The Rise of Usage-Based Pricing
As automation and AI reduce the need for additional users, user-based pricing loses its relevance. Usage-based models offer better alignment with customer value and revenue scalability.
Customer Expectations Are Changing
Enterprises prioritize cost predictability. Even in AI-native environments, buyers want fixed pricing or capped usage tiers to maintain budget certainty.
Real-World Example: Help Scout’s Pivot
Wilton shares a case study on Help Scout’s move from per-user to “contacts helped” pricing. The shift improved customer satisfaction, better aligned with value delivered, and even offered greater revenue predictability.

📚 James Wilton’s Book:
Capturing Value: The Definitive Guide to Transforming SaaS Pricing
Get the blueprint for designing pricing that drives both growth and profitability without shortchanging strategy.

---
Not Getting Enough Demos?

Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.

SaaS Backwards - Reverse Engineering SaaS Success - Ep. 160 - AI Is Rewriting the SaaS Playbook—Are You Ready?

Transcript

Ken: Welcome to a special edition of the SaaS backwards podcast, where we explore how SaaS go to market and leadership teams are driving revenue and profitability in their businesses. In this episode, we're kicking off a special series. On the impact of artificial intelligence on the SaaS industry.

What our elite panelists, including yours truly, think it means and will mean for sellers and buyers of enterprise and departmental software solutions.

We'll be looking beyond. Go to mar