SaaS Backwards - Reverse Engineering SaaS Success

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

11 snips

Apr 4, 2025

Guest

James Ollerenshaw

Guest

Rob Curtis

Rob Curtis, a fintech entrepreneur with over $25 million raised for his AI-native apps, joins AI advisor James Ollerenshaw, who boasts a decade of experience in the field. They discuss how AI is reshaping the SaaS landscape, emphasizing that agility and niche specialization are vital for success. The conversation highlights the rise of agentic AI, the importance of speed over traditional execution, and how data can serve as a competitive moat. Leaders must rethink strategies or risk being outpaced in this rapidly evolving environment.

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INSIGHT

SaaS Market Hollowing Out

The SaaS industry is predicted to experience a "hollowing out" effect.
Mid-market software will struggle, while niche and enterprise solutions thrive.

INSIGHT

Enterprise Buyer Behavior

Enterprise buyers are cautious about replacing established systems.
Disruption will likely occur faster in less regulated sectors like marketing.

INSIGHT

Data as a Moat

A strong data model is crucial for SaaS longevity and defensibility in the age of AI.
Data becomes a key differentiator as AI can leverage it for insights and automation.

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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.

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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