The Executive Brand Podcast Clio CEO ($400m ARR) on Moving from “classic” SaaS to AI-native
Jack Newton is the founder and CEO of Clio. He started the company in 2008 in Canada, and has since grown it to over 400,000 customers, 2,000 employees, and $400M+ in ARR. They raised a $500M Series G in 2025.
In this episode, we talk about applying lessons from having navigated the Cloud Era to the AI Era, why the best SaaS companies are moving from selling software to selling work, what 17 years of building in legal tech teaches you about selling technology to skeptical buyers, and much more.
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We discuss:
* Jacks learnings from cloud adoption in 2008 and how they translate to AI adoption today
* The Slack message Jack sent his CTO the day ChatGPT launched
* Why “cool technology is less than half the battle” - and why education and movement-building are the rest
* The Steve Jobs approach to product launches
* How Clio went from a system of record to a system of action, and why every vertical SaaS founder should be thinking about this
* The “Sell Work, Not Software” thesis and how it expanded Clio’s TAM from $20B to $1T
* Why your MAUs dropping might actually be a good sign in the AI era
* Jack’s advice for first-time SaaS / AI founders
* Bonus - How he never missed a single day of running in over 20 years (that’s over 7,000 days in a row)
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Connect with Jack:
LinkedIn: https://www.linkedin.com/in/jackbnewton/
Clio: https://www.clio.com/
The Client-Centered Law Firm by Jack Newton: https://a.co/d/0hrcAvfA
The Hard Thing About Hard Things, Ben Horowitz: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205
The Four Steps to the Epiphany, Steve Blank: https://www.amazon.com/Four-Steps-Epiphany-Steve-Blank/dp/0989200507
Sell Work, Not Software by Sarah Tavel: https://www.sarahtavel.com/p/ai-startups-sell-work-not-software
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Connect with Finn:
LinkedIn: https://www.linkedin.com/in/finnthormeier/
Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/
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My personal takeaways:
* AI is compressing a decade into a year: What took cloud adoption 10 years to achieve in legal is happening in 12 months with AI. And the impact is at least an order of magnitude bigger.
* “Sell work, not software” is the new SaaS playbook: Clio’s TAM went from $20B (software + payments) to $1T (global legal services spend) by shifting from helping manage work to actually doing the work. Every vertical SaaS founder should be asking: what does my “sell work” version look like?
* Education was Clio’s real moat, not the technology. When no one else in legal tech was publishing research or running events, Jack invested in white papers, a conference (ClioCon), keynotes - basically a full-blown education movement to get lawyers comfortable with change. The AI chapter is following the same playbook. He’s touring the country doing live demos of AI features in front of lawyer audiences and showing them what’s possible
* Only talk about what’s shipping today: Jack’s approach (inspired by Steve Jobs) is to never announce future products, only demo what customers can use starting today. Very different to most AI startups who overpromise and underdeliver. He believes, long-term, his approach builds lasting trust when everyone else leans on hype
* Five of Clio’s six acquisitions started as integrations in their app ecosystem. It’s a brilliant acquisition pipeline because you get to see real usage data, real product-market fit, and how well the team integrates before you ever write a check. Hadn’t thought about an app marketplace as a sourcing strategy for M&A, but it makes a lot of sense
* Lower engagement can be a feature, not a bug. If your AI agents are automating work for customers, they might spend LESS time in your app. That breaks every SaaS engagement metric we’ve been taught to optimize for. Jack is actively rethinking what “good” usage looks like when the product’s job is to make itself invisible
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