Clio (Founded 2008) and Gamma (Founded 2020) Just Raised at $7.5B Combined. Here’s What They Know About AI That You Don’t.
Too much technical data? Too many legacy customers to support? Too many new AI competitors?
I hear you. But stop with the excuses.
Get AI Native — yourself. Clio and Gamma prove you can still win in AI B2B even if you were founded pre-AI:
- AI-native isn’t about your founding date—Clio (2008) and Gamma (2020) both existed before the AI era but made themselves AI-native through intentional transformation
- The fundamental shift: Stop building tools that “support workflows” and start building products that “do the work” (with humans in the loop for judgment)
- TAM expansion opportunity: AI doesn’t just make existing customers more efficient—it can 2-5x your addressable market by making your product accessible to previously underserved segments
- The convergence coming: In every vertical, the boundaries between different types of software are dissolving. The platform with the data and customer relationships has an unfair advantage—if they move fast enough
- Three concrete actions: Stop asking for feature requests and start observing real work; reorganize product thinking around automation; map every workflow as human-only, AI-augmented, or AI-substituted
Legal software Clio just announced a round at $5B valuation. Founded in 2008.
Presentation software Gamma (which we use every day at SaaStr) just raised at $2.5B valuation. Founded in 2020.
What do they have in common?
Both were around before the AI Era. Well before for Clio. Clio started in 2008 as the first cloud-based practice management system for lawyers. Gamma launched in 2020, before ChatGPT changed everything.
And both just closed massive rounds with a common thread running through their announcements: being “AI Native” is critical to winning today.
If you haven’t built AI-native from day one… what’s your excuse?
It’s not really about excuses. It’s about urgency.
The AI Native Advantage Is Real (And the Data Proves It)
Let’s be brutally honest about what “AI Native” means in 2025. It’s not about slapping a chatbot on your product and calling it AI-enhanced. It’s about fundamentally rethinking how your software does work instead of just facilitating work.
Grant Lee from Gamma said it best in his announcement: “Gamma, and our 70 million users, are proof that an AI-native company can disrupt a category everyone assumed was won.”
Think about that for a second. PowerPoint was invented before the first website. Before the Game Boy. Before the Berlin Wall fell. And yet here’s Gamma, founded in 2020, reaching $100M ARR profitably with just 50 people. That’s $2M ARR per employee.
They’re creating 30 million gammas every single month. They’re releasing their API to the general public so you can plug Gamma into wherever work happens. They’re building a full visual storytelling platform that goes far beyond what the incumbents ever imagined.
That’s not iteration. That’s category reinvention.
AI Native Isn’t a Launch Date
When Clio raised their $900M Series F last year, investors asked CEO Jack Newton point blank: “Legal is near the top of the list of industries that’s going to be disrupted by AI. Is this a threat or is this an opportunity for Clio?”
Jack’s answer? It’s a massive opportunity. But only if they fundamentally transform how they think about product development.
Here’s the radical shift Clio made: They stopped listening to what customers said they wanted and started embedding themselves deeply in how law offices actually work. They stopped selling software that supports workflows and started automating entire roles.
“Sarah Tavel wrote a great piece talking about this concept of needing to do the work—we’re selling work rather than software in the age of AI,” Jack told me. “In order to sell that work, you need to think not so much ‘how do I support a personal injury lawyer in keeping on top of their to-do list,’ but ‘how do I help them draft a demand letter completely automatically?'”
That required going deeper than they’d ever gone before. “The job of a product manager, the job of your product organization in general, has radically changed over the last couple years if you want to capitalize on that AI opportunity.”
TAM Expansion Is What “AI Native” Unlocks
Here’s the part that should wake you up: AI isn’t just about making your existing customers more efficient. It’s about expanding your total addressable market by 2-5x.
Jack shared a stat that reframes everything: 77% of legal matters go unresolved with the help of a lawyer. Why? Lawyers are too expensive, too inaccessible, and too overwhelmed.
“AI will dramatically lower the cost of delivering legal services,” Jack explains. “Concurrent with that, the cost of accessing legal services will be dramatically lowered. That, in turn, as it did with textiles and automobiles, the amount of demand and the number of people that can then access those goods is dramatically going to expand.”
The legal market is currently about $1 trillion annually worldwide. Jack believes AI presents an opportunity to double, triple, or quadruple the size of that TAM.
That’s not a defensive AI strategy. That’s offense.
What “Making Yourself AI Native” Actually Looks Like
Clio is mapping legal work into three categories:
- Jobs that humans will do only: Strategic decision-making, client relationships, high-stakes judgment calls
- Jobs that will be augmented with AI: Legal research, document review, case analysis
- Jobs that will be fully substituted with AI: Routine document generation, intake qualification, scheduling, follow-ups
“In the very near future, you’re going to call a law firm and you’re going to speak to what sounds like a human being helping qualify you and see if you’re a fit for the law firm,” Jack predicts. “A lawyer is going to be sitting down with a cup of coffee in their hand in the morning, interviewing potential clients that that AI intake agent has helped set up meetings with.”
On the practice of law side: “Lawyers are going to have their productivity dramatically amplified by agentic AI that can go do legal research for them, that can go draft briefs for them. Lawyers absolutely need to be in the loop here, but they’re going to be able to get a lot more done in a lot less time.”
That’s what AI-native means: Not enhancing your existing workflows, but reimagining what’s possible when entire categories of work can be automated or dramatically amplified.
AI Enables Convergence
Here’s where it gets really interesting. Clio has traditionally been a “business of law” platform—helping law firms run their operations. They stayed in their lane. They didn’t try to build tools for the actual practice of law.
But Jack sees massive convergence ahead, and it’s driven entirely by AI.
“The business of law tools are going to get pulled into the practice of law over time, and similarly, practice of law tools—especially as agentic capabilities start emerging—are going to get pulled into the business of law,” he explains.
Customers are already asking: “Why can’t I draft that document directly within Clio? I’ve got all the data that I need to draft that document in Clio. You just need a few AI-based tools to really help support this.”
Jack’s prediction: “Over the next 2 to 3 years, a massive amount of convergence between the business of law and the practice of law. And there’s a flavor of this pattern happening in many other verticals in SaaS that is going to really dramatically reshape the competitive landscape.”
This pattern is happening in many other verticals.
If you’re in vertical SaaS—whether you’re in construction, healthcare, real estate, logistics, whatever—the boundaries you’ve respected for years are about to dissolve. The companies that own the system of record (like Clio does for legal) have an unfair advantage because they have all the data needed to automate the actual work.
Your Unfair Advantage: The Control Point + Complete Context
If you’re sitting on a system of record—if you’re the control point in your vertical—you have something AI-native startups don’t have: complete context and data gravity.
As Jack explains: “As the control point and as the home to all of that client data, home to all of those workflows, we’ve got an unfair right to win in a lot of these AI-based workflows because we have uniquely broad access to all of that data.”
A thousand AI-native startups are coming for your vertical. They’re fast, they’re smart, and they’re building impressive point solutions. But they don’t have what you have: years of customer data, workflow history, integration partnerships, and customer trust.
The question is whether you’ll use that advantage before it expires.
Three Things You Need to Do This Quarter
If you’re a SaaS founder or product leader reading this and feeling the urgency, here’s what AI-native actually requires:
1. Stop asking customers what features they want. Start observing how they actually work.
Clio realized they needed to embed themselves in law offices, not just survey lawyers. You need ethnographic product research, not feature requests. Watch your users work. Identify the tasks they spend hours on that AI could do in seconds.
2. Reorganize your product thinking around “doing the work” not “supporting the workflow.”
This is the hardest mental shift. Your product team is probably still thinking about building better tools for users to do their jobs. You need to think about how to do their jobs for them—with them in the loop for judgment and oversight, but with AI handling the heavy lifting.
3. Map out which jobs will be augmented vs. substituted, and build accordingly.
Not everything should be fully automated. Strategic thinking, relationship building, and high-stakes decision-making still need humans. But intake, qualification, document generation, research, analysis, scheduling, and follow-up? Those are all candidates for full or partial automation.
Make a spreadsheet. List every major workflow in your product. Mark each one as “human only,” “AI-augmented,” or “AI-substituted.” Then build the roadmap that gets you there.
It’s Not Too Late, But the Clock Is Running
If 2008-era Clio and 2020-era Gamma can make themselves AI-native and raise at multi-billion dollar valuations, what’s stopping you?
The answer can’t be “we weren’t born AI-native.”
Clio has 1,500 employees and 17 years of technical debt. They built their entire platform before anyone knew what a transformer model was. And yet they’re making the shift because they have to.
You can too. But you have to start now.
Because here’s the uncomfortable truth: Your customers are already using ChatGPT, Claude, and Gemini to do work your product should be doing for them. They’re copying data out of your platform, pasting it into AI tools, and getting answers or outputs they can’t get inside your product.
Every time they do that, they’re training themselves to see your product as a database, not a solution.
AI-native wins today not because of when you were founded, but because of how you’re thinking about the work your software does.
PowerPoint was invented before the Berlin Wall fell. That didn’t stop Gamma from reinventing the category with AI at the core.
Clio was founded in 2008. That didn’t stop them from completely.
