After selling A Cloud Guru for $2 billion, Sam Kroonenburg briefly stepped away from start-up life. Then came the AI boom – and with advertising start-up Cuttable, he’s already built another $100 million company.
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Fresh off the sale of A Cloud Guru, Sam Kroonenburg found himself, for the first time in years, “remembering how to be human again”.
The cloud education start-up he had built alongside his brother Ryan was acquired by Pluralsight in 2021 for $2 billion, marking one of the largest start-up exits in Australian history.
By then, the Melbourne-founded start-up had grown from a spare-room operation into a company with more than 600 staff and $150 million in annual revenue in just over five years.
“It was a crazy scaling journey,” Kroonenburg says. “It felt like baptism by fire, trying to work out how to build a company at that scale so quickly while still delivering for customers.”
The months that followed looked very different. No longer consumed by the demands of hypergrowth, Kroonenburg suddenly had time to slow down and spend time with his children. But, even away from the noise, a new technological wave was beginning to emerge – one he found increasingly difficult to ignore.
As AI surged into the mainstream, Kroonenburg found himself pulled back toward the same fascination that first got him into software as a teenager.
“I didn’t want to sit the AI wave out because it’s the reason I got into software,” he says. “I’ve been building software businesses since I was 13, so I’ve always been obsessed with creating technology you’d see in sci-fi movies.”
Kroonenburg decided to start another company, this time with a singular focus: building something that could only exist because of artificial intelligence.
“My only criteria was to build a business that simply couldn’t have existed two years earlier,” he says. “I didn’t want to bolt AI onto something existing and make it marginally better. I wanted to build something fundamentally impossible without it.”
In 2023, Kroonenburg teamed up with long-time advertising creative Jack White and hospitality entrepreneur Edward Ring to launch Cuttable, an AI-powered advertising start-up built around that philosophy.
The subscription-based platform helps brands generate, test and scale large volumes of digital advertisements across platforms, including Meta and TikTok, using AI to automate much of the traditionally manual production process behind online marketing campaigns.
“The opportunity came from the collision of two megatrends,” Kroonenburg says “On one side, nearly all advertising spend has shifted online, and platforms like Meta increasingly reward brands that can rapidly test large volumes of ads – something that’s been slow, expensive and labour intensive.”
“On the other side, AI reached a point where it could begin handling creative tasks that previously required teams. There was this huge unmet need in the market, and suddenly there was a technology capable of solving it.”
Rather than simply layering AI onto existing advertising workflows, Kroonenburg says Cuttable spent its early years effectively “incubating” the product, bringing together software engineers and advertising creatives to rethink how campaigns could be built in an AI-native environment.
“AI can generate endless amounts of content, but the real challenge is making something that genuinely feels like the brand behind it.”
Unlike many generative AI tools that rely heavily on prompts, Cuttable trains its systems on a brand’s broader identity, learning everything from its products and audiences to the creative rules that shape how the brand presents itself.
“There are so many unspoken rules that exist inside a brand, and we’ve spent the first two years teaching Cuttable to understand all of that,” Kroonenburg says. “When ads can be generated, tested and optimised in minutes, at a fraction of the traditional cost, the economics of the industry change very quickly.”
Today, Cuttable works with more than 300 brands across Australia and the US, including Frank Body, Brooks Running and Toys R Us. Earlier this year, the company reached a $100 million valuation after raising $16 million across multiple seed rounds by investors including Airtree, Square Peg Capital and Rampersand.
“Raising money was definitely easier this time around than it was with the first company,” Kroonenburg says. “It turns out building a $2 billion business gives you a bit of a leg up when it comes to raising capital.”
Despite the company’s rapid growth, Kroonenburg says one of the biggest lessons he carried over from A Cloud Guru was the importance of staying intentionally lean. Cuttable currently employs around 35 people, a figure Kroonenburg believes is increasingly viable for high-growth software companies operating in the AI era.
“Once companies get too big, layers of leadership become disconnected from execution making it hard to scale,” he says. “In an AI world, you just don’t need to scale headcount in the same way.”
Instead, Kroonenburg says much of the company’s internal workflow is already AI-driven, with staff increasingly focused on directing systems rather than manually completing tasks themselves.
“We have very few humans doing the grunt work,” he says. “Our people are orchestrating AI systems to do the work, which gives us a huge leverage.”
With its New York office now up and running, Kroonenburg says Cuttable is firmly set on expanding its presence in the US market, a mindset shaped heavily by his experience scaling A Cloud Guru internationally from Australia.
“I’ve always been a strong believer that you shouldn’t spend years building a business in Australia and only think about going global later,” he says. “You need to build with a global mindset from day one so you can create a product for a global market.”
Despite Cuttable’s growing international presence, Kroonenburg says the thing driving him remains surprisingly simple.
“I just love making things,” he says. “I remember the first time I used Spotify or picked up an iPhone and thought, ‘I can’t believe this exists.’ That feeling never leaves you. For me, that’s what building great products is all about.”
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