Rampersand Investment Notes: Cuttable’s $20m Series A

Rampersand VCOct 27, 2026

Rampersand Investment Notes: Cuttable’s $20m Series A

FAST-FORWARD: From making ads to ads that learn

Oct 27

Two years ago, Rampersand backed Sam Kroonenburg (co-founder of A Cloud Guru, which sold for $2bn) and Ed Ring (serial founder, marketer and operator) on a big vision: to build a fully automated AI advertising agency.

We’ve been on the journey since day one, and the team hasn’t just delivered on that vision. It has surpassed it. Along the way, Cuttable launched in the US and grew revenue and the team at warp speed. I still remember walking down a graffiti-covered laneway to find their first office in suburban Melbourne. Lining up a trip to visit the new HQ on Park Avenue in New York.

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Now Cuttable has raised more capital to keep expanding and released the most exciting product yet - ads that learn.

Cuttable announced its $20m Series A, led by our friends at Airtree, with Square Peg and Glitch Capital following on. We’re thrilled to be backing the team again.

Read more about the round in SmartCompany.

❓ Why Rampersand is doubling down

Built on the brand, not on AI slop. Cuttable makes ads from what a brand already owns and has already approved: its photo and video shoots, product catalogue, typography and tone of voice. Every ad is layered and editable, so getting from “nearly there” to “approved” is a quick tweak rather than starting again.
The loop is the moat. Cuttable publishes directly into customers’ ad accounts and reads performance back across everything a brand runs, not just the ads it made. This has evolved to launching “ads that learn”, combining ad results with Shopify and CRM data to tell brands what to publish next. Every round of ads makes the next round smarter, and the dataset compounds with every brand that joins.

“Everyone has taught AI to make ads. Almost nobody has taught the ads to learn.” - Sam Kroonenburg, CEO, Cuttable

Shooting Star Momentum. Cuttable has grown many times over since our initial investment. Revenue has compounded every month this year, hundreds of brands now make ads on the platform, and those ads have driven millions of dollars in spend. As Airtree put it; “growth has been much faster than our (already very high) expectations.”
Exceptional team and velocity. This team’s rare clarity of vision and ability to ship new product every week. In a category moving this fast, speed of execution is a huge advantage.

Product launch video: Ads that learn

💡 The big vision, revisited

In our seed notes, we wondered whether AI could one day create the next “Happy Little Vegemites” or “Not Happy Jan!” on its own.

Our view has evolved. In performance advertising, the prize isn’t one iconic ad. It’s a system that keeps finding the next winner, week after week.

Cuttable is executing on the roadmap to deliver this. First, Cuttable delivered on-brand ads at scale. Now they have delivered ads that learn. From the data across more than $370m in ad spend, Cuttable works out which ads a brand needs next, recommends them, then makes them from the brand’s own footage, so every round starts from what already works.

From here, Cuttable is racing to close the full creative loop, from idea to execution, so ad creative stops being a guessing game. It’s all about learning what works and creating ads which perform.

👨‍🍳 About the team

SamKroonenburg built A Cloud Guru to a global revenue of $100m and a $2bn exit within six years. That demonstrates an incredible ability to execute. However, underpinning this was a clear vision of where the market was moving and a focus on building a solution to deliver it. Sam is a proven unicorn founder.
Ed Ring has grown the business from the ground up—starting in the early days in the marketing team and being the customer, moving to wear all the hats, co-founding Hector’s Deli, and becoming employee #1 at Conscious Investment Management, where he designed, structured, and managed investments in the climate, health and education, and social infrastructure space.

We’re proud to back Sam, Ed and the Cuttable team again as they build the system marketers reach for first. 🚀

If you’re a founder building AI that does the work, not just assists with it, I’d love to chat. Reach out to me.

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