Canva shopper-in-chief Cliff Obrecht’s belief that it’s better to buy than build has continued with two more acquisitions, both from the sibling founders of Stayz.
The design platform has now snapped up eight startups and scaleups in two years. This is the 4th and 5th in 2026 – the latest two coming just a fortnight after spending a rumoured $30 million on digital outdoor advertising startup Doohly.
The two Australian tech platforms being bolted on to Starship Canva are Simtheory, an AI collaboration and agent management platform, and Ortto, a customer data and marketing automation company.
As usual, Canva did not disclose the acquisition cost.
But once again VC firm Blackbird, which has Canva as its golden goose, finds itself on both sides of the deal, having backed Sydney-founded Ortto, including a US$12 million (then A$16m) raise in 2017.
Ortto launched 2012 as Autopilot, before rebranding in 2022, and all up raised $46 million from the likes of Rembrandt Venture Partners, Salesforce Ventures, and Southern Cross Venture Partners. The size of the investment suggests Orbrecht put at least eight zeros following the first number after the $ sign to seal the deal. Read more of Startup Daily’s coverage of Ortto, nee Autopilot here.
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Simtheory is a more recent beast, kicking off as a podcast 3 years ago before evolving into a secure workspace for teams to use AI, raising a $5 million Seed round 12 months ago.
Both companies were built by Stayz founders Chris and Mike Sharkey who exited that holiday rentals platform to the former Fairfax Media (now part of Nine). The duo stay on at Canva, taking leadership roles in AI and marketing technology teams.
Complementary AI
Obrecht says that together, they bring complementary strengths across agentic AI, data infrastructure, marketing automation, and customer engagement. Simtheory will have a starring role in next week’s Canva Create on April 16, which the cofounder and chief operations officer as “the biggest transformation” in the privately-owned company’s history.
“This acquisition marks an important step toward evolving Canva from a design tool into the system where work happens end-to-end, whether it’s a quick idea or a full campaign,” Obrecht said.
“Simtheory accelerates our evolution from a design platform with AI tools to an AI platform with design and productivity tools at its core. At the same time, Ortto strengthens our ability to power the entire marketing and content lifecycle through Canva Grow.”
Obrecht’s itchy acquisitive finger kicked off 2026 by snapping up US startup Mango.AI while it was still in stealth mode, as well as the UK’s Cavalry.
Since 2024, Canva’s also gobbled up UK rival Affinity and local generative AI platform Leonardo as well as MagicBrief last year.
Mike Sharkey said: “From day one, we’ve been working to make complex things simple with both Simtheory and Ortto, and we can’t wait to continue doing that on an even larger scale as part of Canva.”
Canva topped $4 billion in annualised revenue last year, and is considering going public with a listing in the US later this year.
The business was valued at $65 billion following a secondaries share sale in mid-2025.
