The CODEW | Build vs Buy Series, Part 3
OpenAI's usage market share slid from roughly 50% in 2023 to 27% by the end of 2025, while Anthropic pulled ahead to a reported 40% share of enterprise large-language-model usage. That gap is the backdrop for what happened next: OpenAI, a company that made a single acquisition in 2023 and two in 2024, closed six acquisitions in the first quarter of 2026 alone — nearly matching its entire 2025 total in ninety days. It now counts 17 confirmed acquisitions since 2023. Few companies illustrate the build-vs-buy tension as starkly, or as publicly, as OpenAI's sprint toward an IPO.
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| Photo by Solen Feyissa/Pexels Close-up shot of a smartphone screen showing the OpenAI website with greenery in the background. |
Buying Its Way Into a Full-Stack Platform
The acquisition list reads less like a coherent roadmap and more like an attempt to plant a flag in every market at once: io (hardware, $6.5B), Statsig (analytics, $1.1B), Astral and Promptfoo (developer tools and AI security), Torch (health records), Hiro (financial planning), TBPN (media), OpenClaw (AI agents), and Weights.GG (voice cloning), among others. Eight of the seventeen deals involve open-source components — a deliberate play for developer-ecosystem goodwill, not just product capability.
Layered on top of the acquisitions is OpenAI Deployment Company, launched in May 2026 with $4 billion in initial capital from 19 outside investment firms and consultancies, majority-owned by OpenAI itself. Its first move was to announce the acquisition of Tomoro, an applied-AI consulting firm, bringing roughly 150 forward-deployed engineers in-house. The logic: models and APIs alone don't close enterprise deals — someone has to sit inside the customer's workflows and actually wire the thing up. Rather than building that consulting muscle from scratch, OpenAI bought it, twice over (Tomoro, plus the earlier Convogo acquisition).
The People Move That Signals the Real Strategy
Alongside the acquisitions, OpenAI brought back Barret Zoph — a former VP of post-training inference who had left to co-found Mira Murati's Thinking Machines Lab — specifically to lead enterprise sales. That's a build-vs-buy decision about talent, not technology: rather than grow enterprise sales leadership organically, OpenAI re-acquired a known executive. It's the clearest sign yet that closing the enterprise gap with Anthropic is now a top-level priority, not a side project. OpenAI also expanded its partnership with ServiceNow, giving ServiceNow's customers direct access to OpenAI models — a distribution shortcut rather than a head-on sales campaign.
The Comparison That Makes the Strategy Legible
Anthropic's approach is the mirror image: just three known acquisitions total (Bun and Humanloop in 2025, Vercept in 2026), while putting its capital into compute — including an April 2026 partnership with Google and Broadcom for 3.5 gigawatts of TPU capacity, alongside run-rate revenue reportedly surpassing $30 billion. Where OpenAI is buying breadth across a dozen categories, Anthropic is buying depth in the infrastructure that lets its existing model scale. Two frontier labs, two completely different answers to the same build-vs-buy question, running at the same time.
Why This Is Also a Warning Sign
OpenAI closed a $122 billion funding round in March 2026 at an $852 billion valuation, giving it more acquisition capital than any startup buyer in history. But it's also projected to burn roughly $17 billion in 2026, and the acquisition spree hasn't been free of scar tissue: the company's planned $3 billion purchase of coding tool Windsurf collapsed in mid-2025 over an intellectual-property dispute with Microsoft, and Windsurf was ultimately acquired by Cognition instead — OpenAI's largest attempted deal at the time, resulting in nothing. A scattered portfolio spanning LaTeX editors, podcasts, and financial planning tools alongside enterprise security and developer tools has also drawn skepticism from analysts about whether there's a coherent strategic center or just a very well-funded shopping spree ahead of an IPO narrative.
The Takeaway
OpenAI's enterprise problem isn't a model-quality problem — it's a distribution and trust problem, the same kind Anthropic has been quietly winning. Buying consulting firms, security tooling, and forward-deployed engineering talent is OpenAI's attempt to close that gap faster than it could ever hire and train its way there. Whether 17 acquisitions in three years add up to a platform or just a pre-IPO growth story is the open question the market will spend 2026 answering.
Previously in the series: Microsoft's Acquisition Strategy Explained. Next: Why Cybersecurity Companies Prefer Acquisitions.
Erwin Castro
Founder & Editor • The CODEW
Erwin Castro is the founder and editor of The CODEW, covering technology mergers and acquisitions, startup exits, artificial intelligence, enterprise software, and Build vs Buy strategy. With more than a decade of journalism experience, he has contributed to Sportskeeda, IBTimes, University Herald, US Blasting News, and Seeking Alpha. His work focuses on explaining the business strategy behind technology deals and their impact on the global technology industry.
Reviewed by Erwin Castro
on
Wednesday, July 08, 2026
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