When AI powerhouse OpenAI took an equity stake in venture capital company Thrive Holdings earlier in December,
Jessica C. Davis, principal analyst for managed services with Omdia, immediately saw it as a harbinger of things to come in the world of enterprise AI services.
“The investment puts the spotlight on how AI is poised to change the MSP business,”
Davis wrote in a LinkedIn post. “It won’t be an overnight change. But investors and AI companies smell opportunity in managed services.”
The terms of the equity stake that OpenAI took in Thrive Holdings were not disclosed, but the move shows OpenAI’s interest in building enterprise and market demand for AI services by investing in MSPs and other service providers that can advance this mission. Under the deal, OpenAI will also focus on building relationships with accounting service providers, which, like IT services providers, run high-volume, rules-driven, workflow-heavy processes where OpenAI’s platform can drive immediate benefits, according to OpenAI.
Making OpenAI’s investment even more intriguing is the fact that Thrive Holdings, in June, joined private equity firm ZBS Partners to help launch a new AI-enabled managed IT services platform,
Shield Technology Partners, by providing initial funding of more than $100 million. Shield was made up of four IT services firms at its June launch and has since added four more, bringing the total to eight partners, with more expected in 2026 and beyond.
This is all notable, wrote Davis, because under the equity deal OpenAI will be compensated for its stake through future financial returns from Thrive Holdings, and the partnership grants OpenAI access to the companies’ data to train its AI models. OpenAI also plans to embed its own research, product, and engineering teams inside the service providers involved with Thrive Holdings to boost speed, accuracy, performance quality, and cost efficiency, according to the partners.
OpenAI Can Leverage MSP Investments to Drive Its LLM Business: Analysts
Several other IT analysts said OpenAI’s equity investment in Thrive Holdings clearly shows the company’s deep interest in driving and growing enterprise AI adoption of its large language models directly through trusted service providers.
“AI deployment requires a fair amount of expertise that many companies, especially SMBs, do not have,”
Jack E. Gold, president and principal analyst with J. Gold Associates, LLC, told ChannelE2E. “So they go to MSPs to get the tools and apps they need. OpenAI sees this investment opportunity as a way to advantage its own products over other AI providers as it courts MSPs.”
Gold called the move “a revenue-enhancing and market-protection play” that he expects to see from other LLM vendors in the future as well. “It is fairly common for deep-pocketed companies that want to solidify market-share dominance to make these kinds of investments,” said Gold.
R. Ray Wang, founder and principal analyst with Constellation Research, called MSPs a key distribution channel for LLMs, which makes them important for companies like OpenAI.
“As OpenAI moves from product-led growth to sales-led growth, you will see more enterprise motions,” said Wang. “What did surprise me was the timing and focus. We are seeing both OpenAI and Anthropic enter the market for enterprise customers.”
Asked if the move is OpenAI’s reaction to slowing AI market growth, Wang said he does not see it that way. “I do not see this as a reaction to a stalling AI market, but more as an enabler for the future.”
OpenAI Taking an MSP Ownership Stake Is a ‘Bold Move’
Another analyst,
Zeus Kerravala, founder and principal analyst with ZK Research, said OpenAI definitely needed “a bridge to the enterprise,” but that “taking an ownership stake is a bold, inside-out strategy. Usually, tech companies build a partner program and wait for MSPs to sign up. By investing directly in Thrive Holdings, which acquires and builds companies, OpenAI is essentially building its own living lab.”
But Thrive Holdings’ MSP strategy goes even further, said Kerravala. “They are not just selling software to MSPs — they are embedding their own engineers into the MSP workflow to figure out exactly where the friction is.”
Part of the market problem for OpenAI today is that “it has hit a complexity wall,” he said. “Enterprises have moved past the ‘playing with ChatGPT’ phase. They are now facing the reality that deploying AI in a rules-driven environment like accounting or IT services requires deep integration with legacy systems, data privacy and sovereignty, and workflow re-engineering.”
For OpenAI, the company “likely realized that frontier models alone will not close the deal going forward,” said Kerravala. “You need the domain expertise that MSPs possess. If adoption feels slow, it is because the transition from generative AI — writing emails — to agentic AI — closing books or resolving IT tickets — is a massive engineering hurdle.”
In its original announcement about its Thrive Holdings equity investment, OpenAI said it sees the move as a repeatable model with other MSPs, noted Kerravala. “This suggests that OpenAI views the channel — specifically MSPs — as the primary distribution engine for the next phase of AI. For the channel, this validates the MSP’s role not just as a service provider, but as an AI implementation partner.”
In addition, the equity deal’s initial focus on providing accounting and IT services is telling, said Kerravala. “These are the bread and butter of the MSP world. These are the perfect training grounds for test-time compute — the long-thinking models like OpenAI o1, where the AI needs to follow a sequence of complex steps rather than just predicting the next word.”
At the same time, competitive pressures continue to grow for independent MSPs, said Kerravala. “If OpenAI is embedding its own engineers into Thrive-owned companies, those specific firms will likely gain a massive competitive advantage in speed and cost efficiency,” he said. “This may force independent MSPs to accelerate their own AI-forward strategies to avoid being commoditized by AI-native competitors backed by
Frontier Labs.”
To Kerravala, OpenAI’s investment in Thrive Holdings "is a sign of maturity.” He said, “OpenAI is moving from Silicon Valley hype to Main Street deployment. For the channel, the message is clear: The next billion dollars in AI value will not be made by the people building the models, but by the people embedding them into the mundane, complex workflows of everyday business.”
OpenAI Is ‘Scrambling,’ Says Analyst
Another analyst,
Shelly Kramer, founder and principal analyst with Kramer & Co., told ChannelE2E that she sees OpenAI’s equity investment in Thrive Holdings as a sign the company is looking for bold new ways to bring in more revenue to cover its costly operations.
“OpenAI is scrambling, and this move is designed to help spur adoption and drive revenue, both of which are sorely needed,” said Kramer. “When you explore the number of ChatGPT users versus paid subscribers, the data tells the story.”
There are about 900 million weekly active users of OpenAI’s ChatGPT, but only about 20 million are paid subscribers across the company’s ChatGPT Plus, Pro, and enterprise offerings, according to Kramer.
“ChatGPT Plus costs $20 a month and has fairly strong retention, with about 89% of users continuing quarter over quarter,” she said. “ChatGPT Pro launched at $200 a month a year ago and has been widely viewed as disappointing in terms of cost-to-value among the developer community, which is the largest user base,” she added. “The percentage of paying users has decreased from 5% to 4% in recent months, despite subscriber numbers growing. Do you think this is an investor concern? You bet.”
For OpenAI, the biggest challenge is convincing users that the service is worth paying for when competitors such as Claude and Gemini continue to grow their user bases, she said.
“All of the above indicates that OpenAI has to do something to drive adoption — and paid adoption at that,” said Kramer. “The competition in the AI wars is fierce, and OpenAI’s ChatGPT is absolutely not the only game in town.”
