In a webinar earlier this year, New Charter CEO Peter Melby described AI as exciting and dangerous and said, “It will change a lot in the way we operate.”
To help navigate customers through these changes, New Charter -- No. 11 on the 2026 MSP 501 – has named Jason Rincker director of AI business development. Rincker had been CRO of New Charter-owned Stronghold Data.
“The role is around the growth and strategy of AI,” Rincker said of his new job. “When I say strategy, I mean we're leading a charge to really meet with clients and prospects — not just understand their journey but understand what they're trying to solve. So there's a deep consulting layer to this role, with go-to-market obviously tied in behind it.”
Rincker’s new role can be seen as an expansion of what he has been doing at Stronghold Data, which portfolio MSP New Charter acquired in 2021. Rincker worked with Stronghold’s development team on AI solutions and has been deeply involved in educating clients -- he’ll speak at more than 60 industry events this year. He sees his job as helping customers find ROI on their AI investment rather than treat AI as a shiny new tool.
“I’ll work with all New Charter operating companies and teach them what I've been doing at Stronghold with AI since 2023,” he said. “We’ll use the strategy, the approach, the consulting piece to build up a sales force across the entire [New Charter] platform, with consulting at the forefront and growth right behind it.”
Rincker said the clients and prospects he talks to are “all over the place” when it comes to implementing AI. He said he recently spoke with a large company with a full IT team that has “complete paralysis around AI. They don't even have an AI policy. Their IT director told me flat out he's scared. Meanwhile other people in the room are already using all kinds of different tools on their own. You could see the pain on that IT director's face. That organization just needs somebody to hold their hand — that's why the consulting piece matters so much.”
He also met with a smaller prospect that has built AI applications and has accomplished most of what it needs using Anthropic’s Claude. “They just need help finishing,” Rincker said. “Before they start dumping proprietary information into it, they want to take it the rest of the way, get it containerized, secure, maintained, with the right tweaks. They did a good job. They used the tools well and knew when to call in the experts.”
New Charter’s overall AI strategy includes several pieces – AI enablement, AI solutions and tools, customer AI development and AI security. It acquired Orchestrate AI in 2025 to develop AI models. New Charter’s AI enablement team led by Nick Pope provides clients and prospects with a roadmap for using AI. New Charter’s development team can build customer AI applications for customers, whether they are large enterprises or small shops.
“My job is to go out, teach, and grow the relationships,” Rincker said.
A big part of that job involves making clients comfortable with AI.
“You have to help them overcome their fears — fear of hallucinations, fear of security issues, fear of losing their jobs to AI,” Rincker said. “There's a lot of fear wrapped up in those early conversations that you have to walk them through.”
We’ll watch closely to see how New Charter and other leading MSPs help customers work through these issues.
Rincker will be on the AI Revenue Architects: Meet the New Generation Transforming the Channel panel Sept. 29 at the MSP Summit.