PS27 Blog Post by Jai Raj
At PS27 Ventures, the relationship with a founder starts at the investment-and stays active long after. PS27 is a venture capital firm based in Jacksonville, Florida, investing primarily in B2B software and financial technology companies using AI to solve meaningful business problems. The focus is on founders building businesses that solve real problems, then helping those founders succeed after the investment is made.
That commitment to staying involved is at the core of everything PS27 does.
Our Investment Thesis
Investment Manager Hale Bullen summarizes PS27’s focus as “sticky plumbing software solutions serving the enterprise and financial service technologies.”
Behind that phrase is a straightforward investment philosophy.
“Sticky” software becomes deeply integrated into a customer’s business, making it difficult to replace because it’s essential to daily operations. “Plumbing” refers to the behind-the-scenes infrastructure that powers businesses, including payments, compliance, onboarding, data management, security, and other systems customers rely on every day.
Enterprise software and financial services are especially attractive because many organizations still operate on outdated technology. As AI transforms how businesses work, PS27 looks for founders building products that make these systems more efficient, intelligent, and scalable. If a company is solving a significant problem in a large market and is led by an exceptional founder, it’s a company worth exploring.
Another key part of PS27’s investment thesis is traction. Most portfolio companies already have paying customers before receiving an investment. Revenue demonstrates that the product solves a real problem and that the founder has proven an ability to sell, execute, and learn from customer feedback.
Inside the PS27 Approach
At PS27, being hands on isn’t a talking point- it’s how we operate. When we invest in a company, we show up: weekly calls, strategy sessions, marketing support, and introductions to the right people at the right time. For our founders, that involvement starts at day one and doesn’t let up.
After investing, the team works closely with founders through regular strategy sessions and weekly conversations to help solve challenges as they arise, rather than waiting until the next quarterly update. Whether the discussion is about product strategy, hiring, fundraising, customer acquisition, or scaling operations, the goal is to help founders make better decisions faster.
The support extends well beyond strategy. PS27’s Christine Caven actively helps portfolio companies with marketing and public relations, leveraging relationships that have led founders to appearances on Shark Tank, Good Morning America, and The View, along with media coverage in publications including Forbes, TechCrunch, and Entrepreneur.
The firm’s network, known as the “PS27 Ring of Fire,” is another advantage. Founders gain access to introductions with enterprise customers, financial institutions, strategic partners, experienced operators, potential hires, follow-on investors, and even future acquirers. Those relationships can often accelerate growth just as much as the capital itself.
PS27 believes that honest feedback is one of the most valuable things an investor can provide. Rather than simply agreeing with founders, the team offers direct, constructive advice designed to help companies improve more quickly. As portfolio founder Manuela Zoninsein, CEO of Kadeya, has noted, a fast feedback loop helps founders learn and adapt much faster. That is an important advantage in building an early-stage company.
Built by Operators
One reason PS27 is able to provide this level of support is because its team has spent decades building and leading businesses themselves.
General Partner Jim Stallings previously led IBM’s $25 billion global hardware sales division, managed its $7 billion Linux software business, and oversaw an intellectual property portfolio containing more than 39,000 patents – noted on the 2026 Alchemist Podcast. Before IBM, he graduated from the U.S. Naval Academy and served as a Captain in the Marine Corps. Today, he serves on the boards of FIS and Cannae Holdings.
Across the firm, team members bring backgrounds in technology, finance, operations, and corporate strategy. Because they’ve experienced many of the same challenges founders face, they’re able to provide practical guidance instead of purely financial advice.
The Results
Since its founding, PS27 has invested in more than 25 companies, several of which have been successfully acquired. Collectively, those companies have created more than 1,700 jobs.
Current portfolio companies include Neural Payments, OnRamp AI, Ottometric, QuickCode, and RYZE Superfoods. While they operate in different industries, they all share the same foundation of solving meaningful problems, building technology that customers depend on, and partnering with investors who remain actively involved after the investment is made.
The Bottom Line: THINK BIG, start small
At PS27, success isn’t measured by how many companies receive funding. It’s measured by how many founders build enduring businesses.
The firm invests in AI-powered B2B software and FinTech companies with early traction, but what founders receive is more than capital. They gain experienced operators, strategic advisors, and long-term partners committed to helping them grow.
That’s what makes PS27 different.
Founders who are looking to raise venture capital can submit your pitch deck here.