Oak Street Funding is a specialty lender based in Indianapolis, Indiana. It provides commercial financing to insurance agencies, brokerages, and carriers nationwide. Insurance is one of several verticals it serves. The others are certified public accountant (CPA) firms, registered investment advisors (RIAs), and buy-here-pay-here (BHPH) dealerships.
The company built its name on cash-flow-based loans for insurance professionals, starting in 2003. It later applied that same lending model to those other industries. It is now a subsidiary of First Financial Bank. This profile focuses on its insurance-lending business, covering everything from agency acquisitions to carrier growth capital.
Website: oakstreetfunding.com
Head office address: 8888 Keystone Crossing, Suite 1700, Indianapolis, IN 46240
Founded: 2003
Founder: Rick Dennen
Company type: subsidiary of First Financial Bank, itself a subsidiary of publicly traded First Financial Bancorp (Nasdaq: FFBC)
Business focus: specialty commercial lending for insurance agencies, brokerages, and carriers, one of several lending verticals the company serves
Regions served: nationwide, across the US
Rick Dennen founded the company in 2003 to fill a gap he saw in insurance lending. Agencies needed loans built around commission-based cash flow. Conventional banks rarely offered that at the time.
The pattern across these milestones holds steady. Each step extends the same cash-flow lending model to a related but new client base. That base might be a professional vertical or a newly acquired book of business.
The Westfield integration fits that mold too. It arrived through the parent bank’s acquisition, not a move by Oak Street Funding into a different industry. It deepened the company’s footprint in the same insurance and RIA lending markets it already served.
The lender’s insurance-focused products are built around how agencies actually generate revenue. That revenue is largely commissions and renewals, rather than fixed assets. That reality shapes the loan types it offers:
Each loan type lines up with a stage in an agency’s life cycle. That cycle runs from a first acquisition through an eventual sale or leadership change. Oak Street Funding markets these products separately to agencies, MGAs, and carriers. The underlying approach stays the same across all three: lending against future cash flow instead of hard collateral.
Most insurance agencies turn to niche lenders when traditional banks will not finance a purchase built on commission income. That gap is where the company has operated since 2003, backed by a regulated bank rather than outside capital markets.
That backing sets Oak Street Funding apart from many independent specialty lenders. The parent relationship gives it access to First Financial Bank’s balance sheet. Its narrow focus, meanwhile, keeps underwriting closer to how insurance agencies actually run than a generalist bank’s underwriting would.
The Westfield conversion was completed in March 2026. It extended the same lending model to a wider base of agency and RIA clients. That is a broader footprint, not a new line of business. Its growth so far has come from doing one thing well. It took cash-flow lending for insurance professionals and applied that model to more clients and more verticals over time.
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