Direct Mail to AI-Driven Lending: 25 years funding small businesses

How small business lending is getting faster, smarter, and more human with AI.

The FairSquare family of brands have been in business for over 25 years and offer a wide range of financing solutions to meet the needs of any business owner through their brands National Funding, Finova Capital, QuickBridge and smallbusinessloans.com

AI is changing the speed and scope of financial services, but not at the expense of relationships. Tyler Maran, CEO and Co-founder of OmniAI sat down with Chris Panebianco, Chief Customer Officer at FairSquare, to talk about the rise of financial-services AI adoption, and why even the most advanced tech must put customers first.

Rewiring Small Business Lending with AI

FairSquare have been in the SMB lending business for more than two decades and Chris has seen first-hand a big increase in the use of automation in that time, starting with marketing optimization and evolving into underwriting, funding, and servicing.

“We’re connecting systems, automating applications, document uploads, and even how borrowers link their bank accounts” Chris

Beyond this, AI capability has jumped forward in the last 12 months in areas such as document interpretation, data structuring and analysis - all of which can make small business lending easier and faster for both the lender and the borrower.

“We’ve gone from 'can this work?' to 'this is working better than humans at scale.' Our accuracy has jumped from 80% to 95%. That’s a game-changer.” Tyler

Building an AI Mindset

Security, compliance, and adoption hurdles haven’t disappeared, but they're rapidly falling away as AI can help out with more of the workflow with reliable and high quality output:

“Our legal and compliance teams are catching up fast. That’s what’s unlocked this supercharge across the org.” Chris

Chris now has a team member solely dedicated to AI certifications and tool integrations to ensure FairSquare are utilizing the right tools and implementing them when they're ready. While the initial focus has been on unlocking internal gains to reduce the risks of trying our new technology, he’s now turning his attention to the customer experience.

“The customer is always in the room, literally. We have a picture of one on a chair during meetings to remind us who we’re solving for.” Chris

Tech is also unlocking new products, such as their new NF Express platform which offers fully digital, instant loans up to $50K with no human interaction, and smallbusinessloans.com which plans to add new capabilities and become a full-stack platform for business formation, lending, and insurance.

AI is accelerating the customer experience (and competitors)

Part of Chris's role is to ensure FairSquare are deeply connected to their customers across all of their different brands and products, and AI is making 10x productivity gains possible with the right tools and approach.

Applying new technologies in the right areas is key to unlocking efficiency gains, but it also means smaller, AI-native companies can compete with the established incumbents if they're too slow to adapt.

In this respect, AI is creating a double edged sword where Chris and his team aim to be first among their peers to use AI to unlock the best possible customer experience, while it opens the door to new, AI native competitors.

These AI-native competitors are extremely fast and agile and ultimately the customer benefits from the increased competition:

“You no longer need $50 million and a 100-person team to build something great. We’re seeing 10-person crews do 10x more.” Tyler

Marketing Strategy: Old School Meets AI

Despite being a fintech veteran, Chris surprised Tyler with a proven favorite: direct mail.

“Direct mail is still the GOAT. We’re testing 5–10 creatives at once with dynamic content and personalized offers. And it’s fully integrated with digital and email.” Chris

He’s also investing in branded content, podcasts, CTV, and boots-on-the-ground trade shows. But the foundation is data:

“Without the right data, you’re flying blind. It drives our targeting, messaging, product launches, even how we design customer journeys.” Chris

Chris's marketing mantra is to test everything, fail fast and share the learnings across the org so the company improves at the fastest rate possible.

“Some of our best results came from failed tests. It’s how you adapt that counts.” Chris

Retention Over Acquisition

While it's tempting for companies to relentlessly chase new logos, Chris prioritizes lifetime value.

In world of small business lending, where word of mouth and referrals are a great source of growth, keeping existing customers happy is top of mind:

“The cheapest customer to acquire is the one you already have. We treat funded borrowers like gold.” Chris

FairSquare now dedicates an entire team to post-funding engagement, upsells, and brand loyalty.

“If you’re a startup, treat every customer like your first. That’s where scale comes from.” Chris

Key Takeaways

• AI is reshaping every touchpoint from loan intake to servicing.

• Security and compliance are no longer blockers; they’re catching up through AI.

• Direct mail still works especially when paired with data-driven digital.

• A “customer-first” mindset must be authentic and company-wide.

• Retention should be as celebrated as acquisition.

• Testing and iteration matter more than perfection.