Advancing small-business payments: Dru Armstrong

When people started conducting business in person again after the COVID-19 pandemic, they didn’t go back to their old habits. Instead, their payment activities became more digital than ever. 

It’s been hard for small businesses to keep up. 

“There’s still a fear among a lot of small firms that it’s going to cost them more time and money to change, but as payments have gone digital they’re realizing it’s overall a huge benefit to have people pay in the office at the time of service, instead of mailing an invoice or having customers read their card numbers over the phone later,” Dru Armstrong, CEO of AffiniPay, said in a February interview with American Banker.

Armstrong’s firm is a 20-year-old fintech based in Austin, Texas, that offers online payment acceptance services and software to small legal and accounting firms. These are companies that have long handled business by check — and are starting to get curious about accepting other forms of payment in the office.

To help these companies join the digital age, AffiniPay needed to round out its own offerings. A major milestone in this effort was the 2022 acquisition of MyCase, which enabled AffiniPay to offer expense management and a virtual Visa card, which launched this year.

AffiniPay’s work is far from over. “The great challenge in 2024 is how generative AI will impact the fintech industry to accelerate business operations and simplify professionals’ workflows,” Armstrong said. “We want to take on this pivotal shift in the industry of incorporating these tools and permanently invest to further our position of being one of the most trusted solutions in the fintech industry.”

These efforts will require strong leadership, Armstrong said. AffiniPay will focus on identifying trends and remaining flexible enough to adapt to them rapidly, she said. 

Armstrong joined AffiniPay as CEO three years ago. Previously she was CEO of Grace Hill, a real estate technology firm, and co-founder and CEO of Lily Pod, a consumer technology provider focused on parents and caretakers.