AffiniPay is historically a fintech company with a big presence in legal. Their flagship product is LawPay used by law firms to bill clients and accept payments. Dru joined the company in 2021 and right around that time, the company ventured beyond the world of payment software and acquired MyCase, which is law practice management software used by law firms to keep all case details and documents in a single location, keep track of tasks and streamline client communications.

Growing up, Dru wanted to be a lawyer because she comes from family of lawyers, including her father. She studied law at the University of Chicago, but after a couple of gigs with law firms, she figured out that maybe the law wasn’t for her.

So, she finished her MBA and went to work for Boston Consulting. After a few years as a consultant, she needed a break, and, being somewhat of a foodie, she went to work in the kitchens of some of New York's finest dining establishments.

She took lessons learned from the kitchen into her later work as a co-founder of a baby monitor start-up and ultimately roles as CEO of the property management company Grace Hill and now AffiniPay.

In this episode, Dru talks about:

• Joining AffiniPay and its mission

• The company’s acquisition of MyCase and expansion into practice management software

• Affirm, AffiniPay’s Buy now, pay later product and its impact

• The company’s AI plans and integration within the platform

• Core responsibilities of a CEO and what has surprised her in her role as a CEO

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Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI