Technically Legal - A Legal Technology and Innovation Podcast

AffiniPay's Evolution: From Payment Platform to Practice Management Software and Beyond (Dru Armstrong, CEO)

Aug 28, 2024

Dru Armstrong, CEO of AffiniPay, a key player in legal fintech, dives into her journey from aspiring lawyer to leading a groundbreaking practice management software company. She outlines AffiniPay's transition from payment processing to acquiring MyCase, creating an all-in-one solution for law firms. Dru also discusses innovative offerings like Affirm's buy now, pay later service, touches on AI integration plans, and shares insights on the unique challenges and surprises of being a CEO in the evolving legal tech landscape.

43:02

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Episode guests

Dru Armstrong

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Episode notes

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Quick takeaways

Dru Armstrong's journey from aspiring lawyer to CEO of AffiniPay illustrates how diverse experiences can shape effective leadership in tech.

AffiniPay's expansion into practice management software and the introduction of AI tools aim to streamline legal workflows and enhance client services.

Deep dives

Drew Armstrong's Journey to Affinipay

Drew Armstrong transitioned from her initial aspiration of becoming a lawyer to a successful career in the tech business, ultimately joining Affinipay as CEO. After attending law school at the University of Chicago, she recognized that the traditional legal path wasn't the right fit for her, leading her to pursue an MBA and later work with Boston Consulting Group. Her varied experiences, including working in culinary arts and co-founding a baby monitor startup, have equipped her with unique insights into leadership and business operations. Drew's decision to join Affinipay was influenced by her father's struggles as a lawyer in managing the business side of his practice, motivating her to improve systems that help lawyers get paid efficiently.

Intro

2min

Navigating Career Paths: Legal Insights and Personal Growth

17min

From Property Management to Legal Technology Leadership

5min

The Realities of CEO Leadership

3min

Transforming Legal Tech: A Personal Journey

9min

Innovative Financial Solutions in Law

9min

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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Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

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