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Dru Armstrong
Dru Armstrong is the Chief Executive Officer (CEO) of AffiniPay, a financial technology company that provides practice management software, integrated payments, and embedded fintech solutions to professionals.12389 She assumed the role of CEO in July 2021.34 In October 2024, she was elected to Paycor's Board of Directors.8
Background and Career:
- Armstrong has over 20 years of experience in the technology sector.1
- Before joining AffiniPay, she was the CEO of Grace Hill, LLC, a real estate technology and software provider, from June 2016 to July 2021, and served as their Chief Product Officer from September 2015 to May 2016.3
- Armstrong has experience scaling technology companies with private equity firms, holding leadership, operations, and consulting roles.57
Achievements and Recognition:
- Armstrong was recognized in American Banker’s 2024 list of Most Influential Women in Fintech.4
- Key Executives Publication recognized Armstrong as one of Austin's Top 25 CEOs.6
- Armstrong spearheaded the acquisition of MyCase Legal Practice Management Software and supported the launch of AffiniPay IQ, which integrates generative AI into AffiniPay's products.4
- She was named as a Top 25 Women Leader in PE-Backed Software companies for 2024.7
AffiniPay and its Services:
- AffiniPay has been recognized as one of Inc. 5000’s fastest-growing companies for 12 years in a row.4
- AffiniPay is a market leader in practice management software and online payments for professionals in legal, accounting, architecture, engineering, and construction firms.4
- AffiniPay's brands include LawPay, MyCase, CASEpeer, Docketwise, CPACharge, and AffiniPay for Associations.4
- AffiniPay serves over 150,000 legal, accounting, construction, design, and association professionals.9
Education:
- Armstrong holds a Master of Business Administration from the University of Chicago Booth School of Business, a Juris Doctorate from the University of Chicago Law School, and a Bachelor of Arts in Economics from Columbia University.3
Highlights
Feb 6 · builtin.com
AffiniPay Careers, Perks + Culture | Built In
Jan 14 · affinipay.com
AffiniPay | Practice Management & Fintech for Professionals
Oct 24 · globenewswire.com
Paycor Welcomes Industry Leader Dru Armstrong, CEO of
Oct 24 · investors.paycor.com
Paycor Welcomes Industry Leader Dru Armstrong, CEO of AffiniPay ...
Aug 30 · atxwoman.com
Woman to Watch: Dru Armstrong - Austin Woman Magazine
May 29 · affinipay.com
AffiniPay's Dru Armstrong Earns Spot On Key Executive's Top 25 ...
Jan 1 · investors.paycor.com
Dru Armstrong | Board Member | PAYCOR HCM, INC.
Feb 25 · greathillpartners.com
AffiniPay | Companies - Great Hill Partners
Aug 23 · affinipay.com
About AffiniPay: Our Mission, Core Values, and Leadership



