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Meet Dru Armstrong, leading the charge as one of Fintech’s Most Influential Women!

by Krishnendu P
by Krishnendu P

With experience and learnings from different backgrounds like culinary skills and law and then to be at the forefront of fintech, this lady ensures that she not only impresses everyone that crosses her but also be a flagbearer of success and perseverance. Introducing Dru Armstrong, named one of the most influential women in fintech by Americal Bankers 2024. 

A Tapestry of Experiences

Dru Armstrong had diverse career paths, thanks to her family legacy – Culinary and Law. As Dru dabbled in both areas, she found them lacking the spark to ignite her passion. It was then that she transitioned her career into business. She embarked on this journey of discovery and learning, ultimately taking her to the helm of AffiniPay. 

A Journey to Success

Tragedies and life’s curveballs that one faces often shape our careers and destinies. For Dru, her life took a turn for happiness with her pregnancy but then it all came down crumbling when her husband came face-to-face with a health scare. This saw a shift in her priorities and Dru began looking for a job with a solid paycheck. This search ended right at Grace Hill’s doors, a real estate technology firm that services property management companies. With her strong problem-solving skills and sharp business acumen, she soon became the CEO of Grace Hill. 

Fintech Revolution

Being at the helm of AffiniPay, Dru has not only authored a saga in fintech but has also infiltrated a male-dominant realm and planted her flag there. Her visionary leadership has propelled AffiniPay to the forefront of online payments and software solutions, with a focus on serving the needs of private practice attorneys, associations, and nonprofit organizations. Dru has spearheaded a diverse and inclusive work environment at AffiniPay with 43% of their workforce comprising women. In the accompaniment of bold leaders like Erin Brooks and Catherine Dawson, AffiniPay stands as a beacon of gender equality in the fintech industry.

A Personal Mission:

Dru’s draw towards fintech stems from a great personal loss. Her father, a role model for little Dru, went bankrupt in his last years of life. A successful lawyer, Dru’s father’s downfall started when he ventured into his own business, a law firm. Witnessing this struggle, she found AffiniPay with a core focus on providing payroll and software solutions to professionals like her father, ensuring that they can thrive in their respective fields without succumbing to the pitfalls of financial mismanagement.

Recognition and Impact:

A prominent figure in fintech, Dru Armstrong’s struggles never went unnoticed. The proof of this is her inclusion in American Banker’s 2024 list of Most Influential Women in Fintech. In a sector that records a minor 18% of women in C-Suite positions, Dru’s ascent serves as a testament to the power of resilience, vision, and determination.

Looking Ahead:

With initiatives like the acquisition of MyCase Legal Practice Management Software and the launch of AffiniPayIQ, she remains at the forefront of innovation, shaping the future of fintech one bold step at a time.

In a field where women seldom venture, Dru stands strong with her leadership skills, resilience to friction, and sense of empowerment. Under her able leadership, AffiniPay thrives as a workplace that champions diversity, gender equality, inclusion, and innovation. As she continues to leave her mark on the world of finance and technology, Dru Armstrong’s legacy is one of inspiration and impact.

Dru Armstrong’s Journey to Legacy: A Timeline

  • Explored culinary arts and law, but found them lacking as potential career paths
  • Started career at Boston Consulting Group, gaining valuable business experience
  • Transitioned to a private equity firm and later joined a startup
  • Faced personal challenges including pregnancy and a health scare with her husband
  • Joined Grace Hill, a real estate technology firm, and swiftly rose to CEO within 6 months
  • Oversaw the acquisition of a company run by Kendall Pretzer, known for its female-friendly culture
  • Founded AffiniPay, inspired by her father’s financial struggles, with a focus on providing payroll and software solutions
  • Recognized as one of the most influential women in fintech by American Banker in 2024
  • Acquired MyCase Legal Practice Management Software and launched AffiniPayIQ
  • Appointed to the Ascension Seton Texas Foundation Board of Trustees
  • Championed diversity with a 43% female workforce and prominent female leaders like Erin Brooks and Catherine Dawson at AffiniPa

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