Tiffany Haynes: Leading Through Acquisition and Parenting

Tiffany Haynes, former COO of Fingercheck, successfully led the HR platform through a $150 million acquisition in October 2024. Her career began at Jack Henry & Associates in a call center, where she worked for 20 years before becoming a vice president.

As a mother of five and former foster parent to seven, Haynes credits her husband for managing childcare during her extensive travel to New York. Following the acquisition, the couple co-founded a school in Missouri, where her husband serves without a salary. Haynes advocates for daily communication to support each other's domains and prioritizes teaching her children the importance of hard work and emotional intelligence.

Tiffany Haynes began her professional journey at the age of 19, working full-time at night in the call center of Jack Henry & Associates while enrolled in college. She described the role as gritty and hands-on, noting that she did not have a typical college experience because she worked to pay for her car and home. Haynes adopted a proactive approach to her career, stating, "I put my hand up any chance I could."

Despite not considering herself the smartest person, she relied on hard work and a willingness to solve problems. She noted, "I couldn't afford to fail, personally or professionally." This mindset helped her build a reputation for executing tasks with excellence and empathy. By the time she left Jack Henry in 2022, she had risen to the position of vice president after 20 years with the company.

Haynes' reputation led Fingercheck, a New York-based HR platform, to recruit her to scale the company with the goal of acquisition. Despite living in Missouri, she began traveling frequently, spending two weeks at a time in Brooklyn. During this period, her husband managed the household and childcare, loading up the children and taking them to the school where he served as superintendent.

Over three years, Haynes helped scale the company. In October 2024, Fingercheck was acquired for $150 million. She remained with the company until July of the following year to assist with the transition. She described her work in New York as fast-paced, urban, and growth-focused, contrasting it with the rural, quiet, community-focused work her husband does in Missouri.

Following the acquisition, Haynes planned to rest and reorient herself. However, the school her husband led, which was affiliated with a local church, grew too large for the church to manage. The couple faced a choice: let 100 children find a new school or open their own. They chose the latter, launching a new school in a whirlwind four-month effort.

Haynes refers to herself as the "quiet cofounder" and is not involved in day-to-day operations. Her husband does not take a salary for his work at the school, viewing it as their way of giving back. Haynes became the breadwinner when her husband left his paying job 13 years ago to enter education. She supports the school because "he loves the school and I love him."

The couple connects almost every morning over coffee before the children wake up to discuss how they can support each other. Haynes notes that this practice has become easier since she left Fingercheck.

Having grown up poor, Haynes understands her family's current privilege and aims to give back not just money but time. She strives to be the advocate she never had for her own children and the foster children she has raised. She has worked to process trauma from her difficult childhood to provide a foundation of emotional intelligence and health for her kids.

Haynes wants her children to understand the joy that comes from hard work and consistency. She expressed concern that YouTube influencers discussing easy wealth create a short-sighted view of work ethic. She hopes to provide a space where her children can sit with frustrations and build resilience, believing this will serve them well in life.