Drew Hiss

Drew Hiss launched his outsourced payroll and HR technology solutions company, Checkdate Solutions, in 1994. The entrepreneurial venture was a classic bootstrap start-up whose launch plan underestimated capital needs and ramp up time by significant multiples. The adventure predictably included scrapping for cash, overhauling the business model, rebranding, refocusing, redirecting resources, shifting tech platforms, praying, seeking counsel and wisdom, etc.. Not surprisingly, deep entrepreneurial scar tissue was forged. Ultimately Checkdate Solutions became one of Kansas City’s fastest growing companies and was named one of the Greater KC areas Top Small Businesses not once, but twice. Additionally, Checkdate Solutions ranked as one of KC’s top 100 fastest growing companies for nine consecutive years and was in the top 25 nationally in its industry.

Today’s workplace culture tends to compartmentalize personal virtues from commerce, creating silos and compartmentalization between business, family, community, values and faith. But as a CEO, Drew and his company grew when he “decompartmentalized:” on his journey, he learned to integrate his life of commerce and his life of family, faith and values.

Drew merged Checkdate Solutions with payroll industry leader Paycor, stepping away from the company in 2008 and serving on its board for eight years. Drew remains an owner in the firm. The two firms have become one of top HCM firms in the US. Paycor completed its IPO in July of 2021 (PYCR).

Drew and his wife, Sarah have been married for 32 years and have four children (plus two beautiful daughters in law) ranging in age from 28 to 22. In early 2020, Drew and Sarah relocated to Evergreen, CO, He is a raving-fan congregant of Flatirons Community Church in Lafayette, CO, and enjoys snowboarding, hunting, cycling, hiking, and a variety of outdoor activities and adventures including running with his two dogs.