Drew Hiss

Founder & Growth Catalyst, Kansas City

Drew Hiss 2



"I enjoy business and the stories that lie beneath each entrepreneurial journey, success and challenge...and I love helping others amp-up that journey whether growing the top line, optimizing the bottom line or enriching the storyline (code for having a positive impact on people’s lives today, tomorrow and for the greater-beyond).

My heart is to help business owners win big in the marketplace AND leverage the influence of their business platform for eternal impact on those they lead. This is the heartbeat of Acumen which I founded late in 2015. Acumen is a catalytic iron-sharpening-iron environment forged from the fiery furnace of entrepreneurial battle, marketplace survival and integration of the timeless wisdom of the ages."


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.

More About Drew

Challenges Drew is seeing CEOs facing today.
  • Not knowing
  • Knowing, but not doing (hope is not a strategy)
  • Isolation
  • Busy-ness (constantly in Quadrant 1 - the tyranny of urgent)
  • Way too much time in the business vs. on
  • Lack of true trusted counsel and real-life biz relationships
  • A litany of negative woke cultural forces adversely impacting their cultures

On a personal note...

How I recharge for the day.

Exercise (cycle, run, walk dogs, hike). Solitude. Power 15-minute cat-nap :-D

Words that describe me best.


Favorite activity after work.

Snowboarding, fly fishing, hunting or mountain biking.

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Acumen is an exclusive community of CEOs & Owners focused on helping you grow your top line, optimize your bottom line and enrich your storyline.
Our affinity-centric approach creates a community that’s both an advisory board and a peer mastermind. In combining the best of both, Acumen unifies professionals whose businesses are in similar seasons and have similar characteristics, like revenue, employees, locations, competency, and demographic similarities.


Our commitment...

We develop healthy, growing businesses.
NOT a hospice or lifeline for a sinking ship.
We work on CEO/Business Owner issues.
NOT networking or small group study.
We are humble and teachable.
NOT for the “know it all” or
the person who has “all the answers.”
We share values, virtues & beliefs.
NOT for people whose walk
and talk lack significant alignment.