Meet Grant Woolwine—strategic thinker, sports enthusiast, and the steady hand guiding KEYSYS’ operations forward.
A Journey of Growth
Joined: 2013
Role: Chief Operations Officer
Focus: From translating complex mortgage processes to managing finance, compliance, and operations, Grant ensures KEYSYS runs smoothly while creating opportunities for others to succeed.
Highlights so far
Mortgage Tech Translater → Company Leader: Entered KEYSYS with deep mortgage sales experience, bridging the gap between industry jargon and tech execution.
Versatile Operator: Progressed from sales and account management into administration, finance, compliance, and ultimately, COO—building a broad perspective across the company.
Team Builder: Known for fostering collaboration and creating environments where coworkers achieve both personal and company wins.
Advice to Aspiring Leaders
1. Be a Good Teammate:
Collaboration fuels company growth and personal development.
2. Leverage Your Experience:
Apply what you know in new ways to open doors for yourself and others.
3. Stay Curious:
Each role is an opportunity to learn something that will serve you later.
Why Grant Loves KEYSYS
“The people are incredible at KEYSYS and each day is different.”
People First: Thrives on working alongside talented, driven individuals.
Every Day is Unique: Enjoys the variety and challenges that come with leading operations.
Shared Successs: Finds purpose in helping others grow within their roles.
Outside the Office
Bluegrass Roots: Originally from Kentucky and a devoted fan of all things related to the Bluegrass State.
Derby Whisperer: Picked two of the top five biggest longshots in Kentucky Derby history—Country House (2019) and Giacomo (2005).
Master of Smoke: Creates the sought-after “Woolwine Smoked Salt” and experiments with grilling and smoking new recipes.
Family & Fun:Loves family movie nights, outdoor adventures, coaching soccer, and watching both college and pro sports.
Since joining KEYSYS, Grant has contributed to every single major functional area for us, from sales to accounting, to presently leading our operations. He brings stability and dependability to whatever he does. Maybe most importantly, Grant is at the center of the culture at KEYSYS – helpful, dependable, high work ethic, and proactive. He sets a great example for everyone at KEYSYS.
Grant’s dedication to fostering teamwork, his operational expertise, and his ability to connect people and processes make him an essential part of KEYSYS.
