Khary Penebaker
The Short Version
I have been doing it for over 20 years and I am not slowing down.
Right now I am the Regional General Manager for the Upper Midwest at Great Day Improvements, overseeing operations in Chicago, Madison, Milwaukee, and Minneapolis. Before that I founded Penebaker Enterprises and grew it from a $1.5 million startup to a $12 million commercial roofing operation. Then I scaled Roofed Right America to over $35 million with 180 employees across five states.
A Life of Building Through Adversity
Loss That Shaped Everything
My mother Joyce died by suicide with a gun when I was 20 months old. I grew up knowing that absence every single day. It is not something you get over. It is something you carry.
Founded Penebaker Enterprises
Built a commercial roofing and sheet metal fabrication company from scratch. A truck and a phone. Grew it to $12 million before moving on to bigger challenges.
Ran for Congress
Ran for Congress in Wisconsin's 5th District on a platform of gun violence prevention, economic opportunity, and healthcare access. I did not win, but I was not done.
DNC Convention Speaker
Spoke at the Democratic National Convention about my mother, about the cost of gun violence, and about what happens when we do nothing. That same year I became an Everytown for Gun Safety fellow.
Chose Family First
Stepped back from board service to focus on my mental health and my family. That was the hardest and best decision I have made in a long time.
Leading the Upper Midwest
Took on the Regional General Manager role at Great Day Improvements. Building systems, teams, and results across four markets.
Where I Am Now
I am engaged to Anne. Our wedding is November 21, 2026 at The Gage in West Allis. I have three kids -- Josie, Kyan, and Sydney -- and I co-parent well with their mother Amanda.
I collect sneakers (Nike AF1s, Jordans, Yeezys -- size 10.5). I sell on eBay, Poshmark, and StockX. I make TikToks. I am a Mac Miller fan. I believe in showing up, doing the work, and being honest about the hard stuff.
What I Bring to the Table
Construction Expertise
EPDM, TPO, GAF products, building envelope solutions, commercial roofing, sheet metal fabrication
Scaling Organizations
Proven ability to build and scale from startup to multi-state operations with $35M+ revenue
Team Turnarounds
Track record of turning around underperforming teams and markets across multiple states
National Advocacy
National-level advocacy experience, public speaking, and survivor storytelling
Leading Through Adversity
Real understanding of what it means to lead when things are hard, not just when they are easy
Revenue Growth
Driving revenue growth from startup to $35M+, with full P&L ownership and forecasting
Want to Connect?
Whether it is business, advocacy, or just a conversation -- I am always open.
Get In Touch