From the Ground Up
Khary Penebaker
I build companies, lead teams, and fight for what matters.
Regional General Manager at Great Day Improvements, leading operations across six Midwest markets. Nearly 30 years of building companies, teams, and movements — from a $1.5M startup to a $35M multi-state operation. Survivor. Advocate. Father.
As Featured In
What I Do
Construction Industry Leadership
Nearly three decades of experience in commercial roofing, building envelope solutions, and multi-state operations management. Expertise in EPDM, TPO, GAF systems, sheet metal fabrication, and large-scale project delivery.
Advocacy and Public Speaking
Keynote speaker on gun violence prevention, survivor advocacy, resilience, and leadership. Available for conferences, panels, corporate events, and community organizations.
Team Building and Turnarounds
Proven track record of taking underperforming operations and building them into high-performing teams. From hiring and training to systems and culture, I build organizations that deliver.
Recent Posts
- The State of Home Improvement in 2026: Trends to Watch
Nearly 30 years in the industry, from commercial roofing to running four markets for Great Day Improvements. Here is what is actually happening in home improvement in 2026 and why a lot of it is being misread. - Why Every Professional Needs a Personal Website in 2026In 2026, every professional needs a personal website. Learn why your site is your most valuable career asset and how to build one that works for you.
- Why I Still Fight: My Story of Gun Violence PreventionGun violence prevention advocate Khary Penebaker shares his personal story of losing his mother to gun violence and why he continues to fight for change.
about me
From the Job Site to the National Stage
executive
Leading home improvement operations across six Midwest markets with nearly 30 years of industry expertise.
advocate
Gun violence prevention advocate and survivor. Fighting for safer communities.
entrepreneur
Founded Penebaker Enterprises, grew it from $1.5M to $12M in commercial roofing.
I started Penebaker Enterprises in 2002 with a truck, a phone, and a willingness to outwork everyone in the room. Built it from $1.5 million to $12 million doing commercial roofing and sheet metal fabrication, the kind of work where cutting corners isn’t a strategy, it’s a liability. EPDM, TPO, GAF systems, building envelope work that had to be right the first time.
Then I joined Roofed Right America and did it again at a different scale. Took the company from $6 million to over $35 million in annual revenue, 180 employees, five states. I didn’t inherit that. We built it from nothing, and that means building the people, the culture, and the systems before you ever worry about the numbers.
Today I run the Upper Midwest region for Great Day Improvements, covering Chicago, Madison, Milwaukee, and Minneapolis. Nearly 30 years in this industry and I still believe the fundamentals are the fundamentals. Hire right, train hard, show up.
But the business has never been the whole story.
My mother Joyce died by suicide with a gun when I was 20 months old. I never knew her. That loss has shaped everything I’ve done outside of work, and a lot of what I’ve done inside it. It’s why I ran for Congress in Wisconsin’s 5th district in 2016. It’s why I spoke at the Democratic National Convention. It’s why I served as a DNC representative for Wisconsin and why I’ve spent years as an Everytown for Gun Safety fellow. You don’t get over something like that. You just decide what to do with it.
I live in Waukesha with my fiance Anne. I have three kids, Josie, Kyan, and Sydney. I collect sneakers, I’m on TikTok more than I probably should be, and I still believe showing up is 90% of the job.
What People Say
Khary is the kind of leader who makes everyone around him better. He built our team culture from scratch, and the results speak for themselves.
His advocacy work is deeply personal and that authenticity is what makes it so powerful. Khary doesn’t just talk about change, he shows up and does the work.
One of the most compelling speakers I’ve seen. Khary connects with any audience because he leads with honesty and doesn’t hide behind a script.
My Socials
Follow my professional journey in construction leadership, regional management, and business strategy.
Professional updates, career insights, and leadership in construction and advocacy.
Advocacy, political commentary, and real-time conversation on the issues that matter.
Community updates, personal stories, event highlights, and behind-the-scenes moments.
In The Media
Khary has been featured in national and local media for his advocacy work, business leadership, and personal story.
2020 DNC Convention speaker and Everytown fellow
Shared his story of loss on the national stage to fight for gun violence prevention.
Featured in national and local media across Wisconsin
Milwaukee Journal Sentinel, Everytown for Gun Safety, Moms Demand Action, and more.
Featured In
2020 Democratic National Convention — spoke about gun violence prevention and his mother Joyce. Milwaukee Journal Sentinel — coverage of Congressional campaign and advocacy work. Everytown for Gun Safety — featured fellow and spokesperson. Moms Demand Action — speaker and organizer at events across Wisconsin. For media inquiries, contact info@kharypenebaker.com
Leaders Who Make a Difference
Featured at the 2020 Democratic National Convention, sharing his personal story of losing his mother Joyce to gun violence when he was just 20 months old.
Giving back has always been
extremely important to Khary.
Khary has been featured across national media for his advocacy work, political campaigns, and community leadership.
Congressional Candidate
Everytown Fellow
DNC Delegate
advocacy & leadership
A dedicated advocate for common-sense gun legislation and community safety, working with elected officials and grassroots organizations.
From Construction Sites to Capitol Hill.
Passionate about mentoring the next generation of leaders in both business and civic engagement.
Why Gun Violence Prevention Is Personal.
Building stronger communities through action, not just words. Every project, every campaign, every conversation matters.
