About Khary Penebaker: Construction Executive, Speaker & Advocate
I have been doing it for nearly 30 years and I am not slowing down. My career started in commercial roofing sales at Metal-Era, where I took a $350,000 product line to $1.5 million in a single year and trained national sales reps on building envelope systems. That experience showed me what was possible when you combine product knowledge with relentless hustle.
In 2002, I founded Penebaker Enterprises, a commercial roofing and sheet metal fabrication company in Milwaukee. Started with a truck and a phone. Within nine years I grew it to $15 million in annual revenue with 50 employees. Later I scaled Roofed Right America from $5 million to over $35 million, managing 180 employees across five states in the Upper Midwest.
Today I am the Regional General Manager for the Upper Midwest at Great Day Improvements. I oversee four markets: Chicago, Madison, Milwaukee, and Minneapolis. My job is to build the systems and develop the people that turn underperforming branches into top performers.
But work is only part of my story. I am also a national speaker on leadership, resilience, and gun violence prevention. My mother Joyce died by suicide with a gun when I was 20 months old. That loss shaped everything about how I lead, how I show up, and why I refuse to stay quiet on issues that matter.
I have spoken at the Democratic National Convention, been featured in TIME Magazine and Bloomberg, testified before state legislatures, and delivered keynote addresses to audiences of 20,000+. Whether the room is a corporate boardroom or a national convention stage, I bring the same thing: honesty, energy, and a real story.
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, and eventually, something you channel. That loss became the foundation for my work in gun violence prevention advocacy and the reason I speak publicly about grief, resilience, and the cost of inaction.
Founded Penebaker Enterprises
Built a commercial roofing and sheet metal fabrication company from scratch in Milwaukee, Wisconsin. Started with nothing but a truck, a phone, and deep knowledge of EPDM, TPO, and GAF roofing systems. Over nine years I grew Penebaker Enterprises to $15 million in annual revenue with a 50-person workforce. I handled everything from estimating to project management to crew scheduling, learning every corner of the construction business from the ground up.
Scaled Roofed Right America
Took the helm of a $5 million roofing operation and built Roofed Right America into a $35 million company with 180 employees across five states in the Upper Midwest. That growth came from hiring right, building culture, and refusing to cut corners on quality or safety. We earned a reputation for doing the work correctly the first time, and our retention rates reflected it. I managed full P&L responsibility, regional expansion, and a sales organization that consistently outperformed targets.
Featured in BizTimes Milwaukee (2017)
Ran for Congress & National Convention Speaker
Spoke at the Democratic National Convention in Philadelphia and ran for Congress in Wisconsin's 5th District on a platform of gun violence prevention, economic opportunity, and healthcare access. The congressional race put my story in front of millions. I spoke about my mother, about the families destroyed by gun violence every day, and about the political courage it takes to do something about it. I did not win the seat, but I gained a national platform that I have used every day since.
DNC Convention Speaker & Everytown Fellow
Returned to the Democratic National Convention stage, this time speaking to a virtual national audience about my mother, about the cost of gun violence in America, and about what happens when we choose silence over action. That same year I became an Everytown for Gun Safety Wisconsin Fellow, working on state-level advocacy for common-sense gun legislation. I also served as Board President of Planned Parenthood of Wisconsin's C4 organization through 2024.
Chose Family First
Stepped back from board service and political advocacy roles to focus on my mental health and my family. I had been going full speed for years, and something had to give. That decision, choosing rest and presence over public visibility, was the hardest and best call I have made in a long time. It reminded me that the people closest to you deserve the best of you, not the leftovers.
Leading the Upper Midwest
Took on the Regional General Manager role at Great Day Improvements, a national home improvement company. I oversee operations, sales, and team development across four markets: Chicago, Madison, Milwaukee, and Minneapolis. The region needed a turnaround, and that is exactly the kind of challenge I was built for. I am building systems, developing leaders, and creating a culture of accountability and results across every branch.
Where I Am Now
I am engaged to Anne Kirschling. We are getting married in November 2026 at The Gage in West Allis, Wisconsin. I have three kids, Josie, Kyan, and Sydney, and they are the center of everything I do. Being a present father is not negotiable for me, especially given how I grew up without my mother.
Outside of work, I collect sneakers. Nike Air Force 1s, Jordans, Yeezys. I resell, I make TikToks about them, and I have a collection that takes up more closet space than it should. I am a Kendrick Lamar fan, a sports junkie, and someone who believes strongly that you can be serious about your work and still not take yourself too seriously.
I believe in showing up, doing the work, and being honest about the hard stuff. That goes for parenting, for running a business, and for talking publicly about loss, mental health, and what it takes to keep going when things fall apart.
What I Bring to the Table
Construction Expertise
Deep technical knowledge of EPDM, TPO, GAF products, JM insulation systems, and building envelope solutions. Certified in OSHA 10, OSHA 30, and asbestos abatement. Nearly three decades in commercial roofing and sheet metal fabrication.
Scaling Organizations
Proven track record of building and scaling businesses from startup to multi-state operations. Grew Penebaker Enterprises to $15M and Roofed Right America to $35M+. I know how to hire, how to build culture, and how to create systems that sustain growth.
Team Turnarounds
Track record of turning around underperforming teams, branches, and markets across multiple states. I build accountability systems, develop managers, and create cultures where people want to perform. The teams I inherit always look different within 90 days.
National Advocacy
National-level advocacy experience spanning gun violence prevention, election integrity, and healthcare access. Two-time DNC Convention speaker. Everytown for Gun Safety Fellow. I know how to tell a story that moves people to action and how to navigate complex political environments.
Leading Through Adversity
I understand what it means to lead when things are hard, not just when they are easy. Losing my mother at 20 months old, building a business from nothing, navigating a political campaign. Every challenge taught me that resilience is not a personality trait. It is a practice.
Revenue Growth
Full P&L ownership and revenue growth from startup to $35M+. I build forecasting models, manage regional budgets, and create incentive structures that drive performance. Every dollar gets accounted for, and every team member knows what they own.
What I Stand For
Honesty Over Comfort
I say what needs to be said, not what people want to hear. In business and in life, the truth is where progress starts. I have fired people I liked because the team needed it. I have told audiences things they did not want to hear because those things were true. Comfort is not a leadership strategy.
People First
Every company I have built started with the people. Revenue, margins, market share, those are outcomes. The inputs are hiring the right people, training them well, and creating an environment where they want to stay and perform. The numbers always follow when you invest in the team first.
Show Up Anyway
Loss, setbacks, failure. I have been through all of it. My mother's death. A business partnership that went sideways. A congressional race I did not win. The difference between people who make it and people who do not is simple. You keep showing up. That is the only strategy that works long term.
In the Press
Personal Essay on Gun Violence
Published a first-person essay in TIME about losing my mother to gun violence and the cost of political inaction. The piece reached millions of readers and became one of the most-shared personal accounts on the human toll of gun violence in America.
National TV Ad Campaign
Featured in a Bloomberg-funded gun violence prevention ad that aired during the Super Bowl to a national audience of over 100 million viewers. The campaign highlighted personal stories of loss as a call to action for common-sense gun legislation.
National Interview on Election Integrity
Interviewed on CBS News about the fake electors lawsuit and the fight to protect election integrity in Wisconsin. The segment covered the legal challenges to the 2020 election results and the role of state-level advocates in defending democratic processes.
Two-Time Convention Speaker
Addressed the Democratic National Convention in both 2016 and 2020, sharing my story of loss and advocacy on one of the largest political stages in the country. Both speeches focused on gun violence prevention and the personal cost of inaction, reaching tens of millions of viewers.