Experience

Nearly 30 years of building.

From sales floors to rooftops to boardrooms. Every role taught me something about leadership, accountability, and what it takes to build something that lasts.

2026 - Present
Division President
MetalMaster-RoofMaster

I am Division President of MetalMaster-RoofMaster, the Upper Midwest commercial roofing and architectural sheet metal division of Wolkow Braker Roofing Corp., based in McHenry, Illinois. It is a 49-year-old company, now employee-owned through a new ESOP, in the middle of a real rebuild. It has a rich history and an incredible amount of capacity, like a caged animal that just needs to be unleashed. That is what I am here to do, and I love this job. I have not been able to say that in a long time.

Khary Penebaker professional headshot
30+
Years in commercial roofing
McHenry, IL
Headquarters
2025 - 2026
Regional General Manager
Great Day Improvements

I ran Great Day Improvements' Upper Midwest region, the three-season sunroom division across Chicago, Madison, Milwaukee, and Minneapolis. I inherited a region with real problems, falsified records, staff resignations, and quality issues, and started rebuilding it from the ground up. A few months in, a Chicago opportunity pulled me to MetalMaster.

Khary Penebaker professional headshot
4
Markets
3
States
2014 - 2025
President
Roofed Right America

I took over a roofing company, renamed it Roofed Right America after a trademark fight, trademarked it, and grew it from about $5 million to $35 million with a team of 180 across the region. When it sold to private equity, we stopped seeing eye to eye. I value my mental health more than a paycheck, so I resigned at the end of October 2025. I lost a dear friend over that disagreement, someone I still miss to this day.

Roofed Right America team in front of company trucks
Roofed Right America team
$35M
Revenue
180
Employees
2011 - 2013
Director of Product Management & Strategic Business Development
Metal-Era

At Metal-Era I learned the technical side of this industry, how edge metals are tested and how building codes get made, and I worked with the Canadian government to help develop codes that lined up with ours. I fell in love with sheet metal here. I also got let go. After ten years running my own company, I was not very manageable yet, and I can own that now.

2002 - 2011
CEO & President
Penebaker Enterprises

On January 1, 2002, I started my own company out of my garage with nothing and built it into one of the top five roofing firms in Wisconsin, union sheet metal and union roofing both. When the recession reached commercial roofing in 2009 and 2010, customers paid far slower than our contracts said. I burned through my reserves and my line of credit, and it ended in an involuntary Chapter 7 liquidation in 2011. I did not run from the debt and I did not hide from it. I damn near lost everything, including the value of my name, and I learned more in that failure than I could have any other way.

Young Khary Penebaker in Penebaker Enterprises polo
Penebaker Enterprises, early days
Top 5
Roofing firms in WI
2002
Built from a garage
2016 - 2023
Civic Leadership
DNC / Congressional Campaign

I ran for Congress in Wisconsin's 5th District in 2016. I served as DNC Representative for Wisconsin from 2017 to 2023 and on the executive board of the Wisconsin Democratic Party, was Board President of Planned Parenthood of Wisconsin C4 from 2021 to 2024, and an Everytown for Gun Safety fellow. I also served as a Biden elector, and stepped back after the death threats that followed.

Khary Penebaker with Vice President Joe Biden and Senator Tammy Baldwin
With Vice President Biden and Senator Baldwin
Credentials

Professional certifications

OSHA 10-Hour Safety Training
Completed twice
OSHA 30-Hour Safety Training
Completed twice
Asbestos Supervisor Training
EPA / State-Accredited
GAF Certified Roofing Contractor
GAF Materials Corporation
BizTimes Master Mettle Award
BizTimes Milwaukee, 2017
Areas of expertise

What I know best

Leadership Under Pressure Scaling Construction Companies Commercial Roofing & Sheet Metal Home Improvement Operations Gun Violence Prevention Resilience & Team Building Workforce Development Skilled Trades Corporate Culture Accountability Systems P&L Management Multi-State Operations

That is the arc.
The rest is the story.

If you want the whole picture, in my own words, read my story.

Read my story