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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

Starting April 27, 2026 as Division President of MetalMaster-RoofMaster, the Wolkow Braker Roofing platform's Upper Midwest commercial roofing and architectural sheet metal division. Headquartered in McHenry, Illinois.

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

Led four markets across the Upper Midwest: Chicago, Madison, Milwaukee, and Minneapolis. Inherited a region with significant challenges, falsified records, staff resignations, and quality issues, and began rebuilding from the ground up.

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

Grew revenue 5X from $6M to $30M+ by capturing federal, state, and private contracts across five states. Led 180 employees, built estimating systems securing $5-10M in yearly bookings, and delivered $100M+ in cumulative sales.

Roofed Right America team in front of company trucks
Roofed Right America team
$100M+
Cumulative Sales
180
Employees
5
States
2011 - 2013
Director of Product Management & Strategic Business Development
Metal-Era

Doubled Roof Edge Systems sales past a $1.4M run rate. Rebuilt distribution network, launched a Certified Contractor Program lifting channel revenue 18%, and delivered 100+ CEU courses to architects.

2X
Sales Growth
18%
Channel Revenue Lift
2002 - 2011
CEO & President
Penebaker Enterprises

Founded and scaled Wisconsin's largest minority-owned roofing firm to $15M annual revenue with 50 union craftworkers. Achieved 23% net margin and captured 75% of public sector share through DOT, state, municipal, and educational contracts.

Young Khary Penebaker in Penebaker Enterprises polo
Penebaker Enterprises, early days
$15M
Revenue
50
Employees
2016 - 2023
Civic Leadership
DNC / Congressional Campaign

Ran for Congress in Wisconsin's 5th District in 2016. Served as DNC Representative for Wisconsin from 2017 to 2023. Board President of Planned Parenthood of Wisconsin C4 (2021-2024) and Everytown for Gun Safety Wisconsin Fellow.

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

Real experience.
Real stories.

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