Career

30 Years in Construction Leadership

Nearly three decades of building companies, leading teams, and delivering results.
Khary Penebaker speaking at community event with microphone
Current Role

Regional General Manager

Great Day Improvements
November 2025 - Present | Midwest Region

Leading operations across six Midwest markets: Chicago, Madison, Milwaukee, Minneapolis, Cedar Rapids, and Green Bay. Managing Design Consultant hiring and training pipelines, subcontractor recruitment across multiple trades, revenue operations, and weekly performance reporting to division leadership. Building high-performing systems, processes, and teams to drive growth and operational excellence.

6
Markets
Now
Hiring
30
Years Experience

Previous roles

President
Roofed Right America
April 2014 - November 2025

Grew revenue from $5M to $35M with 180 employees across four Upper Midwest markets. Helped position the company for a private equity sale that scaled the platform to $120M across five states with 400+ employees. Launched a sheet metal manufacturing division, earned Drexel Metals certified installer status, and maintained 96% customer satisfaction while improving gross margin by 5 points.

$5M to $35M 180 Employees 4 Markets PE Exit to $120M
Director of Strategic Business Development
Metal-Era, Inc.
September 2011 - August 2013

Doubled Roof Edge Systems sales to a $1.4M+ run rate by expanding distribution channels and strengthening manufacturer rep engagement across commercial roofing and architectural sheet metal lines. Served on the SPRI board and led all edge metal product testing for industry compliance. Rebuilt the distribution network, launched a Certified Contractor Program, and delivered 100+ continuing education presentations to architects and specifiers, increasing product specification rates by 15%.

Sales Doubled to $1.4M+ SPRI Board Rep 100+ CE Presentations
CEO & President
Penebaker Enterprises
January 2002 - January 2011

Founded a commercial roofing and sheet metal fabrication company from scratch. Grew revenue from $1.5 million to $15 million. Managed all aspects of operations -- estimating, project management, field crews, client relationships, and financials. Specialized in EPDM, TPO, and GAF roofing systems.

Built the company with a truck and a phone. Left with a decade of proof that I could build something real.

$1.5M to $15M Founded from Scratch Full P&L

Industry expertise

Commercial Roofing EPDM Systems TPO Systems GAF Certified Building Envelope Sheet Metal Fabrication Project Estimation Subcontractor Development Multi-State Operations Team Building P&L Ownership Turnaround Management Revenue Forecasting Production Scheduling

Certifications & training

OSHA 10-Hour Construction Safety (2x)
OSHA 30-Hour Construction Safety (2x)
Asbestos Supervisor Training
GAF Certified Roofing Contractor
Marquette University High School
University of Wisconsin-Milwaukee

Public service & advocacy

Congressional Candidate, WI-5
Democratic Party
2016

Ran for Congress in Wisconsin's 5th Congressional District as a Democrat, bringing a business leader's perspective to public policy.

DNC Representative, Wisconsin
Democratic National Committee
2017 - 2023

Served as a Democratic National Committee member for Wisconsin, including speaking at the national convention.

Gun Violence Prevention Fellow
Everytown for Gun Safety
Ongoing

Gun violence prevention advocacy rooted in losing my mother Joyce to gun suicide when I was 20 months old.

Board President
Planned Parenthood of Wisconsin C4
2021 - 2024

Led political and advocacy strategy for public health access across Wisconsin.