Midwest Leadership Speaker: Khary Penebaker
TL;DR: Khary Penebaker is a Midwest-based leadership speaker available for keynotes, workshops, and panel discussions across Wisconsin, Illinois, Minnesota, Michigan, Iowa, Indiana, and Ohio. His talks on leadership under pressure, resilience, and team building draw from 20+ years of business ownership and national media experience.
Leadership speaking for the Midwest
The Midwest builds things. Manufacturing, construction, agriculture, healthcare, logistics. These industries run on practical leadership, not corporate buzzwords. Khary Penebaker speaks to Midwest audiences because he is one. He has built and run companies in Wisconsin, managed teams across multiple states, and understands the work ethic and values that define this region.
His keynotes connect with Midwest audiences because they are grounded in real experience. No motivational fluff. No recycled TED Talk material. Khary shares hard-won lessons from growing a commercial roofing company to $35M across five states, managing a four-market region spanning Chicago to Minneapolis, running for Congress in Wisconsin, and turning personal tragedy into national advocacy.
Core speaking topics
- Leadership Under Pressure – Decision-making when the stakes are high and the margin for error is thin. From construction job sites to political campaigns, Khary has led through situations where failure was not an option.
- Resilience and Adversity – How to create teams and cultures that survive setbacks and come out stronger. Based on his experience rebuilding after business loss and personal tragedy.
- Construction Leadership – The skilled trades face a generational talent crisis. Khary brings nearly 30 years in commercial roofing and sheet metal on how to build, lead, and retain skilled teams at scale.
- Gun Violence Prevention – Turning personal pain into public purpose. Khary lost his mother to firearm suicide at 22 months old. His story of channeling grief into action resonates across any industry.
Midwest markets and regions
Khary is based in Pewaukee, Wisconsin, and operates across the Upper Midwest. His commercial roofing and leadership career has taken him through Wisconsin, Illinois, Minnesota, and Michigan. He managed a four-market region spanning Chicago, Madison, Milwaukee, and Minneapolis in a prior leadership role. He now leads the Upper Midwest division of MetalMaster-RoofMaster. Events within a four-hour drive of Waukesha County typically involve no travel costs; air travel is discussed during the booking process.
National engagements are also available. Khary has appeared on Wisconsin Public Radio, PBS Wisconsin, HuffPost, and Urban Milwaukee.
Industries and audiences
Khary has delivered keynotes and workshops for audiences across these sectors:
- Construction and Trades – Industry conferences, safety summits, workforce development programs
- Corporate Leadership – Executive retreats, management training, annual meetings
- Nonprofit and Advocacy – Fundraising galas, board retreats, community events
- Healthcare – Wellness conferences, leadership development, resilience training
- Education – University commencements, faculty development, student leadership programs
- Government and Public Sector – State agency conferences, legislative forums, public safety events
What sets Khary apart
Most speakers fly in, deliver a talk, and fly out. Khary lives in the Midwest. He runs businesses here. He is raising his family here. That connection to the region shows in every keynote because he is not talking about Midwest values from the outside. He is living them.
His combination of entrepreneurial experience (growing companies from startup to $35M+ revenue), political experience (Congressional candidate, DNC representative), media presence (Wisconsin Public Radio, PBS Wisconsin, HuffPost), and personal story creates a speaker unlike anyone else on the circuit.
Book a Midwest speaking engagement
Planning an event in the Midwest? Request availability or call 414-349-5009. Early booking is recommended for peak conference season (September through November and January through March).
Common questions
Do you charge travel fees for Midwest events?
Events within driving distance of Pewaukee, WI (roughly 4 hours) typically have no additional travel costs. For events requiring air travel or overnight stays, travel expenses are discussed during the booking process.
Can you speak at multi-day conferences?
Yes. Khary can deliver a keynote on day one and facilitate a workshop on day two, or participate across multiple sessions. Multi-day engagements are available at a packaged rate.
What size audience works best for your talks?
Khary has spoken to audiences from 20-person executive retreats to 2,000+ conference attendees. The content and delivery style adjust based on audience size and format.
Do you offer virtual speaking options?
Yes. Virtual keynotes and hybrid events are available. Khary has delivered virtual presentations for national organizations and can accommodate remote audiences with professional production quality.
Based in Wisconsin? Visit the dedicated Wisconsin Keynote Speaker page for state-specific information. View all speaking topics.
Last updated: May 31, 2026