Build Your Career with Winning Hand

Join a team that values craftsmanship, integrity, and professional growth. We're always looking for talented individuals to help us serve our community.

Why Join Our Team?

Competitive Pay

Industry-leading compensation packages with performance bonuses and regular raises for top performers.

Flexibility

Flexible scheduling options and work-life balance that fits your lifestyle. We understand the importance of family and personal time.

Training & Development

Ongoing training programs, certifications, and skill development to advance your career in the industry.

Company Paid Trips/Events

Enjoy team-building trips, company events, and celebrations. We reward hard work with memorable experiences.

Modern Technology & CRM

Work with cutting-edge technology and CRM systems that make your job easier and more efficient.

Career Growth

Clear advancement paths from entry-level to leadership positions. We promote from within whenever possible.

Open Positions

Explore opportunities to join our growing team

Sales Representative

Join our high-performing sales team! Generate leads and close deals for residential and commercial roofing projects. Earn uncapped commission with performance bonuses and target-based incentives. Top performers consistently earn $100K+.


  • Uncapped commission structure
  • Performance bonuses & monthly incentives
  • Leads provided + self-generated opportunities

Commission Only

$100K+ Potential

IN, KY, TN

Uncapped Commission

Bonuses & Incentives

Sales Manager

Lead and mentor our sales team while closing your own deals. Build and manage a high-performing sales department. Earn uncapped commission on personal sales plus team override bonuses. Proven managers regularly exceed $100K+ annually.


  • Uncapped personal commission + team overrides
  • Leadership bonuses & performance incentives
  • Build and lead your own sales team

Commission Only

$100K+ Potential

IN, KY, TN

Uncapped Commission

Bonuses & Incentives

Apply Today

Take the first step towards joining our team. Fill out the form below and we'll be in touch.

Contact Us

Resume Required

Please email your resume to info@winninghandroofing.com and mention your name in the subject line.


We'll review your application and resume together and reach out within 2-3 business days.