Fighting for a Fair Chance at Microsoft with Shelley Winner

Shelley Winner is the Founder of Winner’s Circle, a rehabilitative and reentry program designed to empower justice-impacted individuals through mindset training, financial literacy, and sales skills. She was previously a top sales leader at Microsoft, where she rose from an entry-level retail hire to the company’s #1 computer sales rep worldwide, earning the prestigious Gold Club award, an honor achieved by less than 2% of employees. Her advocacy and success directly influenced Microsoft to change its hiring practices, ultimately joining the Second Chance Business Coalition and expanding fair chance hiring across the organization. Today, Winner is a nationally recognized voice for criminal justice reform, using her platform to demonstrate the transformative power of second chances.