Episode 90: Shelley Winner
- August 24, 2025
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.
“Reentry starts while you’re incarcerated. Prison is the incubation period. That’s when you need to start working on yourself, programming, and learning how to change your thoughts—because if you can change your thoughts, you can change your life.”
In this interview, Shelley shares her extraordinary journey from growing up in a home shaped by addiction to battling her own struggles with substance abuse, incarceration, and federal charges before finding sobriety and purpose. She recounts the turning point of discovering she was pregnant while incarcerated, her persistence in seeking treatment despite systemic barriers, and the faith-driven mindset shift that became the foundation of her recovery. Shelley details the challenges of reentry, including her fight against discrimination during Microsoft’s hiring process and the pivotal role of San Francisco’s Fair Chance Ordinance in securing her first job in tech.
Episode Outline
(00:00:00) Introduction and Shelley’s Early Life in a Home Shaped by Addiction
(00:04:00) Bartending in North Dakota and Returning to Drug Use
(00:06:00) Entering the Drug Trade and Federal Investigation
(00:09:00) Sting Operation, Surveillance, and Arrest
(00:14:00) Jail Time, Detox, and Facing Withdrawal
(00:16:00) Pregnancy, Sobriety, and Turning Toward Treatment
(00:19:00) Fighting for Admission into a Faith-Based Program
(00:21:00) Surrender, Mindset Shift, and Beginning Recovery
(00:24:00) Transition to Reentry and Dreams of Working in Tech
(00:25:00) Microsoft Job Application and Background Check Challenge
(00:28:00) Invoking the San Francisco Fair Chance Ordinance
(00:31:00) Securing the Job and Excelling at Microsoft
(00:33:00) Rising to Top Sales Rep and Winning Microsoft’s Gold Club Award
(00:35:00) Microsoft Changes Hiring Policies and Launches LEAP Program
(00:37:00) Advocacy for Fair Chance Hiring and Broadening Opportunities
(00:41:00) Founding Winner’s Circle: Mindset, Literacy, and Sales Training
(00:44:00) Message to Incarcerated Listeners: Hope, Programs, and Change
(00:45:00) Expanding Winner’s Circle to 25 Prisons Nationwide
(00:46:00) Closing Reflections on the Power of Stories and Programs
With a 75% post-incarceration employment rate and less than 5% recidivism rate, The Last Mile has created a new precedent for job opportunities and sustainable wages for justice-impacted individuals. By giving returned citizens proper training while incarcerated, job search support, and following up with support services, The Last Mile is moving the needle on Fair Chance employment.
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