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Team
A small, experienced team bringing together social enterprise, recovery-focused workforce development, and mission-driven finance.
Founder & CEO
HighTop Cleaning Services LLC & HighTop Social Enterprises
Oliver founded HighTop to build the structured, supportive workplace he needed early in his own recovery. In long-term recovery himself, he leads HighTop Cleaning Services and HighTop Social Enterprises with a simple conviction: businesses can create lasting, supported pathways into work for people overcoming barriers — and be stronger for it.
“When we invest in stable employment, recovery support, and pathways forward, the impact reaches far beyond the individual — strengthening families, employers, and the long-term health of our communities.”
Sr. Director of Workforce Development & Public Relations
HighTop Social Enterprises · Next Chapter Workforce Development Services
Madison leads workforce development and public relations for HighTop Social Enterprises. Through Next Chapter Workforce Development Services and her workforce development work with Jenna's Promise, she has helped connect Vermonters to sustainable employment backed by wraparound support — pairing jobs with the support people need to keep them.
“This work is about more than helping someone find employment — it's about building systems that reflect the barriers Vermonters are facing.”
Strategic Financial Partner
Warp & Woof · Founder of Working Fields
Mickey provides strategic financial planning for HighTop's mission-driven model through Warp & Woof. He founded Working Fields, a Vermont staffing company built specifically for people in recovery and people with histories of conviction. A person in long-term recovery himself, Mickey has spent nearly two decades helping others find a second chance through work.
“The opportunity now is to build on that foundation in a way that balances mission with strong business fundamentals, allowing it to grow and deliver results.”
We also work alongside recovery, training, and workforce partners across Vermont — see our partners.See our partners →