Today we’d like to introduce you to Cashmere Bentley.
Hi Cashmere, please kick things off for us with an introduction to yourself and your story.
I came to StepUp in 2020 during the COVID-19 pandemic looking for support after my job permanently closed. I went through the employment readiness workshop and received tremendous support in developing employment skills such as resume creation, answering interview questions effectively, and participating in mock interviews.
After graduating from the program, I began working with my Success Coach, who recognized my abilities and potential as a leader and employee. She advocated for me to become an apprentice at the organization, and that became my entry point into StepUp. I served as an Administrative Apprentice for six months, and during that time I was able to not only learn more about StepUp’s mission, but also gain valuable professional skills that strengthened my job search and career development.
Once my apprenticeship ended, I was offered a part-time position as a Success Coach, where I had the opportunity to work directly with participants who were navigating challenges similar to my own. Since then, I have been honored to serve in multiple roles throughout the organization as I continued to grow and thrive. Today, I am proud to serve as the Executive Director of StepUp Durham.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
As you know, most roads traveled come with bumps along the way. Some of the biggest challenges in my journey came during my transition into the Program Manager role. I was out on maternity leave for six months, and when I returned to the organization, many things had shifted and changed, including the removal of our employment readiness workshop. At the same time, we were transitioning out of the COVID era, and I was tasked with moving our programming from virtual back to in-person services.
Upon my return, I focused heavily on rebuilding staff dynamics, transitioning our programming back to in-person engagement, and relaunching our beloved employment readiness training. None of this was an easy feat, but four years later, I am incredibly proud of our team’s ability to successfully navigate these program changes and continue serving our community effectively.
There was also a significant learning curve during my transition into the Executive Director position. This is my first time serving in a role of this magnitude, so over the past year I have intentionally focused on networking, learning the ins and outs of nonprofit leadership, and ensuring that our organization continues pushing forward and growing stronger.
Appreciate you sharing that. What should we know about StepUp Durham?
StepUp Durham is a workforce development nonprofit dedicated to empowering job seekers in the Durham community who face barriers to employment. We offer free employment readiness training, personalized job coaching, employer referrals, and supportive services designed to help individuals secure and maintain sustainable employment.
The mission of StepUp Durham is to empower job seekers by providing access to opportunity, essential resources, and holistic support that enhances lives and fosters both personal and community growth. Through our programming, we strive to not only prepare participants for employment, but also support them in building long-term stability and confidence.
We are especially proud of our holistic approach to workforce development and the level of preparation, support, and reassurance we are able to offer both job seekers and employer partners throughout the employment journey.
Can you talk to us about how you think about risk?
I believe risk-taking is an important part of growth, leadership, and innovation, especially in nonprofit and community-based work. For me, taking risks does not mean acting recklessly — it means being willing to step into unfamiliar spaces, make difficult decisions, and embrace change even when the outcome is uncertain. I think the most impactful leaders are the ones who can thoughtfully assess risk while still moving forward with courage and purpose.
One of the biggest risks I have taken was stepping into the Executive Director role at StepUp Durham. This was my first time serving in a position of this magnitude, and while I knew I had the passion and lived experience to lead, I also knew there would be a steep learning curve. Taking on the responsibility of leading an organization, managing staff, building community partnerships, fundraising, and ensuring program sustainability was both exciting and intimidating. However, I viewed it as an opportunity to grow personally and professionally while also helping push the organization forward.
Another major risk came during my transition into Program Manager after returning from six months of maternity leave. At that time, the organization was navigating significant programmatic changes due to the transition out of COVID. We were moving programming from virtual back to in-person, rebuilding staff dynamics, and relaunching our employment readiness workshop after it had been removed. There was uncertainty around how participants and staff would adjust, but I knew those changes were necessary to continue serving our community effectively. Looking back, I am proud that we took those steps because they strengthened our programming and organizational culture.
Overall, I approach risk by asking myself whether the potential impact and growth outweigh the fear of failure. I believe some of the greatest opportunities come from stepping outside of your comfort zone, being adaptable, and remaining committed to the mission even during uncertain moments.
Pricing:
- FREE
Contact Info:
- Website: https://www.stepupdurham.org/
- Instagram: https://www.instagram.com/stepupdurham?igsh=YjMxcGtya2h3cXdt
- Facebook: https://facebook.com/StepUpDurham
- LinkedIn: https://www.linkedin.com/company/stepup-durham/posts/?feedView=all
