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Ainsley Castro Charles
National Director, Strategic Partnerships @Yupro Placement
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WORK HISTORY
National Director, Strategic Partnerships @Yupro Placement
I lead national workforce partnerships at YUPRO Placement, working closely with Year Up United, enterprise employers, and external partners to create long-term career pathways for alumni and skills-first talent.My work focuses on helping organizations rethink how they identify, develop, and retain talent while connecting Year Up United graduates and experienced professionals to meaningful career opportunities.I collaborate with workforce leaders, MSP programs, and hiring teams to design sustainable talent pipelines through staffing, apprenticeship pathways, and employer partnerships.How I support organizations• Build long-term pathways for Year Up United alumni and early to mid-career professionals• Partner with enterprise employers and Fortune 500 teams on skills-first workforce strategies• Support hiring through contract, contract-to-hire, and apprenticeship models• Collaborate with MSP and procurement leaders to streamline workforce programs• Connect employers to trained talent across technology, operations, HR, finance, and business rolesAreas of focus• Enterprise workforce partnerships• Skills-first hiring strategy• Year Up United alumni career pathways• MSP and contingent workforce partnerships• Talent pipeline development• Workforce innovation and apprenticeship models
EDUCATION
Bentley University
Bachelor of Science, Finance
Institute for Nonprofit Practice
Core Certificate Program
ABOUT AINSLEY CASTRO CHARLES
Over the years, I’ve had the opportunity to collaborate with Fortune 500 organizations, workforce leaders, and public sector partners who are rethinking how they discover and develop talent.Eight years ago, I made a decision to shift my own career path, and it turned out to be one of the most meaningful decisions I’ve ever made. That experience shaped how I see talent, opportunity, and the impact the right career can have on someone’s life.Since then, I’ve dedicated my work to helping organizations rethink how they discover and develop talent while opening doors for people who simply need the opportunity to show what they can do.At YUPRO Placement, I partner with workforce leaders, hiring managers, and enterprise teams who want to build stronger, more resilient organizations. Many of the conversations I’m part of center on the same challenge: how to grow great teams when traditional hiring models are no longer enough.My work focuses on skills-first hiring and workforce strategies that help organizations identify talent based on capability, potential, and the ability to learn, not just credentials.Over the years, I’ve had the privilege of collaborating with companies across industries who are rethinking how they:• build sustainable talent pipelines• convert early - mid level career talent into long-term contributors• strengthen retention and team stability• invest in talent that might otherwise be overlookedWhat I enjoy most about this work is the relationship side of it. The best workforce strategies aren’t created in isolation. They’re built through honest conversations with leaders who care about their teams, their organizations, and the people whose careers they help shape.My experience spans workforce partnerships, staffing solutions, apprenticeship pathways, and talent pipeline strategy across the U.S, always with the same goal in mind: connecting capable people with meaningful careers and helping organizations build teams that last.If you’re thinking about workforce strategy, skills-first hiring, or new ways to approach talent development, I always enjoy exchanging ideas with others in this space.Outside of work, I’m a wife, a mom, inner city Boston native, and someone who believes that meaningful careers create ripple effects for families and communities.
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