Nonprofit Board Member, Workforce Development (Volunteer)

This is a volunteer governance role on our Board of Directors, not an employment position.

re:WORK TRAINING is looking for a board director who has spent a career inside workforce development. Someone who has scaled a sector-based training organization or helped reform how a public workforce system delivers. Here is why we need that voice now.

WHY THIS SEAT, NOW

Our current board brings real strength: entrepreneurial instinct, deep go-to-market and sales enablement expertise, and strong employer and capital networks. It moves fast and backs new ideas. What we don't yet have is a voice that knows the workforce development field from the inside.

The timing matters. The entry-level tech sales role we train for is genuinely changing. 36% of B2B software companies cut SDR/BDR headcount in 2025 alone, and the promotion rate from SDR to Account Executive has fallen from 34% to 16% in recent years as AI absorbs more of the manual prospecting work. The role isn't disappearing. It is bifurcating and rising in skill. We want a workforce development voice at the table as we adapt to that shift, not after.

WHO WE ARE

re:WORK TRAINING is a Chicago-based 501(c)(3) that trains people for careers in tech sales (BDR and SDR roles) through a free, competency-based program built on a registered apprenticeship standard with the U.S. Department of Labor. We treat the job search itself as the first sales campaign: candidates learn by doing, prospecting real professionals and building real pipelines before they ever interview.

We are a team of seven, working against interest that ran into the thousands last year. Our goal is 120 people hired this year. Through the first half we are at 38 hired with 5 more pending, and our graduates start at an average salary of more than $76,000. We are privately funded and do not rely on government dollars.

WHAT YOU'D HELP US DO

• Help us speak credibly to the private and philanthropic funders we want to reach, in the language the workforce development field actually uses
• Co-develop our next three-to-five-year strategic direction, benchmarked against organizations doing this work well
• Spot the blind spots a sector-literate funder or peer would quietly notice, before they become costly missteps
• Help us understand where we stand next to organizations like Year Up United, Per Scholas, and Merit America, and what it would take to belong in that conversation

WHAT WE'RE LOOKING FOR

• You have personally scaled a workforce development organization across multiple sites or cities, or helped reform how a public workforce system operates. Not just run a single program.
• You are bilingual in the way this role needs: comfortable in a room with a VP of Sales or a CRO, and just as comfortable with philanthropic program officers and workforce boards
• You are a yes-and collaborator. You help us figure out how to do something new inside the norms of this field, rather than telling us that's not how it's done
• You are fluent in the vocabulary funders expect: career pathways, sector strategies, credential attainment, outcomes-based measurement
• Bonus: you have watched how your field is adapting to AI. Not as a technologist, but as someone who has seen the language and models shift in response.
• Chicago-based or willing to be in person is a plus, though not a requirement

THE COMMITMENT

This is a full voting board seat with a 2-year renewable term. Rather than a vague ask to "be on our board," you would come in with one to three specific, named priorities for your first year, agreed on together up front, so you know exactly what a strong year looks like.

NEXT STEPS

If this sounds like you, or like someone you know, reach out to Shelton Banks, at View email address on click.appcast.io to start a conversation. No commitment required to talk it through.