Co-CEO, REACH Pathways in Chicago, Illinois at Reach Pathways L3C

Co-CEO, REACH Pathways
Location: Remote (Hybrid if in Chicago) | Full-time | Reports to: Board of Directors

About REACH Pathways

REACH Pathways™ is the award-winning platform reimagining how young people explore careers, build skills, and connect with opportunity. Recognized by Fast Company’s World Changing Ideas, SXSW Pitch, Chicago Innovation Awards, and others, REACH is preparing the next generation for a workforce transformed by AI, automation, and a generational divide.

Built with and for learners, REACH delivers career guidance personalized by AI, structured skill-building, and near-peer mentorship to drive long-term success. Backed by 30 years of proven outcomes through Chicago Scholars, REACH serves under-resourced students across 40+ states and is rapidly scaling through partnerships with colleges, employers, nonprofits, and school districts.

The Opportunity

REACH is seeking a visionary Co-CEO to help lead our next stage of growth. You’ll join a company with a 12-month+ runway, rapid user growth (2,000+ and rising), strong partner traction, and exceptional user feedback (including a 70% retention rate and 20% referral rate). You will share executive leadership alongside our current Co-CEO and Co-Founder and be directly responsible for business growth, go-to-market strategy, product-market fit, and investor relations.

This is a rare opportunity to co-lead a mission-driven, revenue-generating edtech startup with national momentum, a differentiated product, and a deep commitment to under-resourced youth.

Key Responsibilities

Market Leadership & Growth

• Own and lead go-to-market strategy across multiple verticals: employers, colleges, nonprofits, and school districts
• Drive and close new business deals to grow ARR across revenue streams including licensing, partnerships, sponsorships, and job placement
• Deepen product-market fit through user and partner feedback loops

Fundraising & Investor Relations

• Lead the next investment round (pre-Series A), working closely with advisors and current funders
• Cultivate investor relationships, manage data room and diligence, and provide regular investor updates

Strategy & Execution

• Make core business decisions on product direction, pricing, operations, and scaling strategy
• Maintain alignment with REACH’s mission, values, and impact goals in alignment with the mission, values, and impact goals of Chicago Scholars, while ensuring a sustainable profitable business model
• Co-lead quarterly planning and OKR processes with executive team

Leadership & Culture

• Manage a growing cross-functional team (product, tech, employability, operations)
• Serve as co-leader of the company, building a strong, mission-aligned, and accountable culture
• Lead board meetings, strategic planning, and organizational pivots when necessary

The anticipated salary range for the role is $175,000-$190,000 with a short- and long-term bonus structure and competitive benefits.

Who You Are

Must-Have Experience

• 10+ years in edtech, youth development, workforce development, or adjacent fields
• Proven experience leading a high-growth startup or early-stage company (CEO, GM, or senior exec role)
• Demonstrated ability to raise capital from institutional or mission-aligned investors
• Track record of selling to education systems, employers, or public/private sector partners

What You Bring

• Strategic thinker who thrives in ambiguity, adapts quickly, and makes data-informed decisions
• Mission-first leader who deeply understands the challenges facing under-resourced youth
• Passion for building tech that drives equity, opportunity, and long-term impact
• Clear communicator and inspiring storyteller who can galvanize funders, partners, and team members
• Strong understanding of edtech, AI’s implications on work, and the future of learning
• Proven track record in product sales and revenue growth

Why Join REACH

• Join a fast-scaling, award-winning company redefining access to opportunity
• Lead with purpose—and results—with a model backed by decades of research and impact
• Work with a team that believes in bold moves, not small tweaks
• Shape the future of college and career readiness, equity in AI, and youth-centered innovation