Job Description

Job Description

Job Description

Description:

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

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