Entrepreneurship Program Director, Founders School - $250,000/year USD

Develop founders, not curricula. Most educators believe high school exists to ready students for what comes next. We believe what comes next begins immediately. Founders School is a four-year secondary institution serving students unwilling to postpone creating meaningful impact until they reach adulthood. These students aren't completing simulated entrepreneurial exercises. They're building actual companies, collaborating with experienced founders, becoming proficient in AI, and addressing real-world challenges. Our expectations are elevated because our students are exceptional: launch a million-dollar enterprise, discover problems deserving solutions, and achieve AI mastery ahead of their adult counterparts. Your responsibility is to ensure that ambition remains viable. You won't deliver classroom instruction or dictate operational strategies for student ventures. Instead, you'll mentor a cohort of emerging founders daily, maintaining their accountability, helping them navigate obstacles, and sustaining momentum when entrepreneurship becomes challenging. You'll recognize when to push them harder, when to offer encouragement, and when to facilitate introductions to appropriate mentors or tools. The curriculum, Entrepreneurs-in-Residence, and founder ecosystem supply the technical startup knowledge. You deliver the structure, expectations, and forward motion that convert capability into achievement. This also represents a chance to contribute to an institution from its inception. As part of our founding team in New York City, you'll influence the culture, operational frameworks, and everyday reality of a school built to transform what secondary education can achieve. Your contributions won't merely affect a single student cohort. They will inform the model for every subsequent Founders School location. If you're passionate about entrepreneurship, confident that rigorous standards drive exceptional performance, and eager to dedicate your expertise to cultivating tomorrow's business leaders, we want to hear from you. What You Will Be Doing Mentor and drive a group of student entrepreneurs through regular 1:1 sessions, daily touchpoints, and collective stand‑ups that ensure continuous, quantifiable advancement. Maintain exceptionally demanding performance standards while delivering the guidance and accountability students require to navigate challenges and continue building. Track student development via FounderOS, recognize when students encounter roadblocks, and facilitate connections to mentors, Entrepreneurs‑in‑Residence, or additional resources that catalyze their advancement. Contribute to establishing the culture, rituals, programming, gatherings, and operational cadence of an elite entrepreneurial secondary school. Accompany students on multiple annual trips while cultivating enduring relationships with founders, investors, business operators, and entrepreneurial families. What You Won’t Be Doing Serving as the lead startup advisor or crafting business strategies for students. FounderOS, Entrepreneurs‑in‑Residence, and guest mentors handle that domain. Conducting conventional academic instruction or evaluating traditional coursework. Tolerating mediocre output from students with the capacity for excellence. Facilitating workshops beyond your specialized knowledge or defaulting to superficial startup guidance. Operating within an inflexible educational bureaucracy where administrative processes obstruct substantive student progress. Entrepreneurship Program Director Key Responsibilities Establish conditions where each student continuously develops as an entrepreneur by integrating superior mentorship, rigorous accountability, strategic relationships, and a culture that transforms driven adolescents into competent founders. Basic Requirements A minimum of 3 years in leadership or high‑impact roles at a startup or rapidly scaling organization. Sound business acumen and the capacity to engage credibly with early‑stage entrepreneurs while understanding when to engage specialized experts. Proven capability to mentor, inspire, and maintain demanding standards with high‑achieving individuals. Regular, practical application of AI to enhance your work's quality and efficiency. Excellent communication and relationship‑development abilities with students, families, mentors, and entrepreneurs. Commitment to full‑time, in‑person work in New York City, including periodic travel during the year. Legal authorization to work in the United States. Nice‑to‑have Requirements Launched or co‑launched a company. Background in coaching, mentoring, or directing programs serving teenagers or emerging adults. An active network including founders, investors, business operators, or mentors. Background in early‑stage ventures where you frequently worked across diverse functional areas. About Founders School Founders School is a four‑year high school built for ambitious students who want to create, build, and solve meaningful problems. The program combines Alpha School's elite academics, real‑world experience, and mentorship from world‑class entrepreneurs around three commitments to every student: Build a million‑dollar business. Identify problems in the world worth solving. Master AI before adults do. This is a place for people who'd rather build the thing than manage the thing. We're hiring the founding team that builds the dream high school for the most entrepreneurial and ambitious students in the country. Launching in NYC Fall 2026. There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you! Working with us This is a full‑time (40 hours per week), long‑term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $125 USD per hour, which equates to $250,000 USD per year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult for more details on this topic. Crossover Job Code: LJ-5825-US-Spotswoo-Entrepreneursh #J-18808-Ljbffr Crossover