Head of AI Fellowship

About Pursuit

Pursuit is a social impact organization building the future of economic mobility in the age of AI. For over a decade, we’ve transformed lives through immersive training programs that propel adults from low-income backgrounds - often without college degrees - into high-growth tech careers. Our graduates have already generated nearly $1 billion in lifetime wage gains.

Now, as AI reshapes every industry, Pursuit is evolving into an AI-native organization. We’re training AI-native talent, embedding AI into our operations, and building scalable software to extend our impact. From grassroots partnerships to national policy (like our Good Jobs Guarantee), we’re not just filling jobs - we’re rethinking how economic opportunity works at scale.

About the Role

Pursuit is hiring a Head of AI Fellowship to lead and evolve our AI-Native training program that prepares underserved adults for meaningful, well-paid work in an AI-shaped economy. This role oversees the delivery, performance, and continuous improvement of the Fellowship, owning day-to-day execution of programs and performance of the teams that deliver them, while also helping build the team, systems, and program foundations needed to scale toward our goal of serving 2,000 Builders over the next five years through the launch of the AI Jobs Institute.

Reporting to the Chief Operating Officer, you’ll lead a five-person team responsible for program execution and outcomes, balancing people leadership and operational excellence with thoughtful tradeoffs across capacity, quality, and outcomes to ensure the program delivers results today while building toward long-term scale.

Schedule & Availability:

This role requires flexibility to support programs that run on evenings and weekends (Saturday–Sunday 10:00am–5:00pm and Monday–Wednesday 6:30pm–10:00pm). The Head of Program is not expected to be present for all sessions, but must be available to manage staff on this schedule, attend key milestones, and step in to shadow or cover facilitation as needed.

What You’ll Do

• Own and ensure Builder job readiness in an AI-shaped economy, including how readiness is measured and how the Fellowship supports Builders to successfully enter and succeed in high-quality, well-paid roles.
  
  
• Lead the delivery and performance of the program, owning performance against KPIs such as attendance, task completion, and learner work quality, and using insights to continuously improve program design.
  
  
• Manage and develop a five-person team across facilitation, operations, and community engagement, setting a high bar for performance, accountability, and culture.
  
  
• Ensure program excellence in delivery and operations by building strong systems, processes, and tools, and fostering a data-driven culture across the program team.
  
  
• Oversee the Builder experience and program culture, ensuring alignment with Pursuit values and delivering an industry-informed, high-bar learning environment.
  
  
• Track and forecast Builder progress and completion, using those insights to surface risks to executive team, inform decisions, and keep the program on track against targets.
  
  
• Provide structured product feedback to Pursuit’s AI-powered learning product, representing program and Builder needs to improve the experience and effectiveness for both learners and staff.
  
  
• Oversee structured industry engagement, ensuring leaders from industry are integrated into the program with clear purpose, guidance, and operational consistency.
  
  
• Establish the operating foundations needed to scale programs reliably over time, balancing consistency with continuous improvement.
  
  
• Represent the program internally and externally, serving as the face of the Fellowship at milestone moments (e.g., Hackathons, Demo Day) and with hiring partners, funders, and community organizations.

Schedule & Availability:

• 10+ years of overall professional experience in fast-paced, outcomes-driven environments, with at least 3 years managing teams of 5+ people.
  
• Demonstrated experience leading teams toward operational excellence, including the ability to define clear KPIs, build systems and processes, and use data to manage toward targets.
• Experience using data and creating excel models to forecast against goals, track progress and inform continuous improvement.
• Experience evaluating product or work quality against a high bar, providing direct, constructive feedback while maintaining high expectations for quality and outcomes.
  
• Proven problem-solver with a scrappy, hands-on mindset, comfortable operating in dynamic environments and adapting to evolving program needs.
• Experience supporting the development of critical thinking and professional skills in applied or real-world contexts.
• AI-Curious, you understand the impact of AI on the workforce and are excited about its potential for economic mobility, and have experimented with AI tools or simple projects beyond GPTs.
• Mission-Driven, you care deeply about equity, tech access, and expanding opportunity for underrepresented communities.

Pursuit Offers: 

• An opportunity to work at the intersection of tech and social impact, and make a direct impact on the communities of those we serve.
• Competitive compensation in base, plus bonus and a full benefits package
• 401k Match
• Unlimited PTO and an all-Pursuit summer break the last week of August and a week-long holiday the last week of December
• Monday and Friday work from anywhere policy
• Catered lunches once a week and delicious snacks
• Dedicated time to build in AI and hone your AI skills

Salary: 

The expected salary range for this role is $140,000 - $160,000 base.

Pursuit values diversity: 

Our team has a wide range of backgrounds and experiences, and we value the richness that diversity brings to our organization. We welcome new perspectives and affirm that all employment decisions are made without regard to race, color, ancestry, religion, national origin, age, familial or marital status, sex, sexual orientation, pregnancy, gender identity or expression, disability, genetic information, veteran status, or any other classification protected by federal, state, or local law. Pursuit is an equal opportunity employer.