Instructor & Program Manager

About Pursuit

Pursuit is a social impact organization building the future of economic mobility in the age of AI. For over a decade, Pursuit has created life-changing outcomes through training programs for adults from low-income backgrounds, especially those without college degrees. Our graduates have already generated nearly $1 billion in lifetime wage gains

Now, as AI reshapes the future of work, Pursuit is evolving as a leader at the intersection of AI, jobs, economic opportunity, and tech innovation. We’re becoming an AI-native organization: training AI-native talent, embedding AI across our operations, and building software to scale 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.

AI-Native Program Manager

About the Role

Pursuit is hiring an AI-Native Program Manager to own the Builder experience for our nights and weekend cohort in our AI-native program. This role sits at the intersection of coaching, operations, community, and AI systems-building.

You'll support a cohort of high-potential adults from low-income backgrounds (18+) as they build AI fluency, sharpen critical-thinking skills, and unlock pathways into high-paying, career-advancing jobs. But this is not a traditional teaching role. You'll be responsible for designing and continuously improving the systems, workflows, and experiences that help Builders persist, grow, and succeed.

You'll coach Builders, lead workshops, identify operational bottlenecks, build AI-powered solutions, and help shape how Pursuit delivers AI-native workforce development at scale. We're looking for someone who naturally asks: "How could this work better?" - and then prototypes the answer.

As a key member of our team, you'll report directly to the COO and be accountable for cohort outcomes, Builder persistence, operational excellence, and innovation across the learning experience.

This is an onsite, full-time role in our Long Island City office with the following schedule:

• Saturday/Sunday: 9am–5pm

• Monday/Tuesday/Wednesday: 2pm–10pm

(Classes run Sunday/Monday 10am–4pm and Monday–Wednesday 6:30pm–10pm; many of our Builders have family care responsibilities or full-time jobs during the day with limited flexibility.)

About You

You're an operator who loves people.

You might come from startups, customer success, hospitality, workforce development, community operations, learning and development, founder/early-stage roles, or another fast-paced environment where outcomes and relationships both mattered. You know how to create momentum, build trust, and keep people moving through ambiguity.

You're also deeply curious about AI and enthusiastic about using it in your own work. You don't just talk about AI - you use it to automate tasks, improve workflows, create tools, analyze information, and move faster. You enjoy experimenting, prototyping, and sharing what you learn with others.

Most importantly, you believe one of the best ways to prepare people for the future of work is to model an AI-first mindset: treating problems as opportunities to design systems, workflows, and tools that create leverage.

You bring empathy, urgency, creativity, and accountability to everything you do.

Key Responsibilities

Own Builder outcomes

• Serve as the primary operator and coach for a cohort of Builders, responsible for persistence, engagement, completion, and long-term career outcomes.

• Build strong 1:1 relationships with Builders and proactively support them through challenges, setbacks, and career transitions.

• Track performance and engagement data, identify at-risk Builders early, and coordinate interventions to keep people on track.

Lead high-impact learning experiences

• Lead workshops, discussions, and hands-on sessions that are practical, energetic, and rooted in real-world AI applications.

• Create experiences that help Builders develop confidence, agency, and problem-solving skills - not just technical knowledge.

• Model effective AI usage live: prompting, debugging, researching, building workflows, and using AI to accelerate learning and work.

Build and scale an AI-Native program

• Continuously identify opportunities to improve Builder outcomes, coaching quality, operational efficiency, and the learner experience through AI, automation, and systems thinking.

• Design and build lightweight tools, agents, automations, workflows, and internal systems that create leverage for Builders, facilitators, and the broader organization.

• Rapidly prototype ideas, measure impact, and scale successful solutions that improve personalization, reduce manual work, and increase program effectiveness.

Partner on product and innovation

• Serve as a power user and strategic partner for Pursuit's AI training agent and related products.

• Identify gaps in the learner experience, prototype solutions, test new capabilities with Builders, and provide actionable feedback to the product team.

• Represent both learner and operator needs in the evolution of Pursuit's AI-enabled learning ecosystem.

Represent Pursuit externally

• Facilitate workshops, info sessions, and events for prospective Builders, corporate partners, and nonprofit stakeholders.

• Act as an enthusiastic ambassador for Pursuit's mission and AI-native approach to economic mobility.

Ideal Experience

• 4-6 years of professional experience in startups, operations, customer success, workforce development, hospitality, education, learning and development, community operations, or other fast-paced, outcomes-driven environments.

• Proven ability to lead groups, coach individuals, and create momentum in high-accountability environments.

• Demonstrated experience using AI tools to improve workflows, solve operational problems, create learning experiences, or build products.

• Comfortable building lightweight automations, agents, workflows, dashboards, or internal tools using AI.

• Strong systems thinker who naturally looks for ways to create leverage through process improvement, automation, and technology.

• Excellent problem-solving and critical-thinking skills, with the ability to model and coach those skills for others.

• Data-driven and outcomes-oriented, comfortable using metrics to guide decisions and improve results.

• Highly organized, adaptable, and solutions-oriented, with the ability to thrive in ambiguity and rapidly changing environments.

• Strong relationship-builder who can balance empathy and accountability while fostering trust and persistence.

• Deep belief in human potential and the conviction that with the right support and expectations, people can achieve extraordinary growth.

• Enthusiastic adopter of emerging technologies, with a track record of rapidly learning, testing, and operationalizing new tools.

• Passionate about expanding economic opportunity and increasing access to technology and career pathways for historically underserved communities.

What Success Looks Like

In this role, success means:

• Builders persist, grow, and achieve strong career outcomes.

• The cohort culture is ambitious, supportive, and deeply engaged.

• Operational friction decreases because you build smarter systems and workflows.

• AI is visibly embedded in how the program operates, not just what it teaches.

• Builders leave not only with AI skills, but with the mindset and habits of AI-native professionals.

Why This Role Matters

Pursuit exists to create economic transformation through technology and community. As an AI-Native Program Manager, you'll help define what workforce development looks like in the age of AI - not by theorizing about the future, but by building it alongside the people we serve.

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
• Catered lunches once a week and delicious snacks
• Dedicated time to build in AI and hone your AI skills

Salary & Benefits:

The expected salary range for this role is $100,000 - 115,000 base + incentive compensation.

The compensation above is for the expectations as laid out in the job description, however, we are often open to a wide variety of profiles and recognize that the person we hire may be less experienced (or more senior) than this job description as posted.  If that ends up being the case, the updated salary range will be communicated to you as a candidate.

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.