Vice President of Programs & Training

PLEASE NOTE: We are partnering with On-Ramps to manage hiring for this role. Applications submitted through this portal will not be monitored. Please submit your application directly via On-Ramps here to be considered.

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About the Organization

Short Summary

Pursuit is a pioneering AI-native organization building the nation's premier tech workforce pipeline to unlock lasting economic mobility for low-income and underrepresented communities.

Long Summary

For over a decade, Pursuit has unlocked economic mobility by propelling thousands of adults from low-income backgrounds into high-wage tech careers, taking average starting incomes from $17K to $94K and generating nearly $1B in lifetime wage gains. We've also pioneered the Pursuit Bond, an innovative outcomes-based financing model that aligns investor returns with long-term economic mobility, allowing us to scale impact in a financially sustainable way.

Now, as AI reshapes the global economy, Pursuit is pioneering the nation's premier AI-Native workforce pipeline. We are transforming how economic opportunity works at scale through a rigorous, full-funnel training model combining in-person collaborative learning, real-time curriculum adaptation, and deep employer integration.

Powered by $20M in scale funding from organizations like Google, Anthropic, Adobe, Blackstone, Robin Hood and others, Pursuit is building a roadmap of growth to directly train thousands of more Americans and to build enduring workforce training solutions that can support the ecosystem at large.

About the Position

What You'll Do

As AI reshapes the global economy, workforce development stands at a historic inflection point. Pursuit is seeking a visionary, outcomes-obsessed Vice President of Program and Training (VPPT) to lead and scale our groundbreaking AI-native training program. This role offers an unprecedented platform to architect workforce strategy, expand a proven economic mobility engine, and build the foundation for the upcoming AI Jobs Institute to serve thousands of Builders. Reporting to the CEO, the VPPT will serve as the chief architect and operator of the training and job readiness lifecycle. You will have end-to-end ownership across recruitment, community partnerships, persistence, AI-driven curriculum, and candidate-side job readiness. Leading a rapidly expanding multidisciplinary team, you will combine private-sector operational rigor with a deep commitment to human flourishing.

This is an invitation to solve one of the nation's most urgent workforce challenges. As VPPT, you will act as a national spokesperson and subject matter expert, setting the bar for what it means to build sustainable, scalable pathways into the future of work while ensuring underrepresented communities lead the AI revolution.

Key responsibilities include but are not limited to:

Program Vision, AI Pedagogy & Scalable Architecture

• Own the overarching vision, pedagogy, and architecture of Pursuit's AI-native training programs.
• Define and iterate on the curriculum, instructional design, and skill-acquisition model to reflect an evolving AI labor market.
• Establish replicable program delivery frameworks designed to rapidly scale capacity toward thousands of Builders annually.
• Define job-readiness standards for AI-adjacent roles in close alignment with employer expectations and labor market signals.
• Drive continuous pedagogical improvement using real-time performance data, Builder feedback, and industry trends.
• Partner with Product and Engineering to integrate Pursuit's AI-powered learning platform directly into the program model.
• Explore advanced growth models, including the licensing, franchising, or institutionalization of the AI Jobs Institute.

Full-Funnel Enrollment, Persistence & Builder Success

• Own the complete enrollment funnel, from community outreach and recruitment strategy through selection and onboarding.
• Build and manage strategic partnerships with community-based organizations, local institutions, and referral networks.
• Utilize data-driven recruitment campaigns to consistently meet cohort volume and quality targets for low-income Builders.
• Own Builder retention and persistence as core metrics, establishing early-warning systems and proactive intervention structures.
• Oversee the end-to-end Builder experience, cultivating a high-bar environment that balances rigorous challenge with support.
• Integrate industry leaders, volunteers, and corporate partners into fireside chats, capstone projects, and Demo Days.
• Maintain a relentless focus on final employment outcomes, ensuring tight alignment with candidate-side job placement teams.

Team Leadership, Operational Rigor & Scaling

• Cultivate a high-accountability culture driven by an obsession with outcomes, operational precision, and human flourishing.
• Oversee flexible program delivery schedules that accommodate non-traditional hours, including evenings and weekends.
• Establish robust operating infrastructure, including forecasting models, KPI frameworks, and data-driven team rhythms.
• Manage team operational performance to maintain consistency, quality, and strict standards across all program touch points.
• Model AI-native workflows by directly implementing AI tools, automated processes, and tech infrastructure across team operations.

Strategic Leadership, Thought Leadership & Ambassadorship

• Serve as a core member of the executive leadership team, shaping Pursuit's national expansion and growth strategy.
• Act as an internal and external spokesperson on what it takes to train, upskill, and place AI-native talent at scale.
• Synthesize program insights and workforce data to position Pursuit as a national authority on AI workforce development.
• Represent the program at milestone events, national conferences, and high-profile meetings with funders and partners.
• Collaborate closely with the CEO and Chief Product Officer to align program direction with market demands and funding opportunities.

Who You'll Work With

You will report to the Chief Executive Officer. You will build, manage, and hold accountable a multidisciplinary team growing from 10 to 25+ members over the next year.

Required Skills and Experience

• 12+ years of professional experience in fast-paced, outcomes-driven environments, with at least 5 years managing teams of 10+ people (ideally including managers of managers).
• Demonstrated success owning end-to-end program/project outcomes, ideally including community outreach, partner development, enrollment targets, retention, skill acquisition, and final job placements.
• Experience designing, shaping, and architecting learning models or programs at a curriculum or institutional level to ensure pedagogical rigor at scale.
• Proven track record of fostering critical thinking, professional behaviors, and applied technical skills in real-world, workforce, or adult-learning contexts.
• Skilled people leader adept at evaluating work quality against high standards, offering direct constructive feedback, building accountable teams, and developing talent in dynamic environments.
• Proficient in using data and building forecasting models to track KPIs, predict funnel metrics, surface risks, and drive ongoing program optimization.
• Scrappy, hands-on approach with the ability to thrive in ambiguity and actively implement (not just theorize) AI tools and tech infrastructure to improve daily team workflows and processes.
• Deeply motivated by Pursuit's mission of economic transformation through equity, tech access, and expanded opportunity for low-income and underrepresented communities.

Compensation

The salary range for this role is $240,000–$265,000 base, with the ability to earn up to $300,000 based on performance bonus, and a full benefits package.

The compensation above reflects the expectations laid out in this 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 posting. If that ends up being the case, the updated salary range will be communicated to you as a candidate.

Additional Details

Location and Work Environment

This role is based in New York City and operates in an on-site/hybrid capacity. To build authentic relationships with Builders, observe instructional delivery, and provide real-time coaching to program teams, the VP of Programs & Training is expected to be on-site 4 to 5 days per week (including core staff days Tuesday through Thursday).

Schedule and Availability

This role requires flexibility to support programs that run on evenings and weekends (Saturday and Sunday from 10:00am to 5:00pm ET and Monday through Wednesday 6:30pm to 10:00pm ET). The VPPT is not expected to be on-site for every class, but must maintain flexibility to support off-hours operations, manage staff on non-traditional schedules, and participate in key programmatic milestones.

On average, candidates can expect 1 to 2 off-hours events or observations per week (averaging about 20 to 23 per quarter). In addition, as the VP of Programs & Training works to support Builders during these key programmatic hours, they may adjust their schedule as appropriate as long as they maintain outcomes. Key touch points include:

• Program Milestones & Capstones: Attending monthly evening hackathons, weekly Tuesday evening fireside chats (6:30pm–8:00pm), and major quarterly Demo Days or class launches.
• Instructional Observation: Periodically dropping into day, evening, or weekend classes to evaluate pedagogy, provide direct feedback to instructors, and connect with Builders.
• Community & Applicant Engagement: Selectively attending evening or weekend information sessions and recruitment workshops to observe staff and engage prospective applicants.

Benefits

• Full benefits package including vision and dental
• Unlimited PTO, plus an all-Pursuit summer break (last week of August) and a week-long holiday break (last week of December)
• 401k match
• Hybrid and flexible work policy with flexible hours
• Dedicated time to build in AI and develop your own AI skills
• Catered lunches once a week and snacks

Equity at Pursuit

We prioritize the richness of diversity across all categories. We welcome new perspectives and make employment decisions 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.

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PLEASE NOTE: We are partnering with On-Ramps to manage hiring for this role. Applications submitted through this portal will not be monitored. Please submit your application directly via On-Ramps here to be considered.