Chief AI Programs & Training Officer

On-Ramps; New York (NY); On-site; USD 180,000 - 260,000; Full time

Job summary

Pursuit in New York City is seeking a visionary, outcomes-obsessed Vice President of Program and Training (VPPT) to lead and scale our AI-native training program. You will own end-to-end recruitment, partnerships, curriculum, and candidate readiness, while guiding a multidisciplinary team toward thousands of Builders annually.

Based on-site with hybrid options, this role demands 12+ years of experience, a proven track record in program delivery, data-driven improvements, and a deep commitment to

Qualifications

• 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).
• Experience 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.

Responsibilities

• 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.
• 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.

Skills

Team leadership

Program management

Curriculum design

Data-driven decisions

Stakeholder engagement

AI pedagogy

Job description

Pursuit in New York City is seeking a visionary, outcomes-obsessed Vice President of Program and Training (VPPT) to lead and scale our AI-native training program. You will own end-to-end recruitment, partnerships, curriculum, and candidate readiness, while guiding a multidisciplinary team toward thousands of Builders annually.

Based on-site with hybrid options, this role demands 12+ years of experience, a proven track record in program delivery, data-driven improvements, and a deep commitment to