Head, AI Engineering

About the Role

We are looking for a visionary, results-driven Head of AI Engineering to join our Technology leadership team and power the next generation of education. In this role, you will lead the strategy, architecture, and deployment of modern AI technologies across our network. You will build and manage an agile team of AI software engineers to ship high-impact, user-centric tools—leveraging generative models, agentic workflows, and cloud-native services—that transform how teachers instruct, how schools operate, and how students learn.

Key Responsibilities

AI Strategy & Vision: Define the network-wide AI roadmap in close collaboration with executive leadership, educators, and product teams to turn cutting-edge AI capabilities into scalable tools.

Engineering Leadership: Build, mentor, and manage a high-performing team of AI software engineers and product-focused developers, fostering a culture of rapid prototyping, continuous learning, and software excellence.

Architecture & Delivery: Oversee the end-to-end design and integration of AI applications, intelligent agents, Retrieval-Augmented Generation (RAG) systems, and custom UI/UX touchpoints into our enterprise stack.

Enterprise Cloud Integration: Partner with Cloud Engineering to deploy secure, high-availability AI services across AWS and GCP environments using modern CI/CD practices.

Stakeholder Enablement: Act as a trusted advisor to school leaders and non-technical stakeholders, translating complex AI capabilities into practical use cases that drive real-world adoption.

Governance & Responsible AI: Establish enterprise guidelines for AI usage, data privacy (FERPA compliance), bias mitigation, model evaluation, and safety guardrails.

Qualifications

Leadership Experience: 7+ years in software engineering leadership, with a track record of hiring, mentoring, and leading high-performing engineering teams.

AI Application Delivery: 5+ years of experience delivering production-grade software applications, with demonstrable experience building and shipping AI/LLM-powered features at scale.

Modern AI Tech Stack: Proficiency with LLM orchestration frameworks (e.g., LangChain, LlamaIndex), AI APIs (OpenAI, Anthropic, Vertex AI, Bedrock), vector databases, and modern Python-based microservices.

Software Engineering Foundations: Strong foundation in API design, cloud architecture (AWS/GCP), system integration, and standard software engineering practices.

Product & User Focus: Proven ability to translate user needs into technical solutions with a strong focus on UX, user adoption, and business impact.

Mission Alignment: Passion for K-12 education and a commitment to Success Academy’s mission.

Compensation, Benefits & Perks

At Success Academy, we invest boldly in our Network team with a comprehensive package designed to support your health, financial future, and overall well-being:

Day-One Health & Wellness: Medical, dental, and vision coverage starting your first day (SA covers 82% of our core medical plan), plus a free One Medical membership and confidential mental health support via EAP/Talkspace.

Financial Security: 403(b) retirement plan with a 3% employer match, up to $2,400/year in employer HSA contributions, employer-paid life/disability insurance, and Public Service Loan Forgiveness (PSLF) eligibility.

Time to Recharge: Generous paid time off, paid holidays, and paid parental leave.

Perks & Stipends: A $50/month cellphone stipend ($600/year), pre-tax commuter benefits, backup family care, and performance-based earning incentives.

This is a hybrid position based in our NYC Financial District office, requiring on-site work Tuesday through Thursday and remote work on Monday and Friday.

Exact compensation may vary based on skills and experience.

Compensation Range

$280,000—$300,000 USD