Senior Technical Program Manager, AI

brightwheel

3d•$154,000 - $237,000

About The Position

Brightwheel is seeking an AI-native Senior Technical Program Manager to drive its most complex, technically challenging, and multi-stakeholder initiatives. This role requires a blend of deep systems-level engineering judgment, strong product sense, and exceptional execution skills. The ideal candidate will act as the technical glue in ambiguous spaces, transforming company-wide priorities into high-velocity delivery across multiple engineering pods, product lines, and operations teams. They will lead by example in modern, automated execution, ensuring AI-driven capabilities are safe, scalable, and delivered with incredible velocity. The role focuses on scaling Brightwheel's value and impact by orders of magnitude, ruthlessly unblocking technical dependencies and managing systemic risks. This is a hands-on, practitioner-leader role that utilizes AI assistants, agents, and modern tooling for automation, tracking, scripting, and prototyping.

Requirements

A strong computer science foundation: You have a 4-year computer science degree or equivalent depth in core CS topics, giving you the technical grounding to reason well across distributed systems, machine learning abstractions, and data architecture.
A record of orchestrating complex systems at scale: You have a proven track record of landing highly technical, multi-team programs from inception to production deployment. You understand what it takes to make deeply integrated products succeed in live production environments.
Applied AI familiarity in production: You have driven programs involving AI, LLM orchestration, or automated data pipelines. You understand the nuances of non-deterministic software, including evaluation, prompt engineering, latency bottlenecks, and safety boundaries.
Influence without authority: You have extensive experience driving alignment across senior engineers, product directors, and executive stakeholders without having direct reporting lines over them.

Nice To Haves

Product taste and technical intuition: You operate without needing a product manager crutch. You use your deep technical knowledge to bridge the gap between architectural constraints and consumer value, ensuring we build the right things the right way.
A "T-Shaped" builder mindset: You are deeply expert in program execution and system architecture, but capable of diving just-in-time into data engineering, cloud infrastructure, or frontend flows. You use AI to multiply your learning speed, allowing you to confidently review code or write scripts to validate integration paths.
Fearless handling of ambiguity: You run toward the company's messiest, least-defined technical friction points. You create structure, define clear milestones, and build high-fidelity alignment where none existed.
Hands-on fluency with AI-native development: You don't just write documentation; you use AI coding tools (Claude Code, Cursor, v0) to automate your own technical tracking, build internal tooling dashboards, or construct technical proof-of-concepts to unblock engineering discussions.

Responsibilities

Drive high-stakes, multi-stakeholder technical programs that embed AI capabilities across our entire product surface area—ensuring tight synchronization between data, platform, and frontend product teams.
Manage the complex execution dependencies of building software that recommends next steps, completes routine work, and automates meaningful parts of our customers’ operations.
Partner with engineering leadership to design and operate an AI hybrid workforce, establishing the necessary guardrails, evaluation frameworks, governance, and observability required for autonomous agents.
Streamline internal engineering velocity by implementing AI-powered tooling, automated testing pipelines, and agentic workflows that catch issues early and minimize operational overhead.
Apply an AI-native programmatic approach to optimizing internal functions like customer support and onboarding, ensuring cross-functional alignment as we scale.
Facilitate critical technical trade-offs, driving consensus on build-versus-buy decisions, architectural patterns, and platform leverage without losing momentum.