Jobs · Business Development

AI Implementation Technical Program Manager

Cypress HCM · San Francisco, CA · 4 days ago
RemoteRemoteBusiness Development$112.56–$127.59/hrContract
Description CS Platform & Experience is responsible for defining the ideal support journey for guests and hosts, and developing the customer-facing and internal Community Support products and platforms that deliver world-class support. We partner across to integrate support into every product and service, and we are executing on an ambitious AI-native roadmap toward 10-star customer service. A foundational piece of that roadmap is the AI Skills Repository — a governed library of AI-powered skills built on Claude that automate, accelerate, and standardize workflows across the team. This role owns that repository end to end.The RoleWe are looking for an AI Implementation Technical Program Manager to build and steward the CS AI Tools Repository. This is a new, high-impact role at the intersection of AI product operations, knowledge management, and quality assurance. You will partner with product managers, engineers, operations leads, and frontline teams to turn institutional knowledge into reusable, verified, production-grade AI tools and keep them accurate, current, and effective as our products and processes evolve.You will own the full skills lifecycle: creation, verification, maintenance, and quality management. You will present creative ideas and prototypes of new skills to target audiences for feedback and implementation. You will define the standards and governance model for the repository, run evaluation frameworks to ensure AI tool quality, and serve as the authoritative voice on what "good" looks like for AI-assisted workflows in Community Support. Duties Partner with product managers, operations leads, and subject-matter experts across CS to identify high-value workflows suitable for AI tool development.Coordinate and conduct the development, testing, and implementation of AI skills + tools for internal teams ensuring a high standard of output from each tool.Define and steward the AI tools submission lifecycle including standardised templates, acceptance criteria, and governance across the end-to-end workflowDesign and operate a structured AI tool evaluation framework by defining test cases and pass/fail standards before any tool enters the repository.Own the ongoing health of the repository: monitor for use cases that become stale, inaccurate, or redundant as products, CS policies, or operational workflows change.Maintain a version history and changelog for every AI tool, enabling rollback and audit.Establish clear deprecation criteria and processes by retiring tools that no longer deliver value while communicating changes to affected teams.Define and own the CS AI tooling governance model: naming conventions, metadata standards, access controls, review cadences, and ownership assignment.Create and maintain a skills catalogue that makes the repository discoverable and usable for all CS team members including clear documentation of purpose, inputs/outputs, limitations, and known edge cases for every skill.Run regular repository audits, producing health reports that track coverage, quality scores, adoption trends, and outstanding gaps for leadership.Champion responsible AI practices, ensuring skills include appropriate guardrails, escalation paths, and human-in-the-loop checkpoints where required.Collaborate with the Chief of Staff to run team wide training sessions, produce newsletters and other communications ensuring alignment with the broader organization. Requirements 7+ years of experience in technical program management with a proven track record of success.Demonstrable experience working with AI tools, including prompt engineering, LLM-based product development, or AI workflow automation, with a strong instinct for where AI adds genuine value vs. where it introduces risk.Exceptional written communication: the ability to translate complex operational workflows into clear, precise, structured documentation that non-technical readers can act on.Experience designing and running quality or evaluation frameworks — you have a track record of defining what "good" looks like and holding work to that standard.Strong program management instincts: you can manage a portfolio of work across multiple stakeholders, balance competing priorities, and deliver reliably.A collaborative, ambitious, low-ego working style. This role requires influence without authority across product, engineering, operations, and analytics teams.Hands-on, working knowledge of software product development life-cycle and methodologies. Specific experience with Agile is preferred.PreferredExperience in a customer support, trust, or operations organization at a technology company.Understanding of data quality principles and experience working with analytics or data science teams to instrument impact metrics. Compensation $112.56 – 127.59/hr W—2 Req ID 37643599

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