Senior Program Manager, AI & Legal Technology

Okta•Chicago, IL

2d•Hybrid

About The Position

Okta is seeking a Sr. Program Manager, AI & Legal Technology to join our Legal Operations Team, reporting to the Director of Legal Systems and Technology. In this strategic role, you will be a visionary leader within the Legal Team, architecting the next generation of our technology roadmap with a primary focus on Artificial Intelligence (AI) and Machine Learning (ML) integration. You will drive world-class operational excellence by identifying and deploying AI-driven systems and data strategies that empower our legal team to achieve bold ambitions with increased velocity. You will lead the implementation of innovative technologies—such as LLM-powered assistants and advanced automation—while collaborating cross-functionally with Technology,Data, and Intelligence (TDI), Finance, Security, and Procurement to ensure a scalable, high-performing legal tech ecosystem.

Requirements

Bachelor’s Degree or equivalent with 5+ years of experience in Legal Operations or Technology Program Management.
Proven success leading AI tech implementations or workflow automation tools, with a deep understanding of LLM capabilities (e.g., Gemini, GPT, Copilot).
Deep familiarity with Conga preferred and workflow automation is required.
Ability to influence and engage stakeholders at all levels, translating complex AI and technical concepts into strategic legal outcomes.
Skilled in establishing a culture of continuous improvement through agile methodologies and metrics-based feedback mechanisms.
Experienced in working with Sr. Executives and global teams to assist in influencing organizational strategy.

Responsibilities

AI Roadmap Leadership: Lead the vision and execution of the Legal AI roadmap, partnering across Legal to identify and prioritize use cases and collaborating with the teams to bring these use cases to life.
Prompt Engineering & Optimization: Author, test, and maintain a centralized library of prompts for legal tasks such as contract summarization, litigation triage, and research.
AI Risk & Security Oversight: Partner with Security and Privacy teams to vet AI vendors for use on the Legal team , performing tests to mitigate risks like hallucinations and ensure IP protection.
Nascent Tech Assessment: Conduct ongoing assessments of existing and upcoming AI tools to identify enhancements that increase departmental productivity.
Portfolio Support: Own the strategy and support for the Legal tool portfolio, including CLM (Conga), workflow automation, eBilling, and AI-powered systems.
AI Implementation: Lead vendor selection, global rollout, and user acceptance testing (UAT) for AI-powered legal technologies and complex workflow automation platforms.
Workflow Design: Architect and implement AI-assisted workflows focused on reducing bottlenecks, including eliminating redundant queues and automating manual contract generation.
Data-Driven Decisions: Leverage advanced reporting and analytics to build AI based dashboards that track legal spend, AI adoption, and overall team performance.
Change Management & Training: Establish core documentation and training to foster AI literacy and ensure successful adoption of new technologies across the global team.
Strategic Collaboration: Act as the primary liaison between Legal, TDI, and corporate AI team to resolve complex technical issues and drive internal AI tool development.