Program Management Director

The Program Management Director will be the operational backbone of Sidley's Data & AI organization—a fast-moving, cross-functional team comprising AI Engineering, Data Engineering, UX Design, Product Management, and Data Governance. This leader will instill rigor, accountability, and scalable program management practices across a team of approximately 100 professionals.

Reporting to the Product Management Senior Director, this role will inherit and grow a team of two Program Managers and will serve the entire Data & AI organization. The ideal candidate is a meticulous, highly organized operator who thrives in complexity, leads with structure, and is not afraid to hold people accountable—at every level—to milestones, deadlines, KPIs, and OKRs.

• Lead the end-to-end program management framework for the Data & AI organization, ensuring delivery, visibility, and accountability across all initiatives.
• Establish and standardize Agile program management practices, including Jira workflows, sprint planning, backlog management, and reporting.
• Develop executive dashboards to track portfolio health, milestones, resource allocation, risks, and dependencies.
• Partner with Data & AI leadership to define, track, and report on organizational OKRs, KPIs, and strategic priorities.
• Drive operational rigor through structured governance, including weekly, monthly, and quarterly program reviews.
• Proactively identify risks, remove blockers, and implement corrective actions to keep programs on track.
• Lead, mentor, and grow a team of Program Managers while fostering a culture of accountability, continuous improvement, and operational excellence.
• Collaborate with Engineering, Product, UX, Data Governance, and IT teams to manage cross-functional dependencies and deliver strategic initiatives.
• Serve as a trusted advisor to senior leadership on execution planning, organizational capacity, and operational risk.
• Drive adoption and optimization of Jira, Aha!, Confluence, and related collaboration tools as enterprise systems of record.
• Continuously improve program management processes, governance, and tooling to increase organizational efficiency, scalability, and predictable delivery.

• Bachelor's degree in Business, Engineering, Computer Science, or a related field.
• Minimum of 10 years of program or project management experience, including at least 5 years in a senior or leadership capacity at a high-performing organization.
• Demonstrated experience managing large, cross-functional programs (100+ person organizations or equivalent scope) with measurable accountability outcomes.
• Deep proficiency with Jira, Confluence, and road mapping tools—including workflow configuration, reporting, and driving org-wide adoption of standards.
• Proven expertise implementing and scaling agile delivery practices across multi-disciplinary technology teams.
• Track record of building and maintaining OKR/KPI frameworks and driving organizational accountability to them.
• Experience directly managing and developing program management professionals.
• Strong executive presence with the communication and influencing skills to engage senior leadership and firm stakeholders with confidence and clarity.
• Comfortable making the difficult call: holding teams accountable, escalating blockers, and driving decisions when momentum stalls.
• Demonstrated ability to operate effectively in a matrixed, fast-paced environment with competing priorities and evolving requirements.

• Master's degree in Business Administration, Engineering, or a related field.
• PMP, PgMP, SAFe, or equivalent program management certification.
• Experience in a law firm, professional services, or similarly complex enterprise environment.
• Familiarity with AI, data engineering, or data governance domains and the unique delivery challenges they present.
• Experience managing geographically dispersed teams across multiple time zones.

The following will also be required of the successful candidate:

• Strong organizational skills
• Strong attention to detail
• Good judgment
• Strong interpersonal communication skills
• Strong analytical and problem-solving…