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.

Duties and Responsibilities:

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.

Education and/or

Experience:

Required:

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.

Preferred:

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.

Other

Skills and Abilities:

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…