Head of Data & AI Program Management

Sidley Austin LLP; Chicago (IL); Hybrid; USD 232,000 - 330,000; Full time

Benefits offered by this job

Bonus eligibility

Comprehensive benefits

Job summary

Sidley Austin LLP in Chicago seeks a seasoned Program Management Director to anchor the Data & AI organization. You will lead a cross-functional team of ~100 professionals, standardize Agile practices, and ensure delivery across initiatives with Jira, Confluence, and Aha!.

You will partner with leadership to track OKRs and KPIs, govern with cadence reviews, and mentor a growing PM team while driving operational excellence and strategic impact.

Qualifications

• Minimum 10 years of program or project management experience, including at least 5 years in a leadership capacity.
• Experience managing large cross-functional programs (100+ people) with measurable accountability outcomes.
• Deep proficiency with Jira, Confluence, and roadmapping tools.
• Proven expertise implementing and scaling agile delivery 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.

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.

Skills

Program management

Leadership

Executive communication

Stakeholder management

Education

Bachelor's degree in Business, Engineering, Computer Science, or a related field

Master's degree in Business Administration, Engineering, or a related field

Tools

Jira

Confluence

Aha!

Roadmapping tools

Job description

Sidley Austin LLP in Chicago seeks a seasoned Program Management Director to anchor the Data & AI organization. You will lead a cross-functional team of ~100 professionals, standardize Agile practices, and ensure delivery across initiatives with Jira, Confluence, and Aha!.

You will partner with leadership to track OKRs and KPIs, govern with cadence reviews, and mentor a growing PM team while driving operational excellence and strategic impact.