Digital Program Management Sr Manager

Freeman•Chicago, IL

13h•Hybrid

About The Position

The Freeman Company is seeking a Digital Program Management Senior Manager to lead planning, governance, and delivery across its Digital Commerce program portfolio. Reporting to the VP, Digital Program Management, this player-coach will run the Commerce delivery practice day to day, including its operating model, governance, tooling, reporting, and risk management, while personally leading several high-priority, revenue-driving programs. The role directs contract program resources and represents the VP with senior leaders across Product, Merchandising, Strategic Planning & Analysis, and Technology. It will help establish a delivery model in which experienced teams manage their work with effective tools and AI support rather than excessive oversight. The Senior Manager will build and improve the Commerce operating model and portfolio governance, oversee delivery health across more than a dozen programs, and personally lead two to four complex, cross-functional programs. The role owns program management standards and reporting, including Adobe Workfront configuration standards and system-generated portfolio reporting, and leads adoption of AI and automation to reduce manual program-management effort. It also builds the practice’s foundation for future growth through role expectations, onboarding, playbooks, and development paths. The position requires travel up to 25%. The role offers a salary range of $130,000–$160,000 based on experience and eligibility for an annual bonus of up to 7.5% of base salary. The Freeman Company describes the position as hybrid through the #LI-Hybrid tag.

Requirements

13+ years of progressive program and project management experience leading digital, technology, or transformation programs at enterprise scale.
At least 3 years leading people or a program management practice.
Demonstrated success designing or improving governance, intake, and portfolio management processes.
Experience personally delivering complex, multi-workstream initiatives end to end.
Ability to lead executive steering committees, coach contractors, and contribute directly to delivery plans.
Strong executive presence and ability to influence senior leaders who do not report to the role-holder, including delivering difficult messages clearly and confidently.
Ability to establish useful structure without unnecessary bureaucracy and to determine when processes help or hinder.
Systems-thinking ability to design an operating model and drive its adoption.
Genuine curiosity about AI and emerging tools, with experimentation in how they can change program management.
Ability to build trust across functions and levels and make complex work manageable for teams.
Fluency across program methodologies, with a bias toward action and outcomes over process for its own sake.

Nice To Haves

Direct experience in a lead role within Scaled Agile.
Experience operating in a large-scale enterprise environment.
Experience with e-commerce or customer-facing digital platforms, such as Salesforce Commerce Cloud.
Experience with enterprise work-management tools, such as Adobe Workfront.

Responsibilities

Lead, coach, and direct contract program and project managers; set expectations, allocate resources across programs, and hold them accountable for quality and outcomes.
Partner with the VP, Digital Program Management to translate Commerce strategy and priorities into a delivery roadmap, operating rhythm, and quarterly plans.
Represent the VP in portfolio reviews, steering committees, and cross-functional leadership forums.
Mentor the Sr. Digital Program Manager and contributors across Commerce and partner teams.
Build foundations for a growing team, including role expectations, onboarding, playbooks, and development paths.
Manage contractor sourcing, statements of work, budgets, and time tracking with Finance and Procurement, ensuring CapEx compliance.
Design, implement, and improve the Commerce operating model, including intake, prioritization, program tiering, stage gates, RACI decision rights, and planning cadence.
Run portfolio reviews with Commerce leadership and steering committees for critical programs; tailor governance to each program’s needs.
Own RAID standards and the portfolio-level risk view, ensuring significant risks have owners, mitigation plans, and timely escalation.
Define and track delivery KPIs reflecting portfolio health, predictability, and business value.
Personally lead two to four complex, cross-functional, revenue-driving programs end to end, owning integrated plans, dependencies, vendors, and executive communications.
Oversee delivery health across a portfolio of more than a dozen programs and course-correct work that is off track.
Define success metrics and value baselines for priority programs and report value realized as well as milestones.
Apply waterfall, agile, scrum, kanban, or hybrid approaches according to each initiative’s needs.
Own program-management tooling, including Adobe Workfront configuration standards, templates, data quality, and roadmap; partner with IT on administration and integrations.
Own portfolio reporting, including weekly executive status, leadership presentations, and dashboards generated from the system of record.
Identify, pilot, and scale AI assistants, agents, and automation for status reporting, meeting follow-up, RAID management, and intake.
Provide peer teams with self-service templates, playbooks, training, and AI assistants, coaching without micromanaging.
Travel up to 25%.