Sr. Director, Technology Program Portfolio Manager

Information Technology Chicago, Illinois


Company: Oak Street Health 

Title: Sr.Director, Technology Program Portfolio Manager

Location: Treehouse or Downers Grove

Oak Street Health is a rapidly growing public company of primary care centers for adults on Medicare in medically-underserved communities where there is little to no quality healthcare. Oak Street’s care is based on a unique model that is focused on value for its patients, not on volume of services. The company is accountable for its patients’ health, spending more than twice as long with its patients and taking on the risks and costs of their care. For more information, visit

For more information, visit


Role Description:

The Sr.Director Portfolio Manager is responsible for the oversight and administration of the program/project portfolio. This includes working with management and staff across the organization to assess, document, and budget potential projects; oversee project commencement and prioritization; perform project resource planning; continuous monitoring and reporting on project status; participate in the department’s change management process; and play an integral role in the annual capital budget process. The role will also involve oversight of the yearly capital budget process and working closely with the firm’s functional and administrative department heads as required. The Portfolio Manager will also work to develop and implement best practices, processes, and toolsets for effective portfolio/project management, and will help educate staff on best practices and effective project execution.


The Portfolio Manager works closely with the firm’s Project Management Office – meeting regularly with the manager of the PMO and assisting with governance of the firm's overall project portfolio. The Portfolio Manager will need to interact with firm administration and leadership to identify potential projects that best align with the strategic priorities of the firm. The Project Manager also works with the firm PMO on project risk and status reporting. The position involves working with all levels of IT and leadership and in gathering project metrics to ensure successful delivery of program initiatives.

Core Responsibilities:

  • Manage the project portfolio covering a wide range of cross departmental initiatives from intake to delivery in an Agile environment.

  • Work with the leadership team, department directors and project business sponsors to provide a comprehensive overview of capital and operational projects (overview includes the anticipated overall budget for each initiative in the portfolio).

  • Work collaboratively with the leadership team on project requests, processes and procedures through project completion.

  • Perform project scheduling, resource planning, leveling and management (forecast impacts on staffing where project scope may have changed) – as well as effective use of metrics, and reporting.

  • Manage all aspects of change and risk oversight.

  • Coordination of stakeholder and sponsor communications.

  • Track and report project statuses on a timely basis to IT leadership, stakeholders and sponsors.

  • Facilitate and oversee the establishment of a “Portfolio Review Committee” to manage the processes of reviewing new proposals and introducing new assets into the portfolio.

  • Coordinate with the Architecture team to assist in facilitating the new vendor technical review process and cloud vendor review procedures.

  • Work with all levels of firm leadership to ensure project initiatives are managed and maintained; develop executive level presentations of the portfolio and project budget.

  • Manage the annual capital budget process through inception to final approval by senior leadership.

  • Develop an overall understanding of each initiative in the portfolio to understand the potential customer impact and service requirements generated by each initiative in the portfolio.

  • Provide quality assurance ensuring that initiatives are being well managed and adhering to appropriate standards and good practice.

  • Recalibrate the portfolio as necessary when the demands of the business dictate a change in delivery or scope of work.

What are we looking for?

  • Excellent interpersonal and communications skills (both oral and written) with the ability to clearly communicate complex messages to a variety of audiences.

  • Strong decision making skills. Able to make decisions quickly and efficiently.

  • Demonstrated competency in developing and managing complex project plans, timelines, budgets, and critical paths.

  • Thorough knowledge and related work experience of the project management process, theory and lifecycle, including Waterfall and Agile methodology, as well as Project Delivery Framework and SDLC.

  • Detail-oriented with proven ability to adapt to a dynamic environment and oversee multiple projects, manage schedules, resource allocation/planning and maximize work efforts across all teams.

  • Possess excellent prioritization, resource planning and management skills as well as proven ability in the identification, assessment and contingency planning and managing for risk factors.

  • Proven competency to effectively interact at all levels across the organization, working to build and maintain successful relationships across all departments.

  • Proven competency in business analysis, requirements definition, and business case production.

  • Skilled at creating and delivering executive level presentations.

  • Proven consultative, conflict resolution, negotiation and facilitation skills to gain consensus and ensure delivery of initiatives.

  • Demonstrated flexibility and be able to work in a time-sensitive environment and meet strict deadlines with sudden and unpredictable changes that may occur.

  • Ability to improve current processes and procedures; present opportunities for change and help implement them for the benefit of the firm.

  • Possess a thorough understanding of information technology and its application to business issues; understands the use of information technology in a strategic context as a means to an end; is conversant with current technologies and trends relevant to the firm.

  • Self-starter with a strong work ethic, who sets high standards for self and others and demonstrates enthusiasm for the mission of the team.



  • Minimum of 10 years of industry experience in large scale implementations preferably in the professional services sector, with an emphasis on enterprise information systems across multiple functions.

  • Minimum of 10 years of experience in portfolio, program and/or project management with a successful project management track record in full life cycle information technology implementation projects, with proven record of execution to time and budget.

  • Knowledge and understanding of standard project management tools (for example, MS Azure DevOps, MS Project, JIRA, Product Board, Asana).

  • Knowledge and understanding of Large Scale Scrum.

  • Ability to work independently with minimum supervision.

  • Healthcare related knowledge is preferred, not required.

  • PMP preferred, not required.

  • CSM (Certified Scrum Master) preferred, not required

  • B.S., B.A. or equivalent.

  • US work authorization

  • Someone who embodies being “Oaky”

What does being “Oaky” look like?

  • Radiating positive energy

  • Assuming good intentions

  • Creating an unmatched patient experience

  • Driving clinical excellence

  • Taking ownership and delivering results

  • Being scrappy


Why Oak Street?

Oak Street Health offers our coworkers the opportunity to be at the forefront of a revolution in healthcare, as well as:

  • Collaborative and energetic culture

  • Fast-paced and innovative environment

  • Competitive benefits including paid vacation and sick time, generous 401K match with immediate vesting, and health benefits

Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply to