Strategic Planning Specialist

Job Title: Strategic Planning Specialist
Location: Remote
Pay Rate: W2 only (no c2c)
Position Type: Multiyear Contract

Candidates must live in the United States. This role requires someone with 7-10 years of experience working in a PMO, Program Management, Strategic Planning, Agile Program Delivery, or Governance Office, and is highly proficient with Azure DevOps (ADO).

We are not looking for a Scrum Master or Agile Coach or technical delivery focused specialist. We are looking for a Strategic Planning/PMO professional who helps organizations plan, align, communicate, and track priorities across multiple teams. We are looking for candidates with direct experience with strategic planning, PMO/governance functions, portfolio management, executive reporting, organizational change, planning processes, and cross functional coordination/alignment. We are looking for someone who can help mature and operate the planning framework, facilitate alignment across teams, maintain ADO dashboards/reporting, develop communications and documentation, and drive continuous improvement.


The Strategic Planning Specialist supports the planning, governance, and execution of strategic initiatives within a Security Governance & Risk (SGR) organization. The role focuses on managing planning processes, maintaining Azure DevOps (ADO) planning tools, coordinating quarterly and annual planning cycles, tracking deliverables and milestones, improving governance processes, supporting stakeholder engagement, and driving adoption of planning frameworks. The position combines program management, Agile delivery, process improvement, change management, and stakeholder coordination to help leadership execute strategic priorities effectively.

Strategic Planning Specialist
We are seeking an experienced consultant to support the continued implementation and maturation of the Security Governance & Risk (SGR) Strategic Planning Framework. The ideal candidate is a seasoned program management professional with strong Agile delivery experience who can quickly integrate into the team, provide operational support for annual and quarterly planning cycles, and help drive process adoption, consistency, and continuous improvement across multiple teams.

Key Responsibilities

• Administer and maintain Azure DevOps (ADO) backlogs, dashboards, delivery plans, queries, and Wiki content supporting annual and quarterly planning activities.
• Coordinate planning cycle execution, including readiness activities, deliverable tracking, status reporting, and milestone management.
• Develop, maintain, and communicate planning processes, procedures, job aids, training materials, and supporting documentation.
• Serve as a primary point of contact for teams seeking guidance on planning processes, quarterly commitments, reporting expectations, and progress tracking.
• Identify opportunities to improve planning, governance, and reporting processes; develop recommendations and assist with implementation of approved enhancements.
• Facilitate stakeholder engagement activities, including workshops, communications, change management, and adoption support.
• Monitor planning deliverables, risks, dependencies, and action items to help ensure timely execution and visibility for leadership.

• 5+ years of experience in program management, strategic planning, PMO, Agile delivery, or related disciplines.
• Advanced working knowledge of Azure DevOps (ADO), including backlog management, queries, dashboards, reporting, and Wiki administration.
• Strong facilitation, communication, stakeholder management, and organizational skills.
• Experience applying change management practices, including stakeholder engagement, communications planning, training development, and adoption strategies.
• Ability to work independently with minimal direction while effectively collaborating across teams with varied levels of planning maturity.

• Experience within information security, risk management, governance, compliance, or regulatory environments.
• Experience supporting enterprise planning, portfolio management, or value delivery/workstream definition initiatives.
  
  
  System One, and its subsidiaries including Joulé and Mountain Ltd., are leaders in delivering outsourced services and workforce solutions across North America. We help clients get work done more efficiently and economically, without compromising quality. System One not only serves as a valued partner for our clients, but we offer eligible employees health and welfare benefits coverage options including medical, dental, vision, spending accounts, life insurance, voluntary plans, as well as participation in a 401(k) plan.

System One is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, age, national origin, disability, family care or medical leave status, genetic information, veteran status, marital status, or any other characteristic protected by applicable federal, state, or local law.

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