Remote Senior Program and Project Manager

Job Title: Senior Program and Project Manager Location: Pittsburgh, PA Preferred / Hybrid (Tuesday–Thursday Onsite) or 100% Remote for Non-Local Candidates Duration: 12 Months +/ Job Type: Contract-to-Hire Shift Schedule: Monday to Friday, Normal Business Hours Work Arrangement: Hybrid for Pittsburgh-area candidates; Fully Remote for non-local candidates About Sigma Systems Inc. (Staffing Agency) Sigma Systems Inc. is a trusted staffing partner delivering highly qualified professionals to clients across technology, healthcare, and government-regulated industries. We specialize in long-term contract and contract-to-hire opportunities, connecting experienced professionals with leading enterprise organizations. Position Overview: Senior Program and Project Manager Sigma Systems Inc. is currently seeking an experienced Senior Program and Project Manager to support one of our leading healthcare clients. This position is responsible for the successful delivery of large, complex, enterprise-level initiatives supporting strategic, operational, regulatory, and market-readiness objectives. The ideal candidate will have a strong background in project and program management , excellent executive communication skills, and the ability to lead large cross-functional initiatives involving both business and technology teams. This role requires a leader who can operate at the Program Manager level while remaining grounded in strong Project Management discipline , taking ownership of scope, schedule, budget, resources, risks, dependencies, governance, implementation, and overall business outcomes. Candidates must have strong soft skills and executive presence, with the ability to confidently present information, recommendations, risks, and project outcomes to high-level executives. Key Responsibilities: 1. Program & Project Delivery Leadership: Lead large, complex enterprise technology and business initiatives from planning through implementation. Manage projects involving multiple business, technology, and product areas, potentially spanning 30–60 different product areas . Serve as the single point of accountability for project and program outcomes. Ensure projects are delivered on time, within budget, and according to agreed business objectives. Coordinate multiple workstreams and cross-functional teams throughout the project lifecycle. 2. Strategic Planning & Execution: Develop and execute integrated delivery plans covering scope, schedule, resources, dependencies, milestones, and business objectives. Align technology and business workstreams to achieve committed outcomes. Establish priorities and drive execution in complex and ambiguous environments. Identify gaps and create clarity around objectives, ownership, timelines, and deliverables. 3. Executive & Stakeholder Engagement: Build strong partnerships with business, technology, product, operations, and other stakeholders. Present project status, risks, issues, recommendations, and outcomes to senior leadership and high-level executives . Communicate complex information clearly, concisely, and effectively to diverse audiences. Facilitate executive-level discussions and decision-making. Influence stakeholders and drive alignment without direct authority. 4. Risk, Issue & Dependency Management: Proactively identify and manage risks, issues, assumptions, and dependencies. Develop mitigation and contingency strategies to protect delivery commitments. Escalate critical issues appropriately and provide leadership with actionable recommendations. Resolve roadblocks and conflicts across multiple teams and workstreams. Maintain visibility into interdependencies that could impact project delivery. 5. Financial & Resource Management: Manage project budgets, forecasts, staffing plans, and resource allocation. Monitor project financial performance and identify potential budget risks. Partner with business and technology leaders to ensure appropriate resource allocation. Manage competing priorities and resources across multiple initiatives. 6. Governance & Decision Management: Ensure projects follow established project management, governance, and Delivery Excellence standards. Maintain appropriate project controls, documentation, reporting, and decision records. Drive timely decision-making and accountability across stakeholders. Ensure adherence to change management and organizational processes. 7. Business Readiness & Implementation: Incorporate business readiness activities throughout the project lifecycle. Lead operational readiness, implementation, transition, and adoption activities. Coordinate training and organizational readiness activities as needed. Ensure business teams are prepared for successful implementation and adoption. Drive projects beyond technical delivery to achieve the intended business outcomes. 8. Leadership & Team Management: Lead cross-functional teams and create accountability across business and technology organizations. Facilitate collaboration among teams that do not report directly to the Project Manager. Motivate teams, resolve conflicts, and remove barriers to execution. Lead through ambiguity and establish clarity, alignment, and accountability. 9. Continuous Improvement: Apply lessons learned and industry best practices to improve project and program delivery. Identify opportunities to improve governance, processes, and organizational effectiveness. Promote consistent project management practices across initiatives. Qualifications: Education: Bachelor's degree required. Experience: Minimum of 7 years of project management experience . Demonstrated experience successfully delivering large, complex projects on time and within budget . Experience managing multiple projects or workstreams concurrently. Experience leading cross-functional teams across business and technology organizations. Experience managing projects through the full project lifecycle. Demonstrated ability to operate at the Program Manager level while maintaining strong Project Management discipline . Project Management Skills: Strong understanding of project management principles, methodologies, and best practices. Hands-on experience with Agile, Waterfall, and/or Hybrid project delivery methodologies. Strong scope, schedule, budget, resource, risk, issue, and dependency management skills. Experience with project governance, controls, and change management. Strong strategic planning and execution capabilities. Executive & Communication Skills: Exceptional written and verbal communication skills. Strong executive presence and interpersonal skills. Ability to present complex information clearly and concisely to senior executives and leadership teams . Strong negotiation, influencing, facilitation, and stakeholder-management skills. Ability to build relationships and influence stakeholders without direct authority. Core Competencies: Strong business acumen. Strategic thinking and problem-solving abilities. Ability to lead through ambiguity and drive clarity. Strong organizational and time-management skills. Ability to prioritize competing demands. Strong decision-making and conflict-resolution skills. Results-oriented approach with a focus on accountability and business outcomes. Ability to lead large, complex, cross-functional initiatives. Preferred Qualifications: The following qualifications are preferred but not mandatory : Experience in the healthcare or health insurance industry . Previous experience with Highmark is a strong plus. Commercial health insurance product implementation experience. Government health insurance product implementation experience. Experience with Open Enrollment (OEP/AEP) readiness planning . Experience with Monday.com . Experience with Planview . Experience with Oracle ERP Resource and Financial modules . Experience leading enterprise-scale technology and business transformation initiatives. Ideal Candidate Profile The ideal candidate is a Senior Project Manager / Program Manager who has successfully led large enterprise initiatives involving multiple business and technology teams. The candidate should be able to: Own the initiative from strategy through implementation. Manage complex projects involving numerous product areas and stakeholders. Present confidently to executives and senior leadership. Manage budgets, resources, risks, issues, and dependencies. Influence stakeholders without direct authority. Lead teams through ambiguity and organizational complexity. Connect technology delivery with business readiness and measurable business outcomes. Operate strategically as a Program Manager while maintaining strong Project Management fundamentals. Healthcare/health insurance experience is highly desirable, but strong enterprise Program/Project Management experience may be considered in place of industry experience. Location & Work Arrangement Local Pittsburgh-area candidates are strongly preferred. Pittsburgh-area candidates: Hybrid work arrangement, with onsite presence generally required Tuesday, Wednesday, and Thursday based on business needs. Non-local candidates: Position may be 100% remote . Candidates should clearly communicate their current location and ability to support the required onsite schedule if local. Why Work with Sigma Systems Inc.? Opportunity to work with a leading enterprise healthcare organization. Long-term contract-to-hire opportunity. Competitive salary upon conversion. Remote flexibility for qualified non-local candidates. Opportunity to lead large, high-visibility enterprise initiatives. Exposure to senior executives and cross-functional business and technology teams. Potential for long-term career growth within a major enterprise environment. How to Apply If you are an experienced Senior Program Manager, Senior Project Manager, Enterprise Project Manager, or Technology Program Manager with a proven track record of delivering complex initiatives and communicating effectively with executive leadership, apply today with your updated resume. Candidates with healthcare/health insurance experience, executive presentation experience, enterprise technology delivery experience, and strong program-level leadership are especially encouraged to apply.