Remote Software Delivery Manager Jobs in Madison, WI

The Wisconsin Foundation and Alumni Association (WFAA)*, the private fundraising and alumni relations organization for UW-Madison, is seeking an experienced Principal IT Project Manager to join our Project Portfolio Planning and Management Office (P3MO). This senior-level role combines hands-on delivery of complex IT projects with organizational responsibility for defining and advancing the enterprise's project management methodology and standards. Reporting to the P3MO Manager, the Principal IT Project Manager serves as a functional authority on how projects are managed across the IT organization, setting PM standards, driving continuous improvement, and mentoring project managers across the team. PMP certification and experience building or maturing a PM practice are strongly preferred.

The Principal IT Project Manager contributes deep IT project delivery experience and project management methodology expertise to the Project Portfolio Planning and Management Office. This role provides functional leadership for how project management is practiced across the organization by owning the PMO methodology framework, setting standards, and continuously improving how projects are initiated, executed, and closed. In close partnership with the PMO Manager, the Principal IT Project Manager helps ensure portfolio projects are supported by a disciplined, consistent delivery practice.

If you are passionate about elevating the discipline of project management and driving delivery excellence through structured, consistent practices and emerging AI-assisted tools, please apply!

Please note: This position can be hired as hybrid or 100% remote for the right experience level. Remote candidates must reside in the following states to be considered: Arizona, Colorado, Illinois, Iowa, Kentucky, Minnesota, Nebraska, New Mexico, New York, Texas, and Wisconsin. 

PMO Standards, Methodology & Governance 

• Methodology Ownership: Define, own, and maintain the organization's project management methodology, selecting and tailoring frameworks (Agile, Waterfall, Hybrid, Kanban) to organizational context and project type.
• Governance & Intake: Establish and enforce PMO governance processes including project intake, stage-gate reviews, and escalation paths.
• Standards Library: Develop, publish, and maintain a comprehensive library of PM standards, templates, playbooks, and toolkits (charters, RAID logs, status reports, lessons learned, etc.).
• Project Classification: Define and operationalize project classification tiers (e.g., small/medium/large/transformational) with associated methodology and oversight requirements.
• PMO Maturity: Lead periodic PMO maturity assessments and develop roadmaps to advance organizational project management capability.
• Metrics & KPIs: Establish metrics and KPIs for project performance and PMO effectiveness; report findings to senior leadership.
• Mentoring: Serve as a mentor and go-to resource for project managers at all levels, providing guidance on methodology application, PM standards, and stakeholder management.
• Competency Frameworks: Develop PM competency frameworks and reference materials that support consistent standards adoption across the team.
• Industry Currency: Stay current with industry trends (PMI, Agile Alliance, Gartner) and proactively recommend methodology updates.

IT Project Management 

• Project Delivery: Manage a portfolio of complex, high-visibility IT projects from initiation through closure, ensuring delivery on time, within scope, and within budget.
• Stakeholder Alignment: Collaborate with senior leadership and stakeholders to define project objectives, gather requirements, and align projects to strategic business goals.
• Team Leadership: Lead cross-functional project teams through design, development, testing, and implementation phases.
• Risk & Change Management: Identify, assess, and actively manage risks, issues, dependencies, and change requests across all assigned projects.
• Documentation & Communication: Maintain comprehensive project documentation and deliver clear, concise status communications to stakeholders at all levels.
• Role Flexibility: Flex into Product Owner, Scrum Master, or Business Analyst roles as project needs require.

PMO Tools, Processes & Continuous Improvement 

• Tooling Strategy: Own the selection, configuration, and adoption strategy for PMO tooling (Jira, Workfront, MS Project, Power BI dashboards, etc.).
• Reporting Frameworks: Develop standardized reporting frameworks and portfolio dashboards for executive and operational audiences.
• AI & Automation: Actively identify opportunities to apply AI tools and AI-assisted PMO tooling capabilities to automate the production and distribution of PM artifacts, reduce administrative burden, and enhance project delivery through intelligent scheduling, risk flagging, resource forecasting, and stakeholder communication - incorporating proven approaches into PMO standards.
• Lessons Learned: Lead lessons-learned programs and translate insights into actionable process improvements embedded in PMO standards.
• Continuous Improvement Culture: Champion a culture of continuous improvement, data-driven decision-making, and delivery excellence across the project management community.

Stakeholder Engagement & Executive Partnership

• Relationship Building: Build and sustain trusted relationships with IT leadership, business unit leaders, and executive sponsors.
• Advisory Role: Serve as a key advisor to leadership on project delivery risks, resource capacity, and methodology effectiveness.
• Communication: Communicate complex project and portfolio information clearly to both technical and non-technical audiences.

Required Qualifications:

• Bachelor's degree in Information Technology, Project Management, Business Administration, or equivalent experience.
• 10 + years of progressive IT project management experience, with at least 3 + years in a lead, principal, or PMO-level capacity.
• Demonstrated experience building or maturing a PMO or PM practice, including methodology design and standards implementation.
• Proven track record delivering complex, enterprise-scale IT projects with measurable business impact.
• Expert-level command of multiple project management methodologies: Agile, Scrum, Kanban, SAFe, Waterfall, and Hybrid approaches.
• Proficiency in PMO tooling including Jira, Workfront, MS Project, Microsoft Teams, SharePoint, and portfolio/reporting dashboards.
• Strong understanding of SDLC, IT infrastructure, and enterprise systems (CRM, ERP, Financial Reporting platforms preferred).
• Experience developing PM standards, templates, playbooks, and governance frameworks.
• Exceptional leadership, influence, and facilitation skills; able to drive alignment across diverse, cross-functional stakeholders without direct authority.
• Strong coaching and mentoring capabilities with a focus on elevating peers' application of PM methodology and standards.
• Excellent written and verbal communication skills, including executive-level presentation and reporting.
• High analytical aptitude; able to synthesize data and translate insights into strategic recommendations. Comfortable managing ambiguity, competing priorities, and organizational change.

Other Qualifications:

• Preferred Certifications:
  • Project Management: PMP (Project Management Professional), PRINCE2 Practitioner, PMI-PBA (Business Analysis)
  • Agile & Delivery: CSM / A-CSM (Scrum Master), PMI-ACP (Agile Certified Practitioner), SAFe Program Consultant (SPC)