PMO Strategic Projects Lead

Role Description

The PMO Strategic Projects Lead role leads and rolls out the end-to-end orchestration of strategic technology initiatives across our digital ecosystem — our learning management systems (LMS), web and content platforms (Drupal), headless commerce (Medusa), and product information / digital experience management (Pimcore) — along with the integrations and migrations that connect them. This is a hybrid role: part portfolio governance leader, part technically fluent program manager, and part change agent who brings stakeholders together and keeps delivery moving.

The role requires a rare blend of portfolio management expertise, hands-on Agile delivery discipline, applied technical fluency, and AI literacy, paired with the soft skills needed to influence without direct authority.

Key Responsibilities

• Portfolio Governance & Prioritization
  • Own the project intake, prioritization, and approval process, ensuring every initiative maps clearly to strategic objectives and measurable business value.
  • Own structured prioritization frameworks such as RICE (Reach, Impact, Confidence, Effort) and weighted/value-vs-effort scoring to rank competing demands objectively and defensibly.
  • Facilitate portfolio visibility on review boards, steering committees, and quarterly planning ceremonies, framing trade-offs and driving clear go / no-go / re-prioritize decisions.
  • Develop and maintain portfolio dashboards to track delivery health (change requests, MVP, scope, DoD, etc.), risk, cross-platform dependencies, capacity, and benefit realization to provide company visibility.
  • Enforce PMO standards — project charters, stage-gates, RAID logs, definition-of-done, and consistent status reporting — while keeping governance lightweight and value-adding rather than bureaucratic.
  • Partner with resource managers to align capacity and demand management across the portfolio.
• Agile Delivery & Scaled Frameworks
  • Drive delivery using Agile methodologies and scaled frameworks — SAFe (Scaled Agile Framework) and/or LeSS (Large-Scale Scrum) — coordinating across multiple teams, programs, and Agile Release Trains or iterative releases.
  • Support Lean Portfolio Management practices: align strategic themes to epics, manage portfolio Kanban / intake flow, and enable agile, incremental funding rather than fixed annual budgets.
  • Coordinate cross-team planning, dependency mapping, and synchronization so initiatives spanning LMS, Credit Reporting, Drupal, Medusa, Pimcore, etc., stay aligned.
  • Remove cross-program impediments, manage risks and dependencies proactively, and protect delivery cadence and flow.
  • Champion continuous improvement through retrospectives, flow metrics, and data-informed adjustments to ways of working.
• Technology Programs: Platforms, Integrations & Migrations
  • Collaborate on strategic technology integrations across the digital stack with the IT/Architecture teams: LMS platforms; Drupal (web/content management); Medusa (headless / composable commerce); and Pimcore (PIM / MDM / DAM / DXP) and any other platforms within our PMO portfolio.
  • Have basic understanding of systems integration and data-migration initiatives — connecting platforms through REST / GraphQL APIs, SSO, SCORM/AICC and other LMS standards, and iPaaS / middleware with rigorous planning for data quality, cutover, and rollback.
  • Translate between business stakeholders and engineering / architecture teams, ensuring requirements, sequencing, and technical trade-offs are clearly understood on both sides.
  • Maintain a program-level view of architecture dependencies, technical risk, and non-functional requirements (security, performance, scalability, regulatory compliance).
• AI Enablement in Portfolio & Delivery
  • Apply AI across the portfolio lifecycle: use generative AI for status synthesis, document and plan drafting, and meeting summarization; predictive analytics for forecasting delays, resource constraints; and emerging agentic capabilities for proactive risk surfacing.
  • Strengthen the data foundation (data quality, governance, and structure) that makes AI-assisted portfolio decisioning reliable and trustworthy.
  • Evaluate and responsibly adopt AI features within the toolchain (e.g., Atlassian Intelligence, Power BI Copilot, platform-native AI such as Pimcore’s automation/Copilot capabilities), establishing sensible guardrails for governance and oversight.
  • Support AI-related delivery initiatives across the platforms (e.g., personalization, content/data enrichment, intelligent search), partnering with product and engineering on scope and value.
• Tooling, Reporting & Insight
  • Run the portfolio in the Atlassian suite — Jira Cloud (intake, epics/initiatives, roadmaps, Advanced Roadmaps/Plans, Agile boards) and Confluence (governance documentation, decision logs, knowledge management).
  • Build executive-grade reporting and dashboards in Power BI, Jira or platforms such as Big Picture (and Excel), turning portfolio and delivery data into clear, actionable insight for leadership to visualize.
  • Define and track the metrics that matter — delivery predictability, flow/throughput, value realized, ROI, and risk exposure — and tell the story behind the numbers.
• Stakeholder, Leadership & Cross-Functional Influence
  • Act as the bridge between executives, functional leaders, product, engineering, and delivery teams — translating strategy into execution and execution status back into strategic insight.
  • Accountable for ensuring that all discussions result in clear decisions, defined ownership, actionable next steps, agreed scope boundaries, documented trade-offs, and transparent follow-through.
  • Demonstrates the ability to communicate with clarity, professionalism, and appropriate candor; facilitate alignment across diverse stakeholders; and accurately represent differing viewpoints while maintaining objectivity and organizational priorities.
  • Facilitate difficult prioritization and trade-off conversations with executive presence, building alignment among stakeholders with competing interests by providing clear recommendations, impact assessments, trade-off analyses to maintain alignment with portfolio objectives, timelines, budgets, and organizational priorities.
  • Provide coaching and support to project managers and workstream leads, and drive a culture of accountability, transparency, and continuous improvement across the PMO.
  • Provide resource allocation recommendations on capacity & projects’ needs (PMs, BSAs, etc.) based on projects’ plans, delivery and forecasted timelines.
  • Lead portfolio-level decision and escalation management paths, ensuring strategic, operational, and delivery risks are identified early, routed through the appropriate governance channels, and resolved in a timely manner.

Qualifications

• Bachelor’s degree in Business, Finance, IT, Computer Science, or a related field required; MBA preferred.
• PMP, PgMP, or PfMP required.
• Agile / scaling certifications strongly preferred (e.g., CSM/PSM, SAFe — SA / SPC / RTE, or Certified LeSS Practitioner).
• Change-management certification (e.g., PROSCI) a plus.
• AI / data-related credentials or demonstrable applied experience a plus.

Requirements

• 4-6+ years in program and portfolio management, including 2–3+ years leading enterprise transformation or technology-platform programs.
• Demonstrated success standing up or operating PMOs and managing portfolios in dynamic, multi-project environments.
• Hands-on delivery experience with web/content, commerce, PIM/DXP, or LMS platforms — such as Drupal, Medusa (or comparable headless/composable commerce), Pimcore (or comparable PIM/MDM/DXP), and learning management systems.
• Proven experience in IT systems integrations and data migrations (APIs, SSO, ERP/CRM, content or catalog migrations); ERP / HR / Finance system consolidation experience a plus.
• Strong background in cross-functional governance, executive reporting, and resource management, with exposure to corporate finance concepts (ROI, synergies, cost savings).

Technical Skills

• Atlassian suite: advanced proficiency with Jira Cloud and Confluence (boards, roadmaps/Plans, automation, reporting).
• Prioritization & metrics: fluency with RICE, weighted scoring, and value-vs-effort prioritization, plus Agile flow and delivery metrics.
• Reporting & analytics: Power BI/Jira Dashboards/Big Picture and Excel skills for portfolio dashboards and executive reporting.
• Architecture literacy: working understanding of APIs (REST/GraphQL), SSO, SCORM/AICC, headless/composable architecture, and integration/iPaaS patterns — enough to lead credibly, partner with engineering, and assess technical risk.
• AI fluency: practical familiarity with generative, predictive, and agentic AI in a delivery/PMO context, and the judgment to apply it responsibly.
• Methodologies: deep command of Agile, plus scaled frameworks (SAFe, LeSS) and Lean Portfolio Management; familiarity with MS Project / Visio / SharePoint useful.

Soft Skills

• Executive presence and the ability to facilitate difficult prioritization and trade-off discussions.
• Outstanding communicator, written and verbal, across technical and business audiences.
• Ability to influence without direct authority and drive alignment across diverse stakeholders.
• Strong facilitation, negotiation, and conflict-resolution skills.
• High adaptability, resilience, and comfort operating in ambiguous, fast-changing environments.
• Curiosity and a growth mindset — especially toward emerging tools and AI-enabled ways of working.

Benefits

• Competitive salary and annual bonus
• Flexible time off and company recognized holidays
• 401k Pension Plan with company match contributions
• Short-Term and Long-Term Disability
• Life Insurance- Basic, Voluntary, and AD&D
• Healthcare- Medical, Dental, Vision, and MDLive
• Flexible spending & Health Savings Accounts (HSA)
• Employee Assistance Program (EAP)

Why This Role Matters

This position sits at the intersection of strategy, technology, and execution. As 360training scales its platforms and integrates new acquisitions, the Portfolio / Strategic Projects Lead is the operational anchor who ensures the right initiatives are prioritized, delivered with discipline, and connected into a coherent digital ecosystem — supported increasingly by AI-enabled insight and governance.