PMO Strategic Projects Lead

360training

2d•Remote

About The Position

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 — stakeholder management, facilitation, and communication — needed to influence without direct authority.

Requirements

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.
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).
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.
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.

Nice To Haves

MBA preferred.
Change-management certification (e.g., PROSCI) a plus.
AI / data-related credentials or demonstrable applied experience a plus.
ERP / HR / Finance system consolidation experience a plus.
Familiarity with MS Project / Visio / SharePoint useful.

Responsibilities

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.
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.
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).
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.
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.
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.