PMO Strategic Projects Lead

360training

At 360training, we’re more than an online training provider—we’re on a mission to empower people and organizations to thrive. As a fast-growing leader in online and live training across multiple industries, we deliver regulatory-approved training and certifications that power careers and businesses.

Our culture is grounded in two values: Deliver Results and Do the Right Thing. We operate as a collaborative, performance-driven organization where data plays a critical role in shaping strategy and outcomes. If you’re excited to turn analytics into impact and influence meaningful decisions, 360training is the place for you.

This is a remote position and we are looking to hire in the following states:

AZ, FL, GA, LA, NJ, PA, TN, TX, UT, ID, MI, MO and WI

THERE IS NO VISA SPONSORSHIP FOR THIS ROLE

PMO Strategic Projects Lead

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.

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

Education \& Certifications * 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.

Experience * 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.

We Offer Great 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