Sr. Director, Global Technology PMO Leader

Position Overview

The Global Technology PMO Leader is a senior technology leader within IT Enterprise Services (ITES), accountable for building and scaling a global, value-driven Technology Portfolio Management Office that spans multiple technology domains within Direct Travel: Travel Operations, Infrastructure, Security, and Enterprise Services.

This role owns the Technology PMO operating model, evolving the IT Enterprise Services Value Driven Portfolio Model into a single enterprise framework that standardizes how technology work is intaken, prioritized, funded, governed, delivered, and measured against defined value drivers, while tailoring standards to the distinct needs of each domain.

The leader runs a global organization of Program Managers, Atlassian Technical Analyst, and leads through data: using the Atlassian platform, automation, and AI to replace manual status gathering with real-time portfolio insight and executive-ready reporting for the SVP of ITES, the CIO, and the Executive Leadership Team.

This is a leader who operates comfortably at both the strategic and hands-on level, setting portfolio and reporting strategy while stepping directly into business-critical programs when needed.

Responsibilities

Global Portfolio Strategy & PMO Standards

• Own and evolve the Global Technology PMO operating model, extending a Value Driven Portfolio Model into a unified framework across Technology Operations, Infrastructure, Security, and Enterprise Services.
• Define and continuously mature PMO standards for each technology domain (e.g., change and release coordination for Operations, lifecycle and capacity planning for Infrastructure, risk and control alignment for Security, product and platform delivery for Enterprise Services) on top of a common intake, prioritization, and reporting backbone.
• Lead technology intake and portfolio prioritization, aligning investment to defined Value Drivers (Revenue Growth, Increased Efficiency, Customer/Employee Retention, Risk & Compliance, Foundation/Tech Debt) and facilitating decision forums where business and technology leaders resolve competing priorities and capacity conflicts.
• Establish governance cadences, stage gates, and delivery artifacts (charters, cost/benefit analysis, RAID logs, status reporting) across the Intake, Review, Assess & Architect, Analyze & Decide, Delivery, and Measure & Iterate lifecycle, while adhering to an Agile methodology.
• Manage portfolio-level capacity, dependencies, and financials (budget vs. actuals, CapEx/OpEx) across global teams, regions, and time zones, proactively surfacing and resolving cross-program risks.

Agile Delivery Framework

• Own and evolve the technology organization's Agile delivery framework, defining a common, right-sized model (Scrum, Kanban, and hybrid/waterfall where appropriate) with consistent ceremonies, roles, and artifacts across Operations, Infrastructure, Security, and Enterprise Services.
• Lead quarterly planning and cross-team release coordination (e.g., PI or quarterly planning, dependency management, and release readiness) so global teams plan together, deliver predictably, and stay aligned to portfolio priorities.
• Measure and coach Agile maturity using delivery metrics such as velocity, cycle time, predictability, and flow, and lead Agile coaching and training so teams continuously improve how they deliver.

Executive Reporting, Automation & AI

• Own executive technology portfolio reporting, including the CIO Key Initiatives monthly update and ELT-level briefings, as the single source of truth for program health, milestones, risk, spend, and value realized.
• Lead a reporting-by-automation model: replace manual status collection with automated, self-service dashboards sourced directly from systems of record such as Jira, Jira Service Management, Confluence, and service desk platforms.
• Define and track PMO and portfolio KPIs (e.g., on-time delivery, throughput, intake cycle time, capacity utilization, value realized, benefits tracking) and use them to drive continuous improvement and investment decisions.
• Apply AI and automation to PMO workflows, such as automated status summaries, risk and slippage detection, intake triage, and executive briefing generation, within appropriate data governance and responsible-AI guardrails.
• Direct the Atlassian Technical Analyst, in partnership with Jira administration, to design and maintain a standardized global Atlassian portfolio architecture (projects, workflows, hierarchies, templates, roadmaps, and Confluence spaces) that embeds PMO standards into the tools.

People Leadership & Delivery Oversight

• Lead, coach, and develop a global organization of Program Managers and an Technical Analysts, including workload and capacity planning, performance management, values adoption, leader development, succession, and career growth.
• Directly lead or provide oversight of business-critical, cross-functional technology programs (e.g., platform consolidation, M&A integration, security and compliance initiatives), stepping in as needed to ensure successful delivery.
• Partner closely with Architecture, Product Management, Business Engagement, Security, Infrastructure, and Operations leaders to remove roadblocks and elevate delivery maturity across the technology organization.
• Champion change management and communication for the PMO operating model and reporting standards, driving consistent adoption across global teams and stakeholders.

Basic Qualifications

• Bachelor's degree plus 12+ years of experience in technology program, portfolio, or project management, including 6+ years leading a PMO or portfolio function and managing managers or other leaders
• Demonstrated success building or scaling a technology PMO that spans multiple domains (e.g., infrastructure, operations, security, enterprise applications), with governance, intake, and value-based prioritization models.
• Experience leading global, distributed teams and portfolios across multiple regions and time zones.
• Proven track record delivering executive and ELT-level portfolio reporting, including building automated, data-driven dashboards that replaced manual reporting.
• Deep hands-on experience using the Atlassian platform (Jira, Confluence, Jira Service Management) as a portfolio management and reporting system, including portfolio planning tools such as Advanced Roadmaps or Jira Align.
• Experience sponsoring or overseeing enterprise-wide transformation programs that span business and technology, such as service transformation, M&A integration, or platform consolidation.
• Practical understanding of how AI and automation can be applied to portfolio management and reporting, including data quality and responsible-AI considerations.
• Proven experience designing and implementing an Agile delivery framework across multiple teams, including Scrum, Kanban, and hybrid/waterfall models, scaled planning across teams (e.g., SAFe PI planning), and improving Agile maturity through coaching and delivery metrics.
• Executive presence with excellent communication, influencing, and conflict-resolution skills; able to drive alignment among senior business and technology leaders.
• Strong financial and analytical acumen, including portfolio budgeting, CapEx/OpEx tracking, and benefits realization.
• Demonstrated ability to lead organizational change and drive adoption of new operating models, standards, and tools.

Preferred Qualifications

• PMP, PgMP, or PfMP certification; SAFe SPC or Lean Portfolio Management (LPM) certification.
• ITIL 4 certification or experience aligning PMO practices with IT service management (change, release, and problem management).
• Atlassian certifications, or experience with Atlassian Analytics, Jira Align, or AI capabilities such as Atlassian Rovo.
• Experience deploying generative AI or copilot tools (e.g., Microsoft Copilot, Atlassian Rovo) for reporting or portfolio management use cases.
• Experience with BI and visualization tools such as Power BI or Tableau.
• Experience supporting security and compliance programs (e.g., SOC 2, ISO 27001, PCI DSS).
• Experience in travel, hospitality, or global services organizations, ideally within a Salesforce-centric and contact-center-enabled environment.
• Experience leading portfolios through M&A integration or platform consolidation.

Benefits Summary

In addition to Medical, Dental, and Vision benefits Direct Travel offers a Total Rewards Package which includes Retirement Plans, Wellness, Rewards and Recognition, Sustainability, DE&I initiatives, and Mental Health Support.

About Direct Travel

Direct Travel is one of the world’s largest travel management companies. With a long history of proven market expertise, we blend advanced technology, superior service, and expert insight to drive tangible value and meaningful savings across Corporate Travel, Leisure Travel, Meetings & Events and specialty travel businesses. Through Avenir, our intelligent travel management platform, we reduce obstacles and give clients more direct access to content, trusted data, intelligence and global expertise. What truly sets us apart is the human care behind the technology, delivered by an experienced, passionate team dedicated to anticipating needs and delivering exceptional service at every step. For more information about Direct Travel, visit www.dt.com

Direct Travel is an equal opportunity employer

#LI-Remote