Senior PMO Lead/Director

Company Overview

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.

Our seasoned professionals deliver services based on Milestone's best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Job Overview

As Senior PMO Lead / Director, you will have critical strategic leadership responsibility for building and operating PM/PMO-as-a-Service within a Global Business Services (GBS) organization. This is not just corporate PMO governance, you'll run a professional service that internal customers choose based on quality, responsiveness, and demonstrated value and Project Managers are proud to be part of.

You'll partner with our Principal Transformation Consultant during design and implementation phases, progressively assuming operational accountability before taking full ownership of the established capability. This senior leadership position demands someone who can balance rigorous governance with exceptional customer service while building and leading high-performing teams.

Phased Engagement Model

Phase 1 (Months 1-6): Shadow and Learn

• Participate in transformation design activities
• Build relationships with executive stakeholders and functional leaders
• Understand design rationale and organizational dynamics
• Begin building operational team foundation

Phase 2 (Months 7-10): Co-Lead and Transition

• Assume increasing operational accountability
• Lead service delivery while Principal Consultant focuses on knowledge transfer
• Take ownership of stakeholder relationships and performance management
• Prepare for independent operation with quarterly advisory support

Phase 3 (Month 11+): Full Operational Leadership

• Complete accountability for PMO-as-a-Service operations and performance
• Manage portfolio governance and executive relationships
• Drive continuous improvement and capability maturation

Key Responsibilities

Service Delivery Excellence:

• Operate PMO-as-a-Service with service catalogue, transparent cost management, and customer satisfaction focus
• Balance rigorous governance standards with responsiveness and stakeholder experience
• Develop and maintain activity-based costing model supporting chargeback mechanisms
• Manage service levels, performance metrics, and continuous improvement programs

Portfolio Governance and Strategic Alignment:

• Drive enterprise PMO governance frameworks to ensure consistency, transparency, and accountability across all projects and programs
• Align project portfolios with organizational strategic objectives and ethical values, ensuring initiatives deliver measurable business outcomes
• Provide executive leadership with clear, concise insights on portfolio status, risks, resource capacity, and value realization
• Ensure compliance with regulatory, financial, and organizational governance requirements

Vendor and Workforce Strategy:

• Lead vendor management strategy supporting internalization targets through data-driven performance evaluation
• Manage transition from external contractors to internal capability building (supporting internalization goal)
• Oversee systematic quality monitoring and vendor accountability using objective performance data
• Optimize resource allocation balancing internal capability development and strategic contractor use

Technology and Innovation Leadership:

• Oversee enterprise PMO platform operations and prepare for future platform migrations
• Champion AI-enhanced project management and portfolio intelligence while ensuring governance compliance
• Work with technical teams to identify high-value automation and analytics opportunities
• Maintain platform-independent business logic enabling future technology transitions

Team Development and Cross-Functional Collaboration:

• Mentor and develop PMO leadership and project teams, fostering a culture of excellence, ethical conduct, and shared success
• Lead cross-functional collaboration with HR, IT, Transformation, and Change Management functions to embed best practices
• Manage stakeholder engagement at senior executive level, driving alignment, prioritization, and informed decision-making
• Champion continuous improvement programs within the PMO to optimize efficiency, agility, and scalability

Qualifications

Experience and Leadership:

• Over 10 years of progressive experience in PMO leadership roles, managing enterprise-level portfolios and large-scale transformations
• Proven ability to lead, upskill and mature project and program management professionals
• Experience in shared services or Global Business Services (GBS) environments with service delivery and customer satisfaction accountability
• Deep expertise in PMO governance, portfolio management, and strategic alignment frameworks
• Proven ability to influence and collaborate with C-suite executives and senior stakeholders

Technical and Business Expertise:

• Extensive knowledge of project management methodologies (Agile, Waterfall, hybrid) and advanced analytics for performance measurement
• Understanding of activity-based costing, service catalogue development, and pricing models
• Experience with vendor management, workforce planning, and contractor-to-employee transitions
• Familiarity with enterprise PMO platforms and integration strategies

Cultural and Professional Qualifications:

• Strong leadership skills, with a track record of building high-performing teams and driving cultural change
• Experience integrating change management with project delivery for maximum adoption and business impact
• Advanced degree in Business, Project Management, IT, or related fields preferred; professional certifications (PMP, PgMP, Agile, Prosci) highly desirable
• Commitment to ethical leadership and fostering an inclusive, people-first culture

Why Milestone?

• Lead the strategic helm of a purpose-driven organization committed to innovation and sustainable impact.
• Influence transformative initiatives that improve global health and community wellbeing.
• Access to executive development opportunities within a transparent and collaborative culture.
• Competitive senior leadership compensation and benefits reflecting your influence and experience.

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Compensation

Estimated Pay Range:

Exact compensation and offers of employment are dependent on circumstances of each case and will be determined based on job-related knowledge, skills, experience, licenses or certifications, and location.

Our Commitment to Diversity & Inclusion

At Milestone we strive to create a workplace that reflects the communities we serve and work with, where we all feel empowered to bring our full, authentic selves to work. We know creating a diverse and inclusive culture that champions equity and belonging is not only the right thing to do for our employees but is also critical to our continued success.

Milestone Technologies provides equal employment opportunity for all applicants and employees. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race, color, religion, gender, gender identity, marital status, age, disability, veteran status, sexual orientation, national origin, or any other category protected by applicable federal and state law, or local ordinance. Milestone also makes reasonable accommodations for disabled applicants and employees.

We welcome the unique background, culture, experiences, knowledge, innovation, self-expression and perspectives you can bring to our global community. Our recruitment team is looking forward to meeting you.