Senior Director, Project Management Office

The Senior Director, Project Management Office is responsible for establishing and leading the Customer Success portfolio management and project delivery discipline. This role will create governance, standards, operating rhythms, tools, and executive visibility required to translate CSLT priorities into coordinated, well-managed programs and projects.

The Senior Director will oversee portfolio intake, prioritization support, integrated planning, resource and capacity visibility, dependency management, risk and issue escalation, and consistent delivery reporting across Customer Success and cross-functional initiatives. Working closely with CSLT members and business partners, this leader will strengthen accountability, improve predictability, and ensure leadership decisions are grounded in clear facts, trade-offs, and delivery implications.

What You Will Work On:

Strategic Portfolio Management

• Build and maintain the integrated Customer Success portfolio, connecting strategic priorities to approved programs, projects, accountable owners, targeted outcomes, and delivery timelines.

• Establish a transparent intake and governance process for evaluating, approving, sequencing, pausing, and closing initiatives.

• Facilitate portfolio prioritization by providing fact-based analysis of value, urgency, risk, capacity, dependencies, customer impact, and strategic alignment.

• Support CSLT in making explicit trade-offs so resources remain focused on the highest-priority work

Program and Project Delivery Excellence

• Define scalable project and program management standards, templates, stage gates, controls, and delivery expectations appropriate to the size and risk of each initiative.

• Provide direct program leadership for the most complex, cross-functional, or strategically critical initiatives and assign or guide project management resources where needed.
• Ensure every initiative has a clear charter, sponsor, accountable business owner, scope, roadmap, milestones, decision rights, success measures, and closure criteria.

• Drive disciplined management of scope, schedule, resources, dependencies, assumptions, risks, issues, decisions, and corrective actions.

Governance and Executive Reporting

• Design and facilitate portfolio and program governance forums that accelerate decisions, remove obstacles, and reinforce accountability.

• Create concise, executive-ready reporting that distinguishes delivery status, business outcome progress, adoption status, material risks, decisions required, and changes to forecast.

• Maintain a single source of truth for the portfolio and ensure status information is timely, consistent, and evidence based.

• Escalate risks, capacity constraints, unresolved dependencies, and decision delays early, with clear options and recommendations.

Resource, Capacity, and Dependency Management

• Develop portfolio-level visibility into resource demand, available capacity, critical skills, timing conflicts, and cross-functional constraints.

• Partner with CSLT and Finance to support investment planning, business cases, budget readiness, and resource allocation decisions.

• Identify dependencies across Customer Success, Product, Technology, Sales, Support, Operations, Finance, and other partners, and establish owners and resolution plans.

• Recommend sequencing, resourcing, or scope adjustments when the portfolio exceeds organizational capacity.

PMO Capability and Team Leadership

• Build, lead, coach, and develop project and program management talent, creating clear expectations for quality, accountability, and stakeholder partnership.

• Establish a fit-for-purpose PMO model that balances governance with speed and avoids unnecessary bureaucracy.

• Create reusable tools, playbooks, training, and communities of practice that strengthen project management capability across Customer Success.

• Continuously improve PMO practices using delivery data, stakeholder feedback, retrospectives, and lessons learned.

Customer and Business Outcomes

• Ensure the portfolio remains connected to customer retention, customer experience, operational performance, growth, colleague effectiveness, and strategic commitments.

• Partner with the Senior Director, Customer Success Transformation to connect future-state design and adoption requirements to executable roadmaps and governed delivery plans.

• Promote a culture of no surprises, fact-based decision-making, disciplined execution, and continuous improvement.

What You Will Bring (qualifications)

• Bachelor's degree in Business, Engineering, Operations, Information Systems, or a related field; advanced degree preferred.

• 10+ years of progressive experience in portfolio, program, project, operations, or transformation leadership, including at least 5 years in a leadership role.
• Proven experience building or leading an enterprise or functional PMO and managing a portfolio of complex, cross-functional initiatives.

• Demonstrated command of portfolio governance, prioritization, integrated planning, dependency management, risk management, resource capacity analysis, and executive reporting.

• Strong business judgment with the ability to translate strategy into executable plans and surface clear trade-offs and recommendations.

• Excellent leadership, stakeholder management, facilitation, communication, and executive presentation skills.

• Experience in enterprise software, SaaS, technology-enabled services, customer operations, or management consulting preferred.

• PMP, PgMP, PfMP, or comparable certification preferred.

Key Competencies

• Strategic Portfolio Management

• Program and Project Delivery Leadership

• Governance and Decision Facilitation

• Resource and Capacity Management

• Risk, Issue, and Dependency Management

• Executive Communication and Influence

• Data-Driven Decision-Making

• Team Leadership and Capability Building

Role Boundary

This role owns the governance and delivery system for the portfolio. It does not own Voice of the Customer strategy, future-state process or operating-model design, organizational change content, CS enablement strategy, or adoption outcomes. Those responsibilities sit with the Senior Director, Customer Success Transformation, in partnership with functional business owners.