Serve as an escalation point for PMO team members to proactively manage risks, dependencies, and blockers.
Partner with senior BT leadership to drive continuous improvement across the delivery lifecycle.
Deliver proactive, concise, and strategic insights into overall portfolio health, risks, trade-offs, and cross-functional dependencies.
Requirements
Strategic thinker with strong operational execution capabilities.
Experienced navigating ambiguity, scale, and organizational change.
Demonstrated ability to balance governance with agility.
Data-driven decision-maker with strong analytical instincts.
Proven leader with the ability to coach, develop, and elevate a team.
Leadership Mindset
Outcome-driven rather than process-driven.
Operates as an enabler and strategic partner - not a gatekeeper.
Comfortable making decisions amid ambiguity and evolving priorities.
Knows when to apply structure and when to accelerate with urgency.
Passionate about evolving delivery models from compliance-focused to value-focused.
What Success Looks Like
Clear, transparent portfolio visibility with proactive risk management.
Improved predictability in delivery timelines and outcomes.
A PM team operating as strategic advisors, not task administrators.
Scalable, right-sized governance that enables speed and accountability.
Standardized, repeatable playbooks that drive consistent execution excellence.
Delivery success defined by business impact - not task completion.
Thoughtful adoption of agile, hybrid, and adaptive methodologies where they best fit.
8-12+ years leading enterprise delivery, PMO, or portfolio management functions.
Proven experience in transforming a PMO in hyper-growth, high tech organizations.
Strong background in agile, hybrid, and scaled delivery models.
Proven track record managing cross-functional programs in hybrid/agile environments.
People management experience leading global team members.
Work Location: This role is fully remote for candidates who reside outside the 30 mile radius of one of our offices. For candidates who reside within a 30 mile radius of one of our offices, this role is Hybrid and would require 3 days a week (T, W, TH) in office.
Additional Information
Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.
Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves.
We are seeking a Director, Program Managementto join the Business Technology (BT) organization to elevate our enterprise execution model. This is not a traditional PMO leadership role focused solely on process; it is a strategic opportunity to redefine how we deliver value, measure success, and drive business impact. You will be at the forefront of maturing our delivery capabilities and fostering a culture of excellence.
In this role, you will lead, coach, and empower our project management team, fostering a culture of high performance and strategic thinking. You will spearhead the implementation of best practices across our delivery processes, establishing a framework that drives repeatability, clarity, and consistency for all BT initiatives. A key component of your leadership will be to ensure projects are executed with discipline and predictability. Ultimately, you will redefine our success metrics, shifting the focus from simple project completion to measuring the true business impact, user adoption, and ROI our work delivers.
Five9 · US