Director, Program Management
About The Position
Five9 is seeking a Director, Program Management to join the Business Technology (BT) organization to elevate our enterprise execution model. This 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.
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.
- 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.
Nice To Haves
- 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.
Responsibilities
- Standardize and implement project management tools, processes, and operating rhythms to enhance consistency and clarity.
- Establish repeatable communication strategy frameworks for stakeholders that provide transparency on project health, progress, risks, and outcomes.
- Develop and implement sophisticated KPI frameworks that measure execution quality, delivery performance, value realization, and business impact.
- Manage project and program management capacity planning, resource allocation strategy, and prioritization across the entire BT portfolio.
- Define end-to-end delivery standards, including stakeholder alignment, scope definition, planning discipline, technical feasibility validation, resource planning, budgeting, milestone tracking, and timeline management.
- 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.
Benefits
- Health, dental, and vision coverage, beginning on the first day of employment.
- Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
- Short & Long-Term Disability
- Basic Life Insurance
- 401k saving plan with employer matching.
- Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
- Generous employee stock purchase plan.
- Paid Time Off
- Company paid holidays
- Paid volunteer hours
- 12 weeks paid parental leave.
- Annual performance bonus
- Stock
- Other applicable incentive compensation plans.
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What This Job Offers
Job Type
Full-time
Career Level
Director
Education Level
No Education Listed
