Director, Program Management

Director, Program Management

Five9 is a leading provider of cloud contact center software, dedicated to enhancing customer experiences through cloud innovation. We foster a team-first culture that celebrates diversity, inclusion, and empowers employees to be their authentic selves.

About the Role

We are seeking an experienced Director, Program Management to join our Business Technology (BT) organization. This is a strategic role focused on elevating our enterprise execution model, redefining how we deliver value, measure success, and drive business impact. You will be instrumental in maturing our delivery capabilities and cultivating a culture of excellence.

Key Responsibilities

• Lead, coach, and empower the project management team, fostering high performance and strategic thinking.
• Spearhead the implementation of best practices across delivery processes, establishing a framework for repeatability, clarity, and consistency in BT initiatives.
• Ensure projects are executed with discipline and predictability.
• Redefine success metrics to focus on business impact, user adoption, and Return on Investment (ROI).
• Standardize and implement project management tools, processes, and operating rhythms.
• Establish repeatable communication strategy frameworks for stakeholders, ensuring transparency on project health, progress, risks, and outcomes.
• Develop and implement sophisticated KPI frameworks to measure execution quality, delivery performance, value realization, and business impact.
• Manage project and program management capacity planning, resource allocation, and prioritization across the BT portfolio.
• Define end-to-end delivery standards, including stakeholder alignment, scope definition, planning, technical validation, resource planning, budgeting, milestone tracking, and timeline management.
• Serve as an escalation point for the PMO team to proactively manage risks, dependencies, and blockers.
• Partner with senior BT leadership to drive continuous improvement across the delivery lifecycle.
• Provide proactive, concise, and strategic insights into portfolio health, risks, trade-offs, and cross-functional dependencies.

Requirements

• Strategic thinker with strong operational execution capabilities.
• Experience 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.
• 8–12+ years of experience 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, including leading global team members.

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.
• Scalable, right-sized governance that enables speed and accountability.
• Standardized, repeatable playbooks driving consistent execution excellence.
• Delivery success defined by business impact.
• Thoughtful adoption of agile, hybrid, and adaptive methodologies.

What We Offer

• Compensation: The US base salary range for this role is $119,300—$371,300 USD. Actual compensation will depend on factors such as skill set, experience, certifications, and location. The total compensation package may also include an annual performance bonus, stock, and/or other incentive compensation plans.
• Health & Wellness: Comprehensive health, dental, and vision coverage starting on day one, with Five9 covering 100% of employee premiums. Short & Long-Term Disability, Basic Life Insurance, and a 401k saving plan with employer matching. Access to an innovative mental health support platform.
• Work-Life Balance: Generous Paid Time Off, company-paid holidays, paid volunteer hours, and 12 weeks of paid parental leave.
• Equity: Generous employee stock purchase plan.
• Work Location: This role is fully remote for candidates residing outside a 30-mile radius of a Five9 office. For those within a 30-mile radius, the role is hybrid, requiring 3 days per week in office.

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. We are an equal opportunity employer.