Director, Program Management

Remote from: USA
Salary, yearly, USD: 119,300 - 371,300
Department: Product & Operations
Employment type: Full Time,
Job posted: 30 May 2026
Apply before: 30 Jun 2026
Experience level: Director
Views / Applies: 11 / 4

About company

About Five9

Empowering businesses to deliver exceptional customer experiences with cloud contact center solutions.

Computer Software
2001

Actively Hiring

AI Summary

Five9 seeks a Director of Program Management to lead the Business Technology organization's enterprise execution model. This strategic role involves redefining delivery capabilities, fostering a culture of excellence, and shifting focus from project completion to business impact. Key responsibilities include standardizing PM tools, establishing KPI frameworks, managing resource allocation, and serving as an escalation point. The ideal candidate is an outcome-driven leader with 8-12+ years of experience transforming PMOs in hyper-growth tech environments.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role requires extensive experience in PMO transformation, strategic thinking, and navigating ambiguity in a hyper-growth tech environment, making it highly challenging.

Salary Analysis

AI Insight The offered salary range of $119,300 to $371,300 is broad, with a median of $245,300, which is competitive for a Director-level PMO role in high-tech. The market range for similar roles is typically $150,000 to $300,000, so the upper end of the offer is attractive.

Key Skills

Program Management PMO Leadership Strategic Planning KPI Frameworks Resource Allocation Agile Methodologies Stakeholder Communication Risk Management Organizational Change Hyper-growth Tech

Cover Letter Sample

Dear Hiring Manager,

I am writing to express my strong interest in the Director of Program Management position at Five9. With over 10 years of experience leading enterprise PMOs in hyper-growth tech companies, I have a proven track record of transforming delivery models from compliance-focused to value-focused. I am particularly drawn to Five9's mission of bringing joy to customer experience and its team-first culture.

In my previous role, I successfully standardized project management processes, implemented KPI frameworks that measured business impact, and fostered a culture of strategic thinking among my team. I am confident that my experience in navigating ambiguity and driving organizational change aligns perfectly with the requirements of this role.

I am excited about the opportunity to redefine how Five9 delivers value and measures success. I look forward to contributing to the company's growth and helping to elevate its enterprise execution model. Thank you for considering my application.

Sincerely,
[Your Name]

Possible Interview Questions

Can you describe a time when you transformed a PMO from a compliance-focused to a value-focused organization?

In my previous role, I led a PMO transformation by shifting metrics from task completion to business impact. I implemented KPI frameworks that tracked ROI and user adoption, and I coached the team to act as strategic advisors rather than task administrators. This resulted in a 20% increase in on-time project delivery and improved stakeholder satisfaction.

How do you balance governance with agility in a hyper-growth environment?

I believe in right-sized governance that enables speed and accountability. I use a hybrid methodology where we apply lean principles for fast-moving initiatives and more structure for complex, high-risk projects. Regular retrospectives help us adjust the level of governance based on team feedback and project needs.

What experience do you have with resource allocation and capacity planning across a portfolio?

I have managed resource allocation for a portfolio of 50+ projects by using a combination of tools like Jira and Smartsheet to track capacity. I prioritize based on strategic value and resource availability, and I hold regular capacity reviews with functional leads to adjust as needed. This approach reduced resource conflicts by 30%.

How do you measure the success of a PMO beyond project completion?

I define success by business impact, such as user adoption rates, cost savings, revenue growth, or customer satisfaction improvements. I work with stakeholders to set these metrics at the start of each initiative and track them post-launch. For example, after a CRM implementation, we measured a 15% increase in sales productivity.

Describe a situation where you had to navigate ambiguity and make a decision with incomplete information.

During a major system migration, we faced unclear requirements and shifting priorities. I facilitated a workshop with key stakeholders to align on a minimum viable scope and set a 60-day timeline. I empowered the team to make decisions within that scope and communicated trade-offs transparently. The migration was completed on time with minimal disruption.

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.

Key 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.

Qualifications

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.

Experience

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.

As part of our continued commitment to diversity, equity, and inclusion, Five9 supports pay transparency during the entire recruitment process. Actual compensation packages are based on several factors that are unique to each candidate including, but not limited to: skill set, depth of experience, certifications, and specific work location. The range displayed reflects the minimum and maximum target for new hire salaries for the job across the United States. Your recruiter can share more about the specific compensation package during your hiring process.

Additionally, the total compensation package for this position may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Our total reward package also includes:

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. We also offer Short & Long-Term Disability, Basic Life Insurance, and a 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 and 12 weeks paid parental leave.

All compensation and benefits are subject to the requirements and restrictions set forth in the applicable plan documents and any written agreements between the parties.

The US base salary range for this role is below.

$119,300—$371,300 USD

Five9 embraces diversity and is committed to building a team that represents a variety of backgrounds, perspectives, and skills. The more inclusive we are, the better we are. Five9 is an equal opportunity employer.

View our privacy policy, including our privacy notice to California residents here: https://www.five9.com/pt-pt/legal.

Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.

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