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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 Management to 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 50 mile radius of our San Ramon office. For candidates who reside within 50 miles of our San Ramon location, this role is Hybrid and would require 3 days a week (M, W, TH) in our San Ramon 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.
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.
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Note: Five9 will never request that an applicant send money as a prerequisite for commencing employment with Five9.