Senior Project Manager

Five9•Irving, TX

9h•Hybrid

About The Position

Five9 is seeking an experienced Senior Project Manager to lead complex, cross-functional business technology initiatives from concept through delivery. The role manages multiple concurrent projects across enterprise platforms, including CRM, HCM/HRIS, marketing automation, AI/automation, workforce management, and other systems supporting revenue growth, operational scale, compliance, efficiency, and security. The ideal candidate combines disciplined project leadership with business and technical acumen and can influence stakeholders in a fast-paced, global environment. The role also emphasizes continuous improvement and delivering business value. The Senior Project Manager owns delivery governance and coordinates stakeholders across business and technical teams. They lead planning, requirements, testing, release, change management, and adoption, while communicating project status, decisions, risks, financials, and outcomes. They are expected to use AI to automate routine project management activities and share useful approaches with the PMO. This is a hybrid role requiring three days per week (Tuesday, Wednesday, and Thursday) in Five9’s Dallas office. The US base salary range is $104,700–$291,200. Total compensation may also include an annual performance bonus, stock, and/or other applicable incentive compensation plans.

Requirements

At least 5 years of prior project or program management experience is preferred, delivering enterprise software, SaaS, cloud, or business systems initiatives from start to finish.
Experience managing multiple workstreams, cross-functional teams, third-party vendors, budgets, and senior stakeholder expectations.
Demonstrated success delivering complex, cross-functional technology initiatives on time, within scope, and within budget.
Strong leadership, facilitation, negotiation, and influencing skills, including the ability to drive alignment without direct authority.
Sound judgment and analytical problem-solving skills, with the ability to prioritize competing demands and make tradeoffs in a dynamic environment.
Working knowledge of multiple delivery approaches, such as Agile, Scrum, Waterfall, or hybrid, and judgment to apply the appropriate method.
Ability to translate business needs into technical requirements or user stories while focusing on outcomes and user adoption.
Executive-level written and verbal communication skills and a proactive, accountable, collaborative working style.
Curiosity about AI and eagerness to use it to automate routine project management work and improve efficiency.

Nice To Haves

Experience with enterprise platforms such as CRM, HCM/HRIS, marketing automation platforms, AI/automation, workforce management, integration and automation tools, or ERP systems.
PMP, PMI-ACP, Certified ScrumMaster, or comparable project management or agile certification.
Experience with multiple delivery models, such as waterfall, hybrid, blended, spiral, agile, SAFe, and Kanban.
Experience with AI projects or AI tools, including examples of using AI to remove routine work.

Responsibilities

Own end-to-end delivery of multiple complex, concurrent business technology projects, from intake and planning through implementation, adoption, and closeout.
Partner with business leaders, product owners, engineering teams, architects, vendors, and other stakeholders to align objectives, scope, success measures, dependencies, and delivery commitments.
Develop and maintain project charters, integrated plans, schedules, budgets, resource forecasts, decision logs, risk and issue registers, and executive-ready status reporting.
Own delivery governance, facilitate key decisions, and manage changes to scope, schedule, resources, and priorities while assessing business and delivery impacts.
Run monthly steering committees and weekly status reviews, manage RAID, and coordinate user acceptance testing.
Identify risks, issues, and cross-project dependencies; establish mitigation and escalation plans; and remove obstacles to keep delivery on track.
Diplomatically challenge requests that put scope, quality, or dates at risk and offer options and tradeoffs.
Lead requirements and user stories, readiness, testing, release, and change-management activities with business and technical teams to support adoption.
Communicate concise, transparent updates on progress, milestones, decisions, risks, financials, and outcomes to working teams and senior leaders.
Use AI to automate routine project management activities, improve efficiency, and share approaches with the PMO.
Improve project management practices through lessons learned, reusable standards, delivery metrics, and continuous improvement across the PMO.

Benefits

Annual performance bonus, stock, and/or other applicable incentive compensation plans may be included in total compensation.
Health, dental, and vision coverage beginning on the first day of employment; Five9 covers 100% of the employee portion and shares a high portion of dependent costs.
Short- and long-term disability insurance.
Basic life insurance.
401(k) savings plan with employer matching.
Mental health support platform offering therapy, coaching, and self-guided mindfulness resources for covered employees and dependents.
Employee stock purchase plan.
Paid time off.
Company-paid holidays.
Paid volunteer hours.
12 weeks of paid parental leave.