Senior Delivery Manager

The team
The Delivery Management Team at Five9 is responsible for orchestrating the delivery and release of software with precision and agility, leveraging best practices, tools and technologies to ensure seamless integration, rapid deployment, and unwavering quality. This team is committed to fostering a collaborative environment that prioritizes continuous improvement and customer satisfaction, driving forward the success of our organization and our clients. This is a highly visible team across the board due to the nature of work and the opportunities to engage with all departments within Five9 to deliver a quality software rollout experience to internal and external customers/stakeholders.

Role purpose
The purpose of this role is to manage and optimize the end-to-end process of software delivery and release management. Senior Delivery Manager is a pivotal role within Five9 as we rely heavily on regular software rollouts to production. The individual in this role as a strategic leader ensures the
smooth delivery of products while managing the complexities and risks inherent in the release process, and that releases are executed efficiently, and any potential issues are getting addressed proactively to minimize disruptions to business operations. This role is essential for maintaining the agility of the company while ensuring the quality and reliability of software products.

How you contribute

• End-to-End Delivery Management:
  • Define and implement release schedules, ensuring that deadlines and business needs are met.
  • Manage the release pipeline and coordinate the activities of development, QA, operations, and support teams and ensure that each release is thoroughly certified and delivered on time.
  • Oversee the full release lifecycle, from planning and development to deployment and post- release support.
• Strategic Planning and Execution:
  • Work closely with product management, engineering, and stakeholders to prioritize content for releases based on business objectives and customer impact.
  • Ensure all releases align with the broader strategic goals of the business, ensuring that new features, enhancements, and bug fixes are properly integrated into the release cycle.
  • Proactively identify risks and potential bottlenecks in the release process and develop mitigation strategies, providing timely resolutions to minimize disruptions to the business.
  • Partner with the Delivery Management team and vertical teams to align on and implement release process improvements.
• Collaboration and Stakeholder Communication:
  • Serve as the main point of contact for all stakeholders involved in the release process, including senior leadership, product owners, engineering teams, operations teams, customer support.
  • Communicate progress, blockers, and risks to stakeholders at all levels, ensuring everyone is informed and aligned.
  • Provide regular updates on the status of releases and the impact of upcoming changes to business operations.
• Continuous Improvement:
  • Analyze the effectiveness of each release, identifying opportunities for process improvement, automation, and risk reduction.
  • Drive the adoption of industry best practices in release management, ensuring that releases are more efficient and predictable over time and delivers real value to end customers.
  • Establish and track key performance indicators (KPIs) and metrics related to release cycles, such as release frequency, deployment success rates, and post-release defect rates and drive meaningful actions.
• Change Management and Tool Optimization:
  • Ensure that all changes to production systems are properly documented, tracked, and managed according to best practices.
  • Oversee version control and configuration management processes to maintain consistency and traceability across releases.
  • Manage and optimize release management toolkit (e.g., Jira, GitLab, Launch Darkly, etc.) to support an efficient release pipeline.
  • Identify opportunities for automation in the release process, reducing manual intervention and increasing speed and reliability.

Skills, competencies and qualifications
Required:

• 7+ years related work experience.
• Proven ability to lead and inspire cross-functional teams in complex and fast-paced environments.
• Strong collaboration skills to work effectively across multiple teams and departments.
• Deep understanding of the software development lifecycle (SDLC), particularly in continuous integration, continuous delivery (CI/CD), and release management.
• Strong organizational and time-management skills, with experience in managing multiple releases simultaneously.
• Expertise in Agile, Scrum, or other project management methodologies to plan, track, and execute releases efficiently.
• Demonstrated track record of proactively surfacing and resolving risks before they escalate, rather than managing issues only as they arise, backed by strong analytical judgment.
• Ability to resolve issues under pressure, maintaining a calm and solution-oriented approach with very little guidance
• Excellent communication skills to articulate complex technical concepts to both technical and non-technical stakeholders.
• Ability to manage expectations, negotiate timelines, and ensure all parties are aligned on release goals and outcomes.
• Connects release and delivery decisions to business and customer outcomes, not just process execution.
• Proven experience across both release and delivery management, with the ability to quickly apply that experience to Five9’s environment.
• Proven track record of leading a release process improvement or change initiative that measurably reduced risk, defects, or delivery time.
• Adaptable and growth-oriented, comfortable operating in a fast-evolving environment.
• Bachelor’s degree (or equivalent) in relevant discipline.

Desirable:

• Proven track record of building mutually beneficial relationships at all levels.
• A focus on metrics-driven improvement, with a proven track record of refining processes and increasing efficiency over time.
• Customer focused, action and results orientated with an alignment to our Values.

Key Stakeholders

• Engineering Service Owners
• Product Managers
• Customer Support and Technical Account Management groups
• Engineering Operations, Program Managers and Production Support teams