Senior Delivery Operations & Enablement Director

Priceline.com•New York, NY

43d•Hybrid

About The Position

The Senior Delivery Operations & Enablement Director is a senior operational leader accountable for optimizing the technology and product delivery operating model-driving excellence, consistency, and scalability across portfolios. This role defines the frameworks, insights, and enablement platforms that power the effectiveness of engineering and product teams. This leader operates as a force multiplier-establishing the practices, data systems, and cultural habits that elevate delivery performance and developer experience across the enterprise. While not directly managing delivery teams, this role requires deep operational leadership, systems thinking, and strong influence across senior engineering, product, and finance stakeholders. The ideal candidate brings expertise in production operating model design and optimization, with a track record of enabling tech and product organizations to deliver faster, more predictably, and with higher quality.

Requirements

10+ years of experience in technology delivery, engineering operations, or large-scale product development.
Proven experience designing and optimizing delivery operating models in scaled tech or digital organizations.
Deep expertise in Agile, Lean Portfolio Management, and DevOps frameworks, with practical experience applying them across multi-team environments.
Strong proficiency with delivery and productivity analytics tools (e.g., JIRA, ADO, Power BI/Tableau, developer productivity telemetry).
Demonstrated ability to translate operational data into business insights and drive executive decision-making.
Experience developing and implementing training, enablement, and maturity uplift programs for technical organizations.
Excellent communication, facilitation, and influencing skills-comfortable engaging at all levels, from engineers to C-suite.
Strategic mindset with strong operational rigor-able to move fluidly between conceptual design and execution.
Illustrated history of living the values vital to Priceline: Customer, Innovation, Team, Accountability and Trust.
The Right Results, the Right Way is not just a motto at Priceline; it's a way of life. Unquestionable integrity and ethics is essential.

Nice To Haves

Experience standing up a delivery center of excellence in a scaled tech enterprise.
Familiarity with engineering productivity frameworks (e.g., SPACE, DORA) and modern developer platforms.
Proven success operationalizing cross-functional delivery measurement-bridging product, engineering, and finance.
Background in consulting, technology strategy, or transformation leadership is a plus.

Responsibilities

Define, evolve, and institutionalize the enterprise delivery operating model, integrating Agile, Lean Portfolio Management, and DevOps principles to create scalable, efficient execution patterns.
Serve as the center of excellence for delivery methodologies, partnering with engineering, product, and portfolio leaders to ensure consistent application and maturity.
Develop frameworks and toolkits to standardize portfolio governance, delivery planning, and measurement across teams.
Partner with Developer Experience and Platform teams to define developer productivity and experience metrics aligned with industry benchmarks (e.g., DORA, SPACE frameworks).
Drive continuous learning and maturity improvement through onboarding, playbooks, and targeted enablement programs.
Define and operationalize delivery health and performance metrics (velocity, quality, predictability, capacity utilization, developer experience)
Lead the design and rollout of dashboards and reporting systems that transform delivery data into executive and operational insights.
Partner with Finance and Product to connect delivery performance to business outcomes-improving investment transparency and ROI tracking.
Conduct developer experience research and benchmarking to identify systemic friction points and prioritize improvement investments.
Own the roadmap and governance for delivery tooling ecosystems (e.g., JIRA, ADO, Confluence, analytics platforms).
Drive tooling standardization and adoption, ensuring consistent workflows, data hygiene, and automation across portfolios.
Partner with enterprise architecture and platform engineering to align tooling investments with productivity and operating model goals.
Operate as a trusted advisor to Technology and Product leadership, bringing data-driven insights and pragmatic recommendations.
Lead change management efforts that drive adoption of new practices, tools, and performance systems across the organization.
Foster a culture of transparency, accountability, and continuous improvement.
Communicate insights and recommendations effectively to executives and portfolio leaders, connecting delivery performance to strategic business impact.