The PBS Engineering Managing Director, will own the engineering model and technical delivery required to integrate, modernize, and re-implement capability across the broader Express Scripts technology ecosystem so that it operates with New PBM Platform. The role is the senior technical owner for the systems, engineering practices, and client-transition activities that surround New PBM Platform, translating program direction into an engineering strategy, a multi-year roadmap, and a coordinated delivery model. Working across federated technology, product, operations, account management, and business teams, this leader will ensure existing systems are modernized and integrated with New PBM Platform, that work arriving from the Orchestration Hub and the capability build arm can be built, tested, and released by PBS teams, that client waves meet defined readiness criteria, and that services continue without disruption for clients that remain on the legacy platform.

The PBS Engineering Managing Director will establish and lead the PBS Engineering organization, overseeing delivery, integrated planning, integration and end-to-end testing, migration, cutover and contingency, and technical support for business operations. The leader will set the engineering model for the organization, covering code and repository strategy, environments, pipelines, test approach, and release governance across the existing systems, and will partner closely with New PBM Platform platform, product engineering, the Orchestration Hub, and existing PBM technology leaders to align platform growth with enterprise integration and migration requirements, resolve highly complex technical issues with limited precedent, and provide clear, decision-ready recommendations to executive leadership.

Core Responsibilities Include

Engineering Strategy & Executive Alignment

·   Develop and drive the three- to five-year engineering strategy, roadmap, governance model, and delivery approach for New PBM Platform integration, modernization, and client re-implementation.

·   Translate enterprise and executive priorities into clear outcomes, sequencing, investment needs, engineering and organizational capabilities, and execution plans across the PBS engineering organization.

·   Advise executive leadership on strategic direction, major delivery and technical decisions, organizational alignment, risk tradeoffs, and readiness for client migration waves.

·   Synthesize complex technical, operational, financial, and client information into compelling narratives and presentation-ready materials that enable timely decisions and organizational commitment.

·   Represent the organization in senior leadership forums and serve as a primary interface with senior business, technology, and external partner leaders.

Engineering Model, Intake & Technical Operations

·   Define and own the engineering model for the organization, covering code and repository strategy, branching, environments, pipelines, automation, test approach, change control, and release governance across the existing estate.

·   Collaborate to establish the path by which work from the Orchestration Hub and the capability build arm reaches a organization including how scope is received, estimated, scheduled, built, tested, and released.

·   Raise engineering quality and throughput across teams that build today under different models, standards, and tooling, bringing them to a consistent bar without destabilizing in-flight commitments.

·   Own the technical definition of done for organization’s engineering work, including code quality, test coverage, non-functional thresholds, and production readiness.

·   Apply AI-assisted engineering and automation where they measurably improve speed, quality, and repeatability across integration, conversion, testing, and regression work.

Integrated Delivery & Modernization

·   Own the integrated execution of federated workstreams that modernize retained ESI capabilities and build the integrations required for those systems to operate with New PBM Platform.

·   Establish clear delivery commitments, milestones, dependency management, escalation paths, and performance measures across technology teams that retain their functional reporting lines.

·   Partner with the New PBM Platform’s platform organization and the Orchestration Hub to align scope, acceptance criteria, cross-arm dependencies, risks, issues, testing, and release schedules.

·   Ensure modernization and integration work meets functional, performance, security, reliability, and operational-readiness expectations before client deployment.

·   Balance New PBM Platform commitments with business-as-usual requirements so legacy services remain stable throughout the multi-year transition.

Client Re-implementation, Migration & Cutover

·   Lead the technical model for transitioning clients from the legacy environment to New PBM Platform through sequenced implementation waves and a single integrated plan.

·   Oversee configuration, data conversion and reconciliation, migration tooling, integration and end-to-end testing, cutover planning, contingency procedures, go/no-go readiness, command-center execution, and post-launch stabilization.

·   Partner with business readiness, account management, operations, finance, and product teams to establish wave-specific readiness criteria and ensure the technical plan supports client and operational commitments.

·   Drive repeatable migration and conversion capabilities that improve quality, speed, and predictability across successive client waves.

·   Serve as the senior technical authority on whether a wave is ready to proceed, and ensure each transition is executed at the required scale while protecting clients and services that have not yet moved to New PBM Platform.

Technology Performance, Risk & Operations

·   Establish standards, governance, scorecards, and executive reporting for delivery health, capacity, dependencies, readiness, quality, risk, issues, and operational performance.

·   Drive resolution of complex technical incidents and delivery barriers, using data to shape recommendations, escalation decisions, and corrective action.

·   Ensure appropriate technology risk, security, compliance, resilience, and production-readiness controls are embedded across integration and migration activities.

·   Provide oversight for high-priority initiatives and cross-functional work that falls outside established ownership or requires enterprise-level coordination.

·   Maintain accountability for delivery outcomes, operational excellence, financial stewardship, and policy implementation across the organization.

Organization & Talent Leadership

·   Build and lead a scalable engineering organization spanning delivery, integrated planning, integration and end-to-end testing, migration, cutover and contingency, and business operations technical support.

·   Lead through multiple senior leaders and matrixed teams, setting clear accountability while enabling effective execution across federated organizations.

·   Recruit, develop, and retain high-caliber engineering talent; establish a strong leadership bench and adaptable capacity model aligned to the client-wave roadmap.

·   Create a collaborative, transparent, and outcomes-focused culture that moves work forward through ambiguity, enterprise complexity, and competing priorities.

·   Build trusted partnerships across Technology, Product, Operations, Account Management, Finance, HR, Communications, Security, Infrastructure, Data, and external delivery partners.

Critical Leadership Competencies

·   Drives Vision and Purpose: Translates executive strategy into a compelling long-term direction for New PBM Platform integration, modernization, and client transition.

·   Strategic Mindset: Anticipates future needs, connects enterprise priorities, and builds a practical multi-year path from current state to target state.

·   Delivers Results: Creates accountability across complex, federated work and drives measurable outcomes under demanding timelines.

·   Manages Complexity: Integrates contradictory and incomplete information, identifies critical interdependencies, and creates clear paths forward.

·   Decision Quality: Makes sound, timely decisions using technical, business, operational, client, and risk considerations.

·   Balances Stakeholders: Aligns competing priorities across senior leaders, technology organizations, business functions, clients, and partners.

·   Instills Trust: Builds credibility through transparency, follow-through, sound judgment, and clear ownership.

·   Builds Effective Teams: Creates a strong leadership system across direct, indirect, and matrixed teams.

·   Courage: Surfaces difficult issues, challenges assumptions, and escalates risk when required to protect enterprise and client outcomes.

·   Communicates Effectively: Converts complex information into concise, decision-ready communications tailored to executive, technical, business, and client audiences.

·   Manages Ambiguity: Establishes direction and momentum where roles, solutions, or precedents are still emerging.

·   Situational Adaptability: Adjusts leadership approach as the program moves from strategy and mobilization through implementation waves and steady-state operations.

Critical Technology Competencies

·   Demonstrated leadership of large-scale engineering organizations across technology transformation, platform implementation, modernization, systems integration, and enterprise migration programs.

·   Deep understanding of complex application ecosystems, integration patterns, data conversion, testing, release management, production readiness, and operational support.

·   Command of modern engineering practice, including source control and branching strategy, CI/CD pipelines, automated testing, environment and test data management, observability, and change and release control.

·   Experience establishing governance and delivery models across federated technology organizations and matrixed teams.

·   Ability to evaluate architecture, engineering, security, infrastructure, data, resilience, and non-functional requirements, and to make sound technical decisions at enterprise scale.

·   Experience leading client or customer implementations that require coordinated business readiness, technical migration, cutover, contingency, and stabilization.

·   Strong command of Agile, Waterfall, and hybrid delivery approaches, with the judgment to apply fit-for-purpose methods across different systems and workstreams.

·   Familiarity with AI-assisted software delivery and automation, and the judgment to know where it adds real value inside an engineering organization.

·   Demonstrated ability to use delivery, quality, incident, capacity, financial, and operational data to identify trends, manage risk, and guide executive decisions.

·   Proven ability to translate complex concepts into clear roadmaps, executive narratives, operating models, and presentation-ready recommendations.

Qualifications

·   Bachelor's degree or equivalent related experience required; advanced degree preferred.

·   15+ years of progressively responsible experience in technology, engineering, platform delivery, technology strategy, or large-scale transformation, including significant managerial experience.

·   Experience leading sizeable employee and partner populations through multiple layers of senior leaders, including directors, senior managers, principals, or equivalent roles.

·   Proven record of developing and executing medium- to long-term strategies and roadmaps with material organizational, operational, financial, and client impact.

·   Demonstrated experience introducing AI-assisted software development lifecycle (AI-SDLC) practices across engineering teams, including the tooling, quality controls, and ways of working required to realize measurable gains in a regulated delivery environment.

·   Demonstrated success influencing executives and leading outcomes across organizational boundaries without relying solely on direct authority.

·   Strong financial, portfolio, vendor, resource, capacity, risk, and performance-management capabilities.

·   Exceptional written, verbal, listening, and presentation skills, including the ability to absorb disparate information and clearly articulate the issue, recommendation, decision, and action required.

·   Strong executive presence, sound judgment, resilience, and the ability to operate effectively in a highly complex and evolving environment.

Experience in healthcare, pharmacy benefit management, regulated technology, or similarly complex transaction-processing environments preferred.

If you will be working at home occasionally or permanently, the internet connection must be obtained through a cable broadband or fiber optic internet service provider with speeds of at least 10Mbps download/5Mbps upload.

For this position, we anticipate offering an annual salary of 209,600 - 349,300 USD / yearly, depending on relevant factors, including experience and geographic location.

This role is also anticipated to be eligible to participate in an annual bonus and long term incentive plan.

At The Cigna Group, you’ll enjoy a comprehensive range of benefits, with a focus on supporting your whole health. Starting on day one of your employment, you’ll be offered several health-related benefits including medical, vision, dental, and well-being and behavioral health programs. We also offer 401(k), company paid life insurance, tuition reimbursement, a minimum of 18 days of paid time off per year, paid holidays, and leaves of absence. For more details on our employee benefits programs, click here.

About The Cigna Group

Doing something meaningful starts with a simple decision, a commitment to changing lives. At The Cigna Group, we’re dedicated to improving the health and vitality of those we serve. Through our divisions Cigna Healthcare and Evernorth Health Services, we are committed to enhancing the lives of our clients, customers and patients. Join us in driving growth and improving lives.

Qualified applicants will be considered without regard to race, color, age, disability, sex, childbirth (including pregnancy) or related medical conditions including but not limited to lactation, sexual orientation, gender identity or expression, veteran or military status, religion, national origin, ancestry, marital or familial status, genetic information, status with regard to public assistance, citizenship status or any other characteristic protected by applicable equal employment opportunity laws.

If you need a reasonable accommodation to complete the online application process, please email seeyourself@thecignagroup.com for assistance.  Please note that this email inbox is dedicated to accommodation requests only and cannot provide application updates or accept resumes.

The Cigna Group has a tobacco-free policy and reserves the right not to hire tobacco/nicotine users in states where that is legally permissible. Candidates in such states who use tobacco/nicotine will not be considered for employment unless they enter a qualifying smoking cessation program prior to the start of their employment. These states include: Alabama, Alaska, Arizona, Arkansas, Delaware, Florida, Georgia, Hawaii, Idaho, Iowa, Kansas, Maryland, Massachusetts, Michigan, Nebraska, Ohio, Pennsylvania, Texas, Utah, Vermont, and Washington State.

Qualified applicants with criminal histories will be considered for employment in a manner consistent with all federal, state and local ordinances.