Managing Director

The Cigna Group

. Own the engineering model and technical delivery required to integrate, modernize, and re-implement capabilities across the Express Scripts technology ecosystem for the New PBM Platform .

Posted 10/13/2026full-timeUnited StatesLead💰 $209,600 - $349,300 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in leading large-scale engineering organizations and executing technology transformation strategies, with a strong focus on AI-assisted software development lifecycle practices and operational excellence in regulated environments.

Highest-signal resume keywords

AI-Assisted Software Development Lifecycle (AI-SDLC)Large-Scale Engineering LeadershipGovernance and Delivery ModelsAgile and Waterfall MethodologiesIntegration and Migration Expertise

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Technology StrategyPlatform DeliveryData ConversionRelease ManagementCI/CD PipelinesAutomated TestingChange ControlOperational SupportPerformance ManagementRisk Management

Soft Skills

Exceptional Communication SkillsStrong Executive PresenceResilienceSound JudgmentInfluencing Executives

Tools & Technologies

Source ControlBranching StrategyQuality ControlsObservability ToolsMigration Tooling

Industry Keywords

HealthcarePharmacy Benefit ManagementRegulated TechnologyComplex Transaction-Processing

Tech Stack

Tools & technologies

SDLC

About the role

Key responsibilities & impact

Own the engineering model and technical delivery required to integrate, modernize, and re-implement capabilities across the Express Scripts technology ecosystem for the New PBM Platform
Establish and lead the PBS Engineering organization
Oversee delivery, integrated planning, integration and end-to-end testing, migration, cutover and contingency, and technical support for business operations
Develop and drive a three- to five-year engineering strategy, roadmap, governance model, and delivery approach
Translate enterprise and executive priorities into outcomes, sequencing, investment needs, capabilities, and execution plans
Advise executive leadership on strategic direction, delivery and technical decisions, organizational alignment, risks, and migration-wave readiness
Define code and repository strategy, branching, environments, pipelines, automation, testing, change control, and release governance
Establish intake and delivery processes for work from the Orchestration Hub and capability build arm
Raise engineering quality and throughput across teams and define the technical definition of done
Apply AI-assisted engineering and automation to integration, conversion, testing, and regression work
Own integrated execution of federated workstreams modernizing retained capabilities and building integrations with the New PBM Platform
Establish delivery commitments, milestones, dependency management, escalation paths, and performance measures
Align scope, acceptance criteria, dependencies, risks, testing, and release schedules with platform and orchestration organizations
Ensure functional, performance, security, reliability, and operational-readiness expectations before client deployment
Balance platform commitments with business-as-usual requirements to maintain legacy service stability
Lead technical client transitions through sequenced implementation waves and an integrated plan
Oversee configuration, data conversion and reconciliation, migration tooling, integration and end-to-end testing, cutover, contingency, go/no-go readiness, command-center execution, and post-launch stabilization
Establish wave-specific readiness criteria with business readiness, account management, operations, finance, and product teams
Serve as senior technical authority on migration-wave readiness
Establish governance, scorecards, reporting, and controls for delivery health, capacity, quality, risk, security, compliance, resilience, and operational performance
Drive resolution of complex technical incidents and delivery barriers
Provide oversight for high-priority initiatives requiring enterprise coordination
Maintain accountability for delivery outcomes, operational excellence, financial stewardship, and policy implementation
Build and lead a scalable engineering organization across delivery, testing, migration, cutover, contingency, and technical operations support
Lead through senior leaders and matrixed teams; recruit, develop, and retain engineering talent
Build partnerships across Technology, Product, Operations, Account Management, Finance, HR, Communications, Security, Infrastructure, Data, and external delivery partners

Requirements

What you’ll need

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
Proven record developing and executing medium- to long-term strategies and roadmaps with organizational, operational, financial, and client impact
Experience introducing AI-assisted software development lifecycle (AI-SDLC) practices across engineering teams
Experience with tooling, quality controls, and ways of working for AI-SDLC in a regulated delivery environment
Demonstrated success influencing executives and leading outcomes across organizational boundaries
Strong financial, portfolio, vendor, resource, capacity, risk, and performance-management capabilities
Exceptional written, verbal, listening, and presentation skills
Strong executive presence, sound judgment, resilience, and ability to operate in a complex and evolving environment
Demonstrated leadership of large-scale engineering organizations across technology transformation, platform implementation, modernization, systems integration, and enterprise migration programs
Deep understanding of application ecosystems, integration patterns, data conversion, testing, release management, production readiness, and operational support
Command of source control, 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
Experience leading client or customer implementations involving business readiness, technical migration, cutover, contingency, and stabilization
Strong command of Agile, Waterfall, and hybrid delivery approaches
Familiarity with AI-assisted software delivery and automation
Ability to use delivery, quality, incident, capacity, financial, and operational data to identify trends, manage risk, and guide executive decisions
Ability to translate complex concepts into roadmaps, executive narratives, operating models, and presentation-ready recommendations
Experience in healthcare, pharmacy benefit management, regulated technology, or similarly complex transaction-processing environments preferred

Benefits

Comp & perks

Annual bonus eligibility
Long-term incentive plan eligibility
Medical insurance
Vision insurance
Dental insurance
Well-being and behavioral health programs
401(k)
Company-paid life insurance
Tuition reimbursement
Minimum of 18 days of paid time off per year
Paid holidays
Leaves of absence
Cable broadband or fiber optic internet service requirement for home working (at least 10Mbps download/5Mbps upload)