Job Title: 

Senior Director, Software Engineering   

 

Senior Director, EviCore Software Engineering   

The Senior Director, EviCore Software Engineering & AI Transformation is a strategic technology executive responsible for leading software engineering organizations that deliver scalable, secure, and innovative digital solutions supporting EviCore's business growth and customer experience objectives. This leader drives the modernization of technology platforms, accelerates AI-enabled transformation, and champions organizational change across product, engineering, operations, and business teams. 

 

The role serves as a key technology partner to business leaders, product management, operations, customer experience, and enterprise architecture teams to define and execute a technology vision that advances business strategy, customer outcomes, and operational excellence. The Senior Director will lead large engineering functions, establish modern engineering practices, accelerate adoption of Artificial Intelligence and automation capabilities, and cultivate a high-performing culture focused on innovation, accountability, and continuous improvement. 

 

This leader will play a critical role in transforming how technology is delivered by leveraging AI-powered development, intelligent automation, advanced analytics, and modern software engineering practices to improve speed-to-market, enhance customer experiences, optimize operations, and create sustainable competitive advantage. 

 

Responsibilities 

Technology & Software Engineering Leadership 

• Provide strategic leadership for software engineering teams responsible for the design, development, delivery, and support of enterprise-scale applications and platforms. 

• Establish and execute multi-year technology roadmaps aligned to enterprise strategy, customer needs, and business objectives. 

• Ensure engineering solutions are scalable, secure, resilient, maintainable, and aligned with enterprise architecture standards. 

• Drive adoption of modern software engineering practices including Agile, DevSecOps, CI/CD, cloud-native architecture, observability, and platform engineering. 

• Foster a culture of technical excellence, innovation, accountability, and continuous learning across engineering teams. 

AI Transformation Leadership 

• Define and execute an enterprise AI transformation strategy that embeds Artificial Intelligence, Generative AI, machine learning, and intelligent automation into business and technology processes. 

• Partner with business leaders to identify and prioritize AI use cases that improve customer experience, operational efficiency, productivity, decision-making, and business outcomes. 

• Drive responsible AI adoption, governance, compliance, risk management, and ethical AI practices across the organization. 

• Lead transformation initiatives that leverage AI-enabled software development, automated testing, predictive analytics, intelligent workflows, and digital assistants. 

• Evaluate emerging technologies and establish frameworks for scaling AI capabilities across products, platforms, and operational functions. 

• Champion data-driven decision making through advanced analytics and AI-powered insights. 

Organizational Transformation & Change Leadership 

• Lead large-scale organizational transformation efforts that improve operating models, team effectiveness, delivery predictability, and business agility. 

• Establish a transformation vision that aligns technology investments, organizational structures, talent strategies, and business priorities. 

• Drive cultural change by fostering innovation, collaboration, customer-centricity, continuous improvement, and measurable business value. 

• Develop change management strategies that enable successful adoption of new technologies, operating models, and ways of working. 

• Influence executive stakeholders and matrix partners to build alignment around strategic transformation initiatives. 

Customer Experience and Product Partnership 

• Collaborate with customer experience leaders, product managers, designers, and operational teams to ensure customer needs are reflected in technology strategies and delivery plans. 

• Leverage customer insights, journey mapping, and market intelligence to identify opportunities for digital innovation and experience improvement. 

• Ensure engineering and platform investments directly support enhanced customer, client, provider, and employee experiences. 

• Drive seamless integration of customer experiences across digital channels, platforms, and operational touchpoints. 

Portfolio and Delivery Management 

• Oversee large technology portfolios, balancing strategic initiatives, operational priorities, risk management, and resource allocation. 

• Partner with product and business leaders to prioritize investments that maximize customer impact and business value. 

• Establish metrics, KPIs, and executive reporting to measure engineering effectiveness, customer outcomes, transformation progress, and business results. 

• Remove organizational barriers and enable teams to deliver high-quality solutions efficiently and predictably. 

Talent & People Leadership 

• Build, develop, and retain high-performing engineering and technology leadership teams. 

• Create an inclusive, innovative environment that encourages collaboration, experimentation, and continuous learning. 

• Mentor leaders and emerging talent while establishing succession plans and leadership development programs. 

• Drive workforce transformation by upskilling teams in modern engineering, cloud, data, AI, and automation technologies. 

• Lead geographically distributed and global teams while fostering strong engagement and performance. 

Stakeholder & Executive Management 

• Serve as a trusted advisor to executive leadership, providing strategic recommendations regarding technology investments, AI opportunities, and transformation priorities. 

• Build strong partnerships across technology, operations, customer experience, finance, compliance, security, and business organizations. 

• Present technology strategy, transformation progress, and business outcomes to senior executives and enterprise leadership teams. 

• Collaborate with external partners, vendors, and industry organizations to advance innovation and accelerate deliver.
  

Education & Domain Expertise 

• Bachelor’s degree in computer science, Engineering, Information Technology, or a related field. Master’s degree, MBA, or advanced technical degree preferred. 

• Deep expertise in software engineering, enterprise technology delivery, digital product development, and modern technology architectures. 

• Strong understanding of cloud technologies, platform engineering, Agile delivery methodologies, DevSecOps, application modernization, and enterprise-scale software development practices. 

• Demonstrated experience leading AI, Generative AI, intelligent automation, and digital transformation initiatives that deliver measurable business value. 

• Healthcare, payer, pharmacy benefit management, care management, or regulated industry experience preferred. 

Leadership & Management 

• Proven ability to lead, develop, and inspire high-performing engineering organizations through periods of growth, transformation, and change. 

• Experience managing leaders, managers, engineers, and cross-functional teams in highly matrixed environments. 

• Demonstrated success driving organizational transformation, workforce modernization, and adoption of new technologies and operating models. 

• Ability to establish a clear technology vision, align teams around strategic objectives, and drive execution against enterprise priorities. 

• Strong talent development capabilities, including coaching, succession planning, performance management, and leadership development. 

• Experience building cultures of innovation, accountability, continuous improvement, and customer-centricity. 

Strategic & Analytical Skills 

• Strong strategic planning and execution skills with the ability to align technology investments to business objectives, customer outcomes, and operational efficiency goals. 

• Demonstrated experience evaluating emerging technologies and identifying opportunities to accelerate innovation through AI, automation, analytics, and digital capabilities. 

• Ability to leverage data, customer insights, and market trends to inform technology strategy and investment decisions. 

• Strong financial acumen, including technology portfolio management, budget planning, vendor management, and total cost of ownership analysis. 

• Advanced problem-solving and decision-making capabilities with the ability to navigate ambiguity and complex business challenges. 

• Proven ability to define and execute multi-year technology and transformation roadmaps that support enterprise growth strategies. 

Communication & Collaboration 

• Exceptional communication, presentation, and storytelling skills with the ability to influence stakeholders at all levels of the organization. 

• Proven ability to build strong partnerships across business, product, architecture, operations, customer experience, and technology organizations. 

• Experience leading through influence and coordinating delivery across multiple matrix partners and enabling functions. 
• Strong executive presence with the ability to communicate complex technical concepts to both technical and non-technical audiences. 
• Demonstrated ability to foster collaboration, alignment, and consensus across diverse stakeholder groups to achieve strategic outcomes. 

• Ability to effectively engage executive leadership and drive enterprise-wide decision making. 

Personal Attributes 

• Customer-centric leader with a passion for improving customer, patient, provider, and employee experiences through technology innovation. 

• Transformational mindset with a strong focus on continuous improvement, innovation, and business value realization. 

• Results-oriented leader who balances strategic vision with operational excellence and execution discipline. 

• Adaptable and resilient, with the ability to lead effectively in dynamic and evolving business environments. 

• Continuous learner who stays current on industry trends, AI advancements, technology innovation, and evolving customer expectations. 

• Courageous change agent who challenges conventional thinking and drives organizational transformation. 

• Experience leading geographically distributed teams and fostering a high-performance, inclusive culture. 

• Strong understanding of customer journey management, digital experience strategy, and customer-centric product delivery practices. 

• Proven ability to balance long-term strategic vision with near-term execution and operational excellence. 

• Experience driving adoption of Agile, DevSecOps, cloud, data, AI, and platform modernization capabilities across enterprise organizations. Familiarity with agile delivery processes and practices. 

About Evernorth Health Services 

Evernorth Health Services, a division of The Cigna Group, creates pharmacy, care and benefit solutions to improve health and increase vitality. We relentlessly innovate to make the prediction, prevention and treatment of illness and disease more accessible to millions of people. Join us in driving growth and improving lives. 

 

EviCore Healthcare, a division of Express Scripts, is a nationally recognized leader in medical benefits management, serving over 80 million individuals across commercial, Medicare, and Medicaid plans. Through evidence-based clinical programs, eviCore delivers targeted solutions in diagnostic imaging, oncology, musculoskeletal care, and specialty drug management. Its network of more than 1,000 clinicians, supported by advanced technology platforms, ensures that care is delivered appropriately, efficiently, and cost-effectively—resulting in improved health outcomes and reduced unnecessary utilization. 

 

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.

About Evernorth Health Services

Evernorth Health Services, a division of The Cigna Group, creates pharmacy, care and benefit solutions to improve health and increase vitality. We relentlessly innovate to make the prediction, prevention and treatment of illness and disease more accessible to millions of people. 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.