US Employer Technology, Chief of Strategy & Operations (CSO)- Managing Director- Cigna Healthcare

The Cigna Group • Bloomfield, CT

3d

About The Position

Summary: The Chief of Strategy and Operations (CSO) is a senior leadership role within the USE Technology organization, serving as a strategic advisor to the USE CIO, and reporting to the Vice President Sales, Underwriting, Client and Chief Operating Officer. This role drives the development and execution of the USE Technology strategy, establishes the operating model, aligns portfolio investments to business priorities, and oversees performance and financial management. This leader ensures strategy-to-execution alignment, organizational effectiveness, and delivery of measurable business outcomes.

Requirements

• 10+ years of progressive leadership experience in technology, strategy, or operations within large, complex organizations- preferably in healthcare.
• Proven ability to translate business strategy into actionable technology roadmaps.
• Exceptional communication and influencing skills, with demonstrated success engaging senior executives and matrixed teams.
• Deep understanding of health plan business (Sales, Underwriting, Product, Operations, Provider etc.).
• Bachelor’s degree required; MBA or advanced degree preferred.

Responsibilities

• Strategy Development and Alignment
• Develop the USE Technology Strategy roadmap and associated sub-strategies (such as Platform modernization, global delivery model etc.) in line with broader business strategy to reflect evolving business priorities and market trends.
• Lead the technology roadmap development in line with strategy and in close collaboration with CIO and senior technology leaders.
• Maintain a deep understanding of USE business, translate business needs into actionable technology priorities and regularly communicate progress to USE CIO and senior business leadership.
• Operating Model and Governance
• Design and implement an operating model to execute on strategy with clear accountability, decision rights, and performance metrics.
• Establish management processes to optimize productivity and throughput across the technology function.
• Represent the CIO in key meetings and ensure effective governance and alignment on critical priorities.
• Partner with matrixed business and enterprise stakeholders to ensure technology governance processes drive efficient, timely, and aligned decision-making.
• Strategy Execution and Portfolio Management
• Manage execution of the strategic roadmap, tracking key deliverables, dependencies, and milestones across the USE Technology portfolio.
• Drive portfolio prioritization, investment alignment and resource allocation collaborating with business partners.
• Serve as the central coordinator to facilitate leadership alignment, informed trade-off decisions, issue resolutions and strategic recalibration.
• Financial Management​
• Oversee financial planning, forecasting, and spend management for the USE technology organization.
• Partner with Finance and portfolio leads to measure ROI and operational efficiency across initiatives
• Leadership, Influence and Organizational Effectiveness
• Serve as a trusted advisor to the CIO, providing objective perspective on what’s working, what’s not, and where to innovate.
• Drive implementation of new ideas and approaches to strengthen performance, mitigate risk, and accelerate delivery.
• Maintain a strong organizational pulse – listen to what people are saying - to identify underlying issues, gaps, and opportunities.
• Partner with HR to enable, manage, and grow talent, building future-ready talent and leadership depth across the technology organization.
• Collaborates with Communications team to support internal communications for U.S. Employer organization.

Benefits

• 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 and paid holidays.

What This Job Offers

• Job Type: Full-time
• Career Level: Director