Chief of Staff - Technology (CTO Office)

Role Overview

The Chief of Staff (CoS) for the CTO is a critical leadership role, acting as a trusted advisor to the CTO and a key enabler of the technology organization s success. This individual will ensure efficient communication, alignment, and coordination across the technology leadership team while driving strategic initiatives and operational excellence of the Technology Senior Leadership Team. The CoS will be pivotal in supporting the CTO in organizing leadership meetings, planning offsites, and ensuring the CTO s vision is effectively communicated and executed across the organization. The CoS, capacity allowing, will contribute to delivering strategic initiatives.

Key Responsibilities 1. Strategic Advisory and Communications

- Act as a thought partner to the CTO, providing insights and recommendations to support decision-making.
- Draft, edit, and review high-quality communications on behalf of the CTO, including presentations, emails, and reports.
- Ensure clarity and consistency in the messaging of key priorities, aligning with the overall organizational strategy.
- Facilitate communication and alignment between the CTO and other senior leaders, acting as a bridge where needed.

2. Leadership Meeting Management

- Plan and manage leadership team meetings, including agenda setting, material preparation, facilitation, and follow-up on action items.
- Ensure that meetings are outcome-driven and aligned with strategic priorities.
- Regularly assess the effectiveness of meetings and refine processes to optimize time and productivity.

3. Planning and Coordination of Offsites

- Lead the organization of leadership offsites, including content planning, logistics, and execution.
- Work with the CTO and leadership team to develop offsite agendas that focus on alignment, innovation, and team-building.
- Ensure offsites deliver tangible outcomes and action plans.

4. Program and Project Management

- Oversee strategic initiatives and key projects, ensuring they are delivered on time and meet quality expectations.
- Proactively identify and resolve bottlenecks or risks that may impact program success.
- Track and report on progress toward organizational and technology goals, ensuring accountability across teams.

5. Operational Excellence

- Establish and maintain operational processes that improve efficiency and clarity in the CTO s organization.
- Develop and manage a rhythm of business activities, including MOR, quarterly reviews, performance tracking, and cross-departmental collaborations.

- Facilitate progress report update process with Tech SLT using Tech SLT program tracking tools (ex: JIRA)

6. Relationship Building and Stakeholder Engagement

- Build strong relationships across the organization, including with engineering, product, and other business functions, to facilitate collaboration and alignment.
- Represent the CTO s office in meetings and engagements when the CTO is unavailable.
- Foster a culture of transparency, inclusion, and trust within the technology team.

Key Skills and Experience Essential

- Proven experience in a Chief of Staff, strategic operations, program and project management or similar role within a technology-driven organization.
- Exceptional organizational skills, with the ability to manage multiple priorities and projects simultaneously.
- Strong written and verbal communication skills, with the ability to convey complex information clearly and effectively.
- Experience planning and executing leadership meetings, workshops, and offsites.
- Demonstrated ability to build relationships and influence across senior leadership teams.
- Analytical mindset, with the ability to synthesize data and insights into actionable recommendations.

Preferred

- Experience in program or project management within a technology or engineering environment.
- Familiarity with technology concepts and organizational structures (e.g., Agile, DevOps, product-driven development).
- MBA or equivalent experience in business operations or strategy is a plus.

Key Attributes

- **Strategic Thinker**: Ability to see the big picture while managing details.
- **Proactive Problem Solver**: Anticipates challenges and drives solutions.
- **Collaborative Leader**: Builds trust and fosters collaboration across diverse teams.
- **Adaptable and Resilient**: Thrives in a fast-paced, dynamic environment.

About The Cigna Group

Cigna Healthcare, a division of The Cigna Group, is an advocate for better health through every stage of life. We guide our customers through the health care system, empowering them with the information and insight they need to make the best choices for improving their health and vitality. Join us in driving growth and improving lives.