Operations Principal & Chief of Staff - Remote

Cigna Healthcare

5d • Remote

About The Position

Reports directly to the President, Allegiance. Operates as a trusted advisor, integrator, and execution partner to the President and Allegiance Executive Leadership Team (ELT). Role Summary The Principal, Business Operations & Chief of Staff serves as the President’s right hand for both management system excellence and enterprise-wide execution. This role blends core Chief of Staff responsibilities with senior operational leadership, ensuring that Allegiance’s leadership team is tightly connected, aligned on priorities, and consistently executing against the business strategy. This role is accountable for designing, running, and continuously improving a strong management operating cadence (planning, reviews, decision forums, and performance management), while also acting as the connective tissue across the executive team to drive collaboration, resolve friction, and accelerate outcomes. The role does not own a traditional function, but delivers impact through influence, orchestration, and disciplined follow-through across leaders. Key Outcomes A clear, repeatable management process that connects strategy, priorities, and performance Strong executive alignment, collaboration, and shared accountability across Allegiance leadership Faster, higher-quality decision-making and execution against business priorities Effective integration of cross-functional initiatives and enterprise dependencies

Requirements

• High School or GED required, Bachelor degree strongly preferred
• 12+ years of experience in business operations, strategy, consulting, Chief of Staff, including 5 + years of direct people leadership experience
• Demonstrated success working directly with senior executives in highly matrixed environments
• Strong business and financial acumen; ability to connect strategy to operating and financial outcomes
• Experience building and running management processes, operating cadences, and performance frameworks
• Healthcare or complex, regulated industry experience 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.

Nice To Haves

• Healthcare or complex, regulated industry experience preferred

Responsibilities

• Chief of Staff & Management Process Leadership Design, implement, and run the Allegiance management operating system, including annual and multi-year planning, goal-setting, KPIs, operating reviews, and executive forums
• Serve as a thought partner to the President on agenda setting, decision framing, prioritization, and follow-up
• Ensure disciplined execution of leadership meetings, operating reviews, and governance forums, with clear decisions, owners, and accountability
• Translate strategic priorities into actionable plans and management rhythms that drive results
• Anticipate issues, risks, and execution gaps and proactively surface options and recommendations
• Business Operations & Performance Execution Partner with Finance, HR, and other enabling functions to ensure alignment between strategy, financial assumptions, workforce plans, and performance outcomes
• Track and monitor progress against Allegiance priorities, identifying risks, tradeoffs, and interdependencies
• Lead or activate cross-business initiatives that require executive-level coordination, particularly in early or ambiguous phases, and transition ownership once stabilized
• Support preparation for enterprise operating reviews and executive updates as needed
• Executive Team Integration & Alignment Act as a unifying force across the Allegiance ELT, ensuring leaders are working collaboratively rather than in silos
• Drive clarity on roles, decision rights, and handoffs across leaders and teams
• Facilitate cross-functional problem solving and resolve friction that impedes execution
• Ensure consistent communication, alignment, and follow-through across leadership
• President Enablement & Enterprise Representation Represent the President and Allegiance in select enterprise forums, initiatives, and operating discussions
• Coordinate key leadership engagements, market visits, and strategic sessions to maximize impact and outcomes
• Serve as a trusted steward of sensitive information, judgment, and executive-level decision-making

Benefits

• 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: Executive
• Education Level: High school or GED
• Number of Employees: 5,001-10,000 employees