Top Chief of Staff Jobs

Serve as strategic partner and operational leader to the President of Rx Marketplace, driving strategy, execution, cross-functional alignment, governance, and high-impact initiatives. Lead planning, executive communications, performance tracking, and organizational design while removing executive roadblocks and supporting leadership development.

The Chief of Staff will support the COO and CEO, drive strategic initiatives, ensure operational alignment, and facilitate decision-making in the fast-paced AI healthcare space.

Serve as strategic partner to the SVP of Product to scale product leadership: run leadership rhythms, own headcount and budget planning, drive AI enablement, curate external product narrative, manage org-health metrics, and resolve cross-functional structural issues to increase decision speed and org effectiveness.

Lead the Chief of Staff function for Legal and Audit Technology: drive strategic planning, budget and workforce management, financial and vendor controls, performance reporting, and cross-team collaboration. Use enterprise-authorized AI to accelerate program planning and risk synthesis while validating outputs and safeguarding data sensitivity. Support talent reviews, resource strategy, and executive communications to align technology initiatives with organizational goals.

Lead and coordinate complex, cross-functional technology programs as a strategic partner to CDAS leadership. Oversee operations, resource allocation, risk and governance, stakeholder communications, and change management. Prepare executive briefings, drive process improvements, and champion adoption of data practices and AI/ML tools to advance organizational objectives.

Lead and deliver medium-to-large cross-functional projects, manage the operational rhythm of the business (meetings, OKRs, reporting), drive internal communications and engagement, identify process improvements, manage risks/issues, and partner with stakeholders to ensure on-time, on-budget delivery.

Serve as strategic advisor and operating partner to Head of Business Development for Cards & Personal Loans. Drive business planning, KPI tracking, executive reporting, governance, and cross-functional coordination. Lead special projects, operating model design, and process improvements to improve organizational effectiveness and enable decision-making and execution across a portfolio of growth initiatives.

Serve as strategic advisor and operating partner to Head of Business Development for Cards and Personal Loans. Drive business planning, KPI tracking, executive reporting, governance routines, cross‑functional coordination, and special projects to advance strategic priorities, improve processes, and enable effective decision‑making and organizational alignment.

Serve as the CEO's right hand to translate founder priorities into clear owners, deadlines, and execution. Lead cross-functional initiatives, run special projects end-to-end, build and maintain internal operating systems and dashboards, own staffing/pod allocation and the company financial model, and ensure follow-through across product, recruiting, finance, and ops.

Partner with the CEO to drive execution across planning, hiring, product, GTM, finance, and culture. Own operating cadence, track leadership priorities, lead cross-functional initiatives, prepare high‑stakes CEO communications, support board/investor and people processes, and build scalable systems to keep the company aligned and accountable.

Serve as Chief of Staff/Project Manager for Model Risk Office, designing and executing budget/headcount processes, strategic planning, leadership meeting cycles, stakeholder engagement, talent management, and special projects. Provide organizational leverage to senior leaders, manage cross-functional coordination, and drive execution of high-visibility priorities to improve operational effectiveness across a 200+ associate organization.

Serve as Chief of Staff to the CHRO, managing the People leadership operating cadence, leading cross-functional initiatives end-to-end, crafting executive communications, resolving issues proactively, and representing CHRO priorities across the organization.

Serve as strategic partner to the New England Market CEO, driving market priorities, performance management, cross-functional alignment, executive decision-support, large-scale initiatives, external partnerships, and governance to improve care delivery across Massachusetts and Connecticut.

Partner with the SVP, Global Value Engineering to drive strategic roadmap execution, lead high-impact cross-functional projects, manage governance and meeting preparation, support budgeting with FP&A, and communicate key initiatives across the organization to enable operational excellence and scale.

Owner of company-wide operational outcomes: run and verify long-lived AI agents to move measurable metrics (first: hiring candidate-to-decision latency), build operating cadence, run back-office/finance/vendor operations, design an ownership program, and grow a human-workforce platform. You model complex systems, instrument processes, write clear specs, and ship operational products inside the company AI brain (Cortex).

Serve as Chief of Staff for the MUOS program, driving operating rhythm, coordinating cross-functional teams, planning and facilitating program reviews and events, tracking actions and program execution, preparing executive briefings, and interfacing with executive offices and customers to ensure program alignment and gated-process compliance.

Serve as strategic partner to CEO/COO to translate strategy into action, drive cross-functional coordination, manage high-priority initiatives, prepare board materials, support executive decision-making, and during ramp-up act as Chief People Officer to shape culture and HR strategy.

Serve as strategic partner to the Enterprise GM to design and execute multi-year strategies and operating models. Lead cross-functional initiatives, align executive priorities and resource allocation, drive organizational change and operational excellence, synthesize insights for senior decision-making, and build relationships across VP+ leaders to mobilize company-level transformation.

Serve as a strategic surrogate to the Chief Strategy Officer: represent the CSO in meetings, craft executive communications and presentations, drive cross-functional strategy initiatives, monitor progress and alignment, collaborate with engineering/product/sales, and articulate the Strategy org's impact internally and externally. Requires technical fluency, strong analytics, and executive presence to accelerate high-impact projects and customer engagements.

Serve as chief of staff to the SVP for U.S. and Canadian payment markets, translating strategy into execution. Lead cross-functional programs, manage and sequence multiple projects, apply quantitative and qualitative analysis to solve ambiguous problems, drive executive communications, and improve business performance across product, technology, finance, and operations.

Serve as a trusted executive partner to an AI R&D organization, driving strategy, stakeholder alignment, program delivery, financial and labor planning, organizational change, and associate engagement while enabling operational excellence.

Serve as Chief of Staff to the Head of Commercial Engineering, driving execution of strategic priorities across Engineering, Product, Finance and legal. Produce executive communications, coordinate cross-functional alignment, translate operational data into recommendations, lead internal communications and employee engagement, and own complex ambiguous problems to deliver actionable outcomes while representing leadership in governance forums.

Serve as strategic partner and Chief of Staff to the Head of Commercial Engineering, driving execution of priorities across Engineering, Product, Finance and legal. Produce executive communications and governance materials, align product and technical teams, translate operational data into recommendations, lead internal communications and engagement, resolve cross-functional dependencies, and represent the Head in governance forums.

Serve as a strategic partner to the CEO and executive team to design and run company planning cycles, drive cross-functional programs, optimize core business processes, build CEO Office operations, and deliver executive-level analysis, dashboards, and board/investor materials to improve operational efficiency and accountability.

Serve as a strategic partner to leadership to develop and implement short- and long-term programs, manage prioritization and roadmaps, identify dependencies, influence cross-functional stakeholders, drive organizational change and operational excellence, create executive-ready presentations, and lead people and complex, sensitive initiatives with limited direction.