Chief of Staff to the CEO

About Our ClientThis is a high-impact leadership role serving as the right hand to the CEO within the Business Operations team. This position will act as a force multiplier for the executive team, driving priority initiatives and ensuring organizational alignment as the organization scales its mission to transform prescription medication access and affordability. As Chief of Staff, this individual will be a trusted advisor and strategic partner to the CEO, bridging the gap between vision and execution. About The RoleThe role will manage the CEO's agenda to focus on the highest-priority initiatives, drive cross-functional strategic projects, and provide the analytical rigor needed to make critical business decisions. This role requires someone who thrives in ambiguity, excels at connecting dots across the organization, and is equally comfortable diving into complex data analysis as they are crafting executive communications.This is an exciting opportunity to join a rapidly scaling healthcare technology company that is transforming how Americans access and afford prescription medications. The organization is focused on innovation and growth to expand its services and scale its impact nationwide. The individual will work directly with executive leadership to shape company strategy, drive meaningful impact, and accelerate career growth. This role offers unparalleled exposure to all aspects of running and scaling a high-growth technology company, with the opportunity to transition into broader leadership roles as the company continues to grow.Key ResponsibilitiesStrategic Leadership & ExecutionIn partnership with the CEO and executive team, develop and refine the organization's long-term strategic vision and translate that vision into actionable OKRsSupport the execution of company-wide OKRs through strategic planning, progress tracking, and facilitating trade-off decisions to maintain organizational alignmentAct as a strategic sounding board for the CEO, helping pressure-test ideas and anticipate challenges before they ariseSupport organizational planning processes, including strategic offsites, annual planning cycles, and quarterly business reviewsCEO Support & Agenda ManagementManage the CEO's time and priorities ruthlessly, ensuring focus remains on the company's most critical initiativesAttend key meetings in conjunction with or on behalf of the CEO when appropriate, representing the executive perspective and ensuring follow-through on action itemsPrepare the CEO for important meetings with comprehensive briefing materials, analysis, and strategic recommendationsOperational Excellence & Problem SolvingBuild a deep, end-to-end understanding of how the organization operates within and across functions, as well as how it interacts with customers, its industry, and investorsProvide analytical and operational support to key functions when required (e.g., troubleshooting operational challenges, standing up new capabilities, driving performance improvements)Perform independent analyses for the CEO, President, and other key Executives on critical business questionsLead and operationalize strategic cross-functional initiatives (e.g., profitability optimization, go-to-market strategy, organizational design)Communications & Stakeholder ManagementCreate and refine customer and internal communications, including presentation materials, board decks, strategic updates, and analytical deep-divesEnsure consistent messaging across the organization by coordinating internal communications on behalf of the CEOFacilitate information flow between the CEO and the broader organization, ensuring transparency while protecting confidentiality where appropriateBuild strong relationships across all levels of the organization to foster collaboration and break down silosSpecial Projects & Strategic InitiativesLead high-priority special projects that are critical to the company's success but may not have a natural ownerIdentify opportunities to add value to the CEO and company proactively, bringing solutions rather than just problemsDrive completion of key strategic initiatives, ensuring timely progress and removing barriers to executionRequired QualificationsExperience & BackgroundMinimum of 7 years of experience in strategy, business operations, or related high-impact rolesManagement consulting experience at a top-tier firm is strongly preferredPost-consulting experience in high-growth technology companies, startups, investment banking, corporate development, or strategic operations roles strongly preferredDemonstrated track record of successfully delivering complex initiatives and achieving measurable business impact at scaleExperience in healthcare, digital health, pharmacy, or related industries is a strong plus but not requiredStrategic Thinking & Analytical RigorExceptional analytical and problem-solving skills with the ability to synthesize complex information into clear insights and recommendationsData-driven decision maker who is comfortable with quantitative analysis, financial modeling, and using data to drive strategyExperience defining, implementing, and tracking OKRs or similar goal-setting frameworksAbility to see the big picture while also managing critical detailsOperational ExcellenceSelf-starter who is resourceful, autonomous, and unafraid to roll up your sleeves and tackle ambiguous challengesOutstanding organizational and project management skills with the ability to manage multiple high-priority workstreams simultaneouslyNimble and flexible, thriving in a fast-paced, rapidly evolving environment where priorities can shift quicklyCapable of context-switching multiple times throughout the day while maintaining quality and attention to detailLeadership & Interpersonal SkillsMature, tactful, and highly professional when engaging with very senior stakeholders, both inside and outside the companyExceptional written and verbal communication skills, with the ability to craft compelling narratives for diverse audiencesStrong executive presence and comfort operating at all levels of the organization, from the C-suite to front-line employeesPersonal AttributesHighly curious with a genuine desire to understand the intricacies of the organization's business model and the healthcare industryGoal-oriented with a bias toward action and a strong sense of ownership and accountabilityWilling to invest time upfront to develop deep domain expertise in the enterprise healthcare solution and capabilitiesDiscretion and sound judgment when handling confidential informationPassion for the organization's mission to improve medication access and affordability for patientsWhy Join Us:It is rare to have a company that both deeply impacts its customers and is able to provide its services across a massive population. At this organization, there is a huge impact on people when they are most vulnerable: at the intersection of their healthcare and finances. The organization is also a rapidly growing healthcare company, driving that impact across millions of new patients every year. The business model not only helps people but drives economics that allow for the building of a generational company. It is a relentlessly learning, constantly curious, and aggressively collaborative cross-functional team dedicated to inventing new ways to improve the lives of its customers.Note:“We are not the EOR (Employer of Record) for this position. Our role in this specific opportunity is to connect outstanding candidates with a top-tier employer. Swooped helps candidates around the world to discover and stay focused on the jobs they want until they can complete a full application in the hiring company career page/ATS.”