Senior Executive Assistant

At Clover Health, we are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

The Executive Support team plays a critical role in helping Clover's leaders operate at their highest level. As the Senior Executive Assistant supporting our Chief of Staff and SVP of Innovation & Delivery (I&D), you'll serve as a trusted partner who supports the SVP manage competing priorities, builds an effective rhythm of business, and creates the structure needed to lead a growing team responsible for some of Clover’s most mission-critical initiatives. You will combine excellent executive support with strong team operations, helping establish leadership cadences, improve information flow, and maintain momentum across complex, cross-functional work.

As a Senior Executive Assistant, you will:

• Serve as the Executive Assistant to the Chief of Staff and SVP of Innovation & Delivery, owning a complex, evolving calendar and ensuring the executive’s time reflects her most important business priorities.
• Own and continuously improve the SVP’s rhythm of business, including leadership team meetings, one-on-ones, team all-hands, planning sessions, business reviews, and offsites.
• Coordinate internal and external meetings, including preparing agendas, pre-reads, decision logs, action tracking, and communication cadences that ensure stakeholders arrive informed and prepared.
• Manage domestic and international travel, itineraries, expenses, and logistics while troubleshooting issues as they arise, and travel occasionally to support the SVP at key meetings, events, or team gatherings.
• Act as a trusted thought partner by understanding organizational priorities and helping optimize the executive's time and focus.
• Build polished, board- and executive-ready presentations and briefing documents, using AI tools to accelerate first drafts, synthesize research, and summarize meetings.
• Act as an AI-forward thought partner: identify repeatable workflows (correspondence, meeting notes, status reporting) that can be automated or accelerated with AI tools, and implement them.
• Coordinate leadership meetings, onsite visits, and executive events, ensuring a seamless experience for attendees.
• Provide strategic project coordination by tracking priorities, decisions, milestones, and action items and ensuring critical cross-functional initiatives maintain momentum in partnership with the SVP and I&D team.
• Partner closely with leaders across Innovation & Delivery, Office of the CEO, and other business functions to improve communication, organization, and execution.
• Continuously identify and create scalable processes, and modern collaboration tools, including AI, that create efficiencies, improve communication, accountability, and execution across Innovation & Delivery.
• Partner closely with Clover’s broader Executive Support team and provide backup coverage for other executives as needed.
• Handle sensitive information with the highest level of confidentiality and discretion.

Success in this role looks like:

Within your first 90 days, you will:

• Establish a strong partnership with the SVP of Innovation & Delivery and understand key business priorities.
• Created and managed a predictable leadership cadence and I&D team all-hands.
• Create structure and consistency across calendar management, meeting preparation, and executive workflows.
• Build effective relationships with cross-functional stakeholders and become a trusted point of contact.

Within your first 6 months, you will:

• Anticipate executive needs with minimal direction.
• Successfully coordinate recurring leadership meetings and support priority initiatives through effective follow-up and organization.
• Recommend and implement process improvements that increase executive productivity.

Long term, you will:

• Become a trusted strategic partner who enables the SVP to operate efficiently and effectively.
• Help improve organizational effectiveness by creating scalable administrative processes and providing dependable project coordination support.
• Be recognized for your ability to bring order, urgency, and execution to a fast-moving organization.

You should get in touch if:

• You have 5+ years of experience supporting senior executives in a fast-paced, high-growth environment.
• You excel at managing competing priorities while maintaining exceptional attention to detail.
• You're proactive, resourceful, and comfortable anticipating needs before they're communicated.
• You communicate confidently with executives and stakeholders at every level while exercising sound judgment and discretion.
• You're highly organized, adaptable, and energized by supporting leaders who move quickly.
• You are highly proficient with Google Workspace and modern collaboration and project-management tools; you're an active, confident user of AI tools for drafting, research synthesis, and meeting summarization, and you enjoy finding new ways to apply them.
• You can build a clean, executive-ready presentation or briefing doc from a rough set of notes, with strong instincts for structure and story.
• You enjoy keeping projects organized and can comfortably provide light coordination support across multiple initiatives.
• You're motivated by Clover's mission to improve healthcare through technology, innovation, and operational excellence.

Benefits Overview:

• Financial Well-Being: Our commitment to attracting and retaining top talent begins with a competitive base salary and equity opportunities. Additionally, we offer a performance-based bonus program, 401k matching, and regular compensation reviews to recognize and reward exceptional contributions.
• Physical Well-Being: We prioritize the health and well-being of our employees and their families by providing comprehensive medical, dental, and vision coverage. Your health matters to us, and we invest in ensuring you have access to quality healthcare.
• Mental Well-Being: We understand the importance of mental health in fostering productivity and maintaining work-life balance. To support this, we offer initiatives such as No-Meeting Fridays, monthly company holidays, access to mental health resources, and a generous flexible time-off policy. Additionally, we embrace a remote-first culture that supports collaboration and flexibility, allowing our team members to thrive from any location.
• Professional Development: Developing internal talent is a priority for Clover. We offer learning programs, mentorship, professional development funding, and regular performance feedback and reviews.

Additional Perks:

• Employee Stock Purchase Plan (ESPP) offering discounted equity opportunities
• Reimbursement for office setup expenses
• Monthly cell phone & internet stipend
• Remote-first culture, enabling collaboration with global teams
• Paid parental leave for all new parents
• And much more!

About Clover: We are reinventing health insurance by combining the power of data with human empathy to keep our members healthier. We believe the healthcare system is broken, so we've created custom software and analytics to empower our clinical staff to intervene and provide personalized care to the people who need it most.

We always put our members first, and our success as a team is measured by the quality of life of the people we serve. Those who work at Clover are passionate and mission-driven individuals with diverse areas of expertise, working together to solve the most complicated problem in the world: healthcare.

From Clover’s inception, Diversity & Inclusion have always been key to our success. We are an Equal Opportunity Employer and our employees are people with different strengths, experiences, perspectives, opinions, and backgrounds, who share a passion for improving people's lives. Diversity not only includes race and gender identity, but also age, disability status, veteran status, sexual orientation, religion and many other parts of one’s identity. All of our employee’s points of view are key to our success, and inclusion is everyone’s responsibility.