Executive Assistant

JOB DESCRIPTION

POSITION TITLE Executive Assistant to CEO and President & COO

LOCATION On-site/Charleston, SC

HIRING MANAGER CEO

Sunny is changing the world by leveraging digital technologies to help people live healthier lives. Using a digital first strategy, Sunny is helping health plans and employer groups to engage consumers with innovative, integrated health and wealth tools to improve health outcomes and drive quantifiable results.

Our flagship product, Sunny Payments & Benefits, digitally transforms the Medicare Advantage and commercial markets by helping consumers capitalize on their health benefits. We make it easy to spend smarter via directed spend technology for supplemental and specialized benefits. Our companion product, Sunny Rewards, is an integrated Reward Dashboard with a simplified consumer experience designed to maximize rewards. Our intelligent and intuitive tools, together with our seamless integration, deliver success with confidence.

Sunny’s team of experienced leaders is what truly sets them apart. The elite team represents all corners of the market, ensuring a comprehensive and holistic understanding of the dynamics wing from their collective insights, extensive knowledge, and expertise in the field of consumer engagement, the team knows what works and what doesn’t with today’s consumers.

Invaluable lessons learned is the genesis of Sunny, which has led to a fine-tuned product-to-market fit that caters to a range of stakeholders in the healthcare space. Whether it’s payers, employers, or individual consumers, Sunny has refined its solutions to meet their unique requirements. Sunny is unmatched in its ability to customize and employ refreshing levels of creativity, adaptability, and inventiveness.

This is crucial in an industry where trends and demands change rapidly and calls for a very nimble team.

A knowledgeable and diverse management team with a keen understanding of customization and market trends have been brought together to make a significant impact on the way consumers interact with their health and well-being – we hope you consider taking this journey with us!

As the Executive Assistant for Sunny, you’ll be a critical partner to our executive team, helping drive focus, clarity, and momentum across the business. You’ll be based in-person with the CEO and provide remote support to the President and COO. From managing the day-to-day to helping keep big-picture priorities on track, your ability to stay ahead of the curve will make all the difference.

• Provide high-level administrative support to the CEO (in-person) and President & COO (remote).
• Manage complex calendars across multiple time zones; coordinate internal and external meetings, board meetings, investor conversations, and team touchpoints.
• Serve as a communication liaison between the executive team and internal/external stakeholders.
• Prepare briefing documents, meeting agendas, follow-ups, and presentations.
• Coordinate travel logistics, including itineraries, accommodations, and expense reports for the CEO and President & COO.
• Anticipate needs and take initiative to streamline operations and reduce friction for the leadership team.
• Handle confidential information with discretion and professionalism.
• Help facilitate smooth team operations and communications across departments.
• Provide occasional support on ad hoc tasks that align with business priorities.

• Have 4+ years of experience supporting senior executives (startup or high-growth experience is a plus).
• Bachelor of Arts or Bachelor of Science degree.
• Proficient in Microsoft 365 (Outlook, Excel, Word, PowerPoint, Teams).
• Able to quickly learn and adapt to new systems and tools.
• Organized, detail-oriented, and thrive in a fast-paced, ever-evolving environment.
• Proactive problem-solver, who can anticipate needs before they arise.
• Communicate clearly and professionally—both in writing and verbally.
• Are comfortable working across time zones and managing high-volume scheduling.
• Are based locally and can be in the office full-time with the CEO.
• Ability to adjust or move self and light or medium…