Executive Assistant (5+ Yrs Exp)

Executive Assistant to the Founder & CEO (Path to Chief of Staff)

Company: Dysrupt Healthcare
Location: Remote, with proximity to San Juan, Puerto Rico highly preferred
Reports to: Founder & CEO

About Dysrupt Healthcare

At Dysrupt Healthcare, we’re redefining how healthcare works—creating a better experience for employers, employees, and healthcare providers alike.

Our direct-care model is designed to:

· Bring healthcare and employers closer together

· Go deeper with fewer—fewer markets, fewer partners, greater focus

· Continuously improve benefits while lowering costs

We’re breaking away from outdated systems to deliver a healthcare experience that works for everyone. This isn’t just a new brand—it’s a renewed commitment to challenge the status quo and deliver measurable value to those we serve. It’s time to rethink what’s possible in employee health benefits. It’s time to DYSRUPT.

We are building a high-performing, entrepreneurial team and are seeking a highly capable Executive Assistant (EA) to support our Founder & CEO. This role is designed to evolve into a Chief of Staff position as the company scales. Will you join the DYSRUPTION?

Position Summary

The Executive Assistant to the Founder & CEO provides strategic, administrative, and operational support to ensure the CEO’s office functions efficiently and proactively. This role blends traditional executive support with project management, operational leadership, and personal assistance responsibilities.

Initially, the EA will partner closely with an existing Administrative Assistant who manages most email and calendaring for the CEO. Over time, this role will expand into a Chief of Staff function, overseeing a personal assistant and driving execution of company priorities, cross-functional initiatives, and leadership operations.

This position requires sound judgment, strong communication, high discretion, and the ability to anticipate needs in a fast-moving, entrepreneurial environment.

Key ResponsibilitiesExecutive & Strategic Support

· Serve as a trusted partner to the Founder & CEO, acting as an extension of the office.

· Support execution of strategic initiatives and special projects.

· Prepare materials, research, presentations, and briefing documents.

· Track priorities, deadlines, and action items across leadership initiatives.

· Serve as liaison between the CEO and leadership team, staff, partners, and clients.

· Maintain confidentiality on all sensitive and strategic matters.

· Coordinate logistics for board meetings, offsites, leadership meetings, and events.

Operational & Project Management

· Build, improve, and document administrative systems, workflows, and processes.

· Support cross-functional projects on behalf of the CEO.

· Monitor progress against goals and follow up on deliverables.

· Coordinate with vendors and internal teams to ensure smooth operations.

· Assist with internal communications and leadership cadence.

People & HR Support

· Support onboarding and offboarding logistics, including equipment and access.

· Assist with internal operations related to people, culture, and engagement.

· Partner with leadership on team coordination as the company scales.

Partnership with Administrative Assistant

· Work closely with the Administrative Assistant who manages most email and calendaring.

· Create seamless handoffs and workflows between executive support functions.

· Provide coverage and collaboration across scheduling, communications, and priorities.

Personal Assistance (Initial Phase)

· Arrange personal and business travel, itineraries, and logistics.

· Manage personal appointments and scheduling needs.

· Coordinate household vendors and services as needed.

· Purchase gifts and manage special occasions.

· Support select personal projects to free the CEO’s time for strategic work.

Note: As the role evolves into Chief of Staff, personal assistant duties will transition to a dedicated PA under this role’s leadership.

Growth into Chief of Staff

Over time, this role will:

· Oversee a personal assistant.

· Drive execution of company priorities.

· Lead internal operating rhythms.

· Support leadership alignment and decision-making.

· Act as a strategic operator for the CEO and leadership team.

Qualifications & Experience

· Bachelor’s degree or equivalent professional experience required.

· 5+ years supporting senior executives, founders, or leadership teams preferred.

· Experience in healthcare, employee benefits, marketing, or professional services a plus.

· Demonstrated ability to anticipate needs and solve problems proactively.

· Exceptional organizational and project management skills.

· High level of discretion and emotional intelligence.

· Strong written and verbal communication skills.

· Ability to manage competing priorities in a fast-paced environment.

· Proficiency in Microsoft Office (Word, Excel, PowerPoint) and Google Suite (Gmail, Google Drive) and ability to learn new systems quickly.

· Entrepreneurial mindset with intellectual curiosity and strong work ethic.

· Working knowledge of Spanish is a strong asset.

Success Attributes

· Strategic thinker with operational execution ability.

· Calm under pressure and highly detail-oriented.

· Relationship-builder across all levels of the organization.

· Self-starter who thrives with autonomy and accountability.

· Comfortable shifting between tactical tasks and big-picture initiatives.

Disclaimer

This job description outlines the primary responsibilities of the position but is not exhaustive. Duties, responsibilities, and requirements may change at any time with or without notice.

Dysrupt Healthcare is an equal opportunity employer. Employment decisions are based on qualifications, merit, and business needs without regard to any protected status under applicable law.

Job Type: Full-time

Pay: $55,000.00 - $60,000.00 per year

Benefits:

• Dental insurance
• Employee assistance program
• Flexible schedule
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: Remote