Senior Executive Assistant

Senior Executive Assistant

Executive Operations Partner

Full-Time Remote (Philippines) | EST Hours | 8:00 AM - 5:00 PM

HealthMerch creates promotional products that help health organizations connect with their communities in ways that actually matter. We work with clinics, hospitals, nonprofits, and community health programs across the country on campaigns that spark conversations, build trust, and drive real public-health impact.

We are growing quickly. As we scale, we are building a global team that holds itself to a high standard. Ownership. Clarity. Follow-through. We move fast, we communicate directly, and we care deeply about the work we do.

We are hiring a Senior Executive Assistant who will work directly with our CEO and COO. This is not a traditional assistant role. This is an opportunity to become a true operational and strategic extension of leadership at a company that is building something real.

This role sits at the center of everything. You will own the CEO and COO's calendars, inboxes, and daily operations. You will prepare leadership for meetings, keep the organization informed and aligned, and ensure that nothing falls through the cracks.

Our CEO is fast-moving, creative, and high-level. He needs someone who anticipates what he needs before he asks and protects him from the operational noise that slows him down.

Our COO is structured, process-oriented, and detail-focused. She needs someone who respects her systems and keeps information flowing cleanly.

You need to flex between both without dropping either. If you have done this before at a high level, you will recognize exactly what we are describing.

This role is not for someone who waits to be told what to do, avoids difficult conversations, or needs constant direction.

• Full inbox management: filtering, prioritizing, drafting, and closing loops
• Manage calendars with intention -- protecting time and eliminating unnecessary noise
• Prepare leadership for calls, meetings, and decisions
• Ensure they always have the right information at the right moment

• Sync with Operations, Sales, Design, Order Entry, and Support teams
• Gather updates, clarify details, and deliver distilled summaries
• Watch meeting recordings and surface only what matters
• Keep information flowing cleanly and consistently across the company

• Review upcoming events, launches, conferences, and major initiatives
• Identify bottlenecks, risks, and missing pieces before they surface
• Provide proactive options, solutions, and next steps
• Keep leadership prepared well in advance

• Help the CEO think strategically about accounts and opportunities
• Maintain follow-through and communication with high-value clients
• Represent leadership on calls when needed

• Manage tasks and priorities inside ClickUp
• Ensure teams know what is needed, when, and by whom
• Support documentation, workflows, and recurring processes
• Coordinate travel, events, and logistics with minimal friction

• Reviewing inboxes and surfacing high-priority items before 8:30 AM
• Preparing leadership for a high-stakes client meeting
• Syncing with Operations or Sales on key updates
• Watching a recorded meeting and summarizing what actually matters
• Protecting deep-work blocks on both calendars
• Attending a call as the CEO's proxy
• Flagging an upcoming deadline and moving it forward
• Ending the day with clear lists, completed follow-ups, and aligned next steps

• Proactive. You anticipate needs before they are spoken.
• Calm under pressure. You bring stability to fast-moving situations.
• An exceptional communicator. Clear, concise, and confident.
• Highly organized. Details, structure, and systems come naturally.
• Autonomous. You make thoughtful decisions without waiting for direction.
• Mature and grounded. You push back respectfully and protect priorities.
• Reliable. Confidentiality, professionalism, and judgment are instinctive.
• Camera-ready. You represent leadership with polish and presence.
• Growth-oriented. You want a role that expands as the company does.

• 3 to 5 or more years supporting founders, CEOs, or senior executives as their primary EA
• Experience simultaneously supporting two executives with different working styles
• Hands-on experience managing inboxes, calendars, and communication flows
• Exposure to operations, project management, or cross-functional coordination
• Confidence in tools like ClickUp, HubSpot, Slack, and Microsoft 365
• Experience in promotional products, marketing, e-commerce, or agency environments (a plus)
• Familiarity with EOS (helpful but not required)

Note: If you have come from a BPO or EA placement platform such as Athena, Wing, or Belay, please tell us about your experience there. We want to understand the model you are coming from and how it differs from direct executive support.

• Clear weekly priorities
• Daily check-ins
• High trust, high accountability
• Transparent, direct communication
• Structured feedback during the first 90 days

We call this the Blue Standards. It is not a list of rules. It is how we show up for each other and for the people we serve. Ownership. Transparency. Follow-through. If those words mean something to you in practice and not just on paper, you will fit here.

You will work closely with teams in the U.S., Philippines, South Africa, and more.

You will help shape systems, workflows, and communication company-wide.

Our products help people access care, stay informed, and stay safe.

Potential future paths include:

• Chief of Staff
• Executive Operations Manager
• Director of Executive Support
• Strategic Projects Lead

You will learn this entire business from the inside out.

If this feels like the place where you will do your best work, we want to meet you.

Apply with your resume and responses to the screening questions. The application is detailed by design. We are not looking for polished answers. We are looking for real ones.

This is a rare opportunity to support a CEO and COO directly, operate at a strategic level, and help scale a mission-driven company that is building healthier, more connected communities across the country.

The HealthMerch Hiring Team