Executive Assistant

The federal government spends over $700 billion a year hiring private companies to do critical work, from staffing veterans’ hospitals to maintaining military bases to supporting federal logistics and IT. Many of those contracts legally require employers to set aside money for employee benefits, earned hour by hour. Today most of that is managed through spreadsheets, disconnected vendors, and compliance rules that are nearly impossible to navigate — so employers overspend and risk audits, and workers end up with benefits they can't use or never fully access.

CVRD is the modern tech that fixes it: employers track benefit dollars in real time, stay compliant, and manage healthcare and retirement in one place, while workers finally get benefits they understand. 

This is not a calendar-only EA seat. It's a hybrid of executive support, office management, operations, project coordination, and general problem-solving. You'll work closely with our CEO and Chief Client Officer while supporting the broader team on whatever needs attention that week. One hour you might be preparing leadership for an investor meeting. The next you might be onboarding a new hire, coordinating travel, managing a vendor, planning an offsite, or solving whatever unexpected issue showed up that morning.

We're looking for someone who naturally takes ownership. The person who thrives here is ten steps ahead: you spot the loose ends and soon-to-be-fires and handle them before anyone has to ask. You're resourceful, you take work end-to-end without leaving threads dangling, and no task is beneath you. Most of our team is remote, so the few of us in the office show up for each other, and you genuinely love being the in-person operational anchor that makes that work. 

• Executive support — manage a fluid CEO calendar across investors, customers, and leadership; prepare daily briefs and meeting prep; manage inbox flow and draft outbound comms; run meetings end-to-end with notes and follow-up.
• Travel & events — coordinate travel for leadership, visitors, and conferences (flights, hotels, itineraries, real-time changes); run quarterly workshops, Board meetings, offsites, and company events end-to-end.
• Office & vendor management — keep the Miami office organized, stocked, and visitor-ready; manage office vendors, deliveries, and supplies; act as point of contact for brokers, recruiters, insurance, and operational vendors; partner with finance to keep office, travel, and event spend on budget.
• Cross-functional projects — build and maintain SOPs and internal documentation; support process-improvement, compliance, and communications rollouts; own the projects that don't clearly sit within one department.

Must-haves

• 2+ years as an EA or in operations at a startup or fast-growing company
• A proactive mindset — you surface things before they become problems and take tasks end-to-end
• A real team-player mentality — no task is beneath you, and you enjoy supporting the people around you
• Strong written communication, with tone that adapts across Slack, email, and executive comms
• Extremely organized, with strong judgment and discretion handling sensitive information
• Calm under shifting priorities in a fast-moving environment
• Comfort working independently and figuring things out without constant direction
• Miami-based and excited to work primarily from the office

Bonus Points

• Experience supporting founders or executives at startups
• Experience in healthcare, insurance, benefits, or government contracting
• Familiarity with tools such as Google Workspace, Slack, Gusto, Ramp, Navan, Salesforce, Jira, ClickUp, or similar platforms
• Experience planning events, offsites, conferences, or executive travel

• You notice things other people miss.
• You do not wait to be told what to do. You are resourceful, direct, organized, and comfortable moving between big-picture context and hands-on execution.
• You take ownership of outcomes, not just tasks.
• You follow through.
• You enjoy helping people.
• You are comfortable shifting between strategic work and hands-on work throughout the day.
• You care about details without losing sight of the bigger picture.
• You genuinely enjoy creating order out of chaos.

This is a high-context seat at a fast-moving company. You will work closely with the CEO and senior leadership, which means you will see how a company gets built in real time: the strategy, the deals, the investor conversations, the hard calls, the team decisions, and the operational chaos behind the curtain. There is almost no red tape here. If you see something that should change, you can usually help change it. You will own real, important projects end-to-end, from an offsite to an SOP overhaul to a hiring rollout, and build a rare skill set across executive support, operations, people coordination, office management, events, and communications.

This is a great role for someone who wants more than a traditional EA seat. You will work with smart people, support a mission that matters, and learn directly from a CEO who genuinely wants you to grow.

We're an early-stage, venture-backed company building the operating system for the people side of government contracting. We move quickly, care deeply about the workers our customers employ, and hold ourselves to a high standard. 

We're building something ambitious, and that requires people who are curious, accountable, and excited to solve hard problems. If you enjoy creating order from complexity, improving systems, and helping shape how a company grows, we'd love to hear from you.

CVRD Health is an equal opportunity employer. We hire based on talent, judgment, work ethic, and team fit.