Executive Assistant

CVRD raises $5M Series A led by UpfrontCVRD raises $5M Series A led by UpfrontRead articleContact UsCareersExecutive AssistantMiami, FLHybridFull-timeApply for this roleAbout usThe roleWhat you'll doWhat you bringThe kind of person who thrives hereWhy this role is interestingOur mantraApplyAbout usThe 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. The roleThis 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. What you'll doExecutive 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.What you bringMust-haves2+ years as an EA or in operations at a startup or fast-growing companyA proactive mindset — you surface things before they become problems and take tasks end-to-endA real team-player mentality — no task is beneath you, and you enjoy supporting the people around youStrong written communication, with tone that adapts across Slack, email, and executive commsExtremely organized, with strong judgment and discretion handling sensitive informationCalm under shifting priorities in a fast-moving environmentComfort working independently and figuring things out without constant directionMiami-based and excited to work primarily from the officeBonus PointsExperience supporting founders or executives at startupsExperience in healthcare, insurance, benefits, or government contractingFamiliarity with tools such as Google Workspace, Slack, Gusto, Ramp, Navan, Salesforce, Jira, ClickUp, or similar platformsExperience planning events, offsites, conferences, or...