Executive Assistant

Executive Assistant & Operations Coordinator We are seeking a ruthlessly organized, highly experienced, and deeply proactive Executive Assistant & Operations Coordinator to serve as the strategic right hand to our CEO. This is not a traditional, calendar-only EA desk. This is a high-impact, hybrid role that is part executive support, part office management, part team administration, and part cross-functional operations. We need an operator who is permanently glued to the day-to-day rhythm of leadershipsomeone who naturally anticipates rather than reacts. You are the type of professional who is consistently ten steps ahead, spotting loose ends and putting out fires before anyone else even notices the smoke. You take absolute ownership of outcomes, leave zero threads dangling, and possess the low-ego mindset where no task is too big or too small. The federal government spends over $700 billion a year hiring private companies to do critical workfrom staffing healthcare facilities and maintaining military bases to supporting 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 fragmented spreadsheets, disconnected legacy vendors, and compliance rules that are nearly impossible to navigate. Employers routinely overspend and risk catastrophic audits, while workers end up with benefits they can't use. We are building the modern financial, benefits, and compliance software infrastructure for this massive market. Our platform helps employers track benefit dollars in real-time, maintain legal compliance, and manage healthcare and retirement in a single, unified place, ensuring workers finally get benefits they understand and can access. What You'll Do Executive Support: Manage a highly fluid CEO calendar across investors, high-value customers, and internal leadership. Prepare daily briefs, manage inbox flow, draft executive communications, and run key meetings end-to-end (including agenda setting, minutes, and tracking action items). Travel & Event Logistics: Coordinate end-to-end travel logistics (flights, hotels, complex itineraries, real-time adjustments) for leadership, board members, and visiting partners. Own the execution of quarterly workshops, Board meetings, team offsites, and company events. Office & Vendor Management: Serve as the face of our Miami headquarters. Keep the office pristine, organized, stocked, and client-ready. Act as the primary point of contact for property brokers, recruiters, insurance partners, and operational vendors while partnering with finance to keep spend on budget. Cross-Functional Projects: Build and maintain standard operating procedures (SOPs) and internal documentation. Own specialized, cross-departmental projects that don't clearly sit within a single team (e.g., local onboarding rollouts, workspace compliance, and internal communication initiatives). What You Bring Must-Haves 2+ years of experience as an Executive Assistant, Operations Coordinator, or Office Manager within a fast-growing startup or highly rigorous environment. A Proactive Engine: You fundamentally operate by looking forward. You surface friction points before they become active problems and drive tasks end-to-end without constant oversight. Exceptional Communication: Flawless written and verbal communication skills, with a professional tone that seamlessly adapts across Slack, investor emails, and formal corporate communication. Ironclad Discretion: Highly organized with immaculate judgment, emotional intelligence, and absolute discretion when handling sensitive financial, legal, or personnel information. Miami-Based Presence: A strong desire to work primarily from our Miami office, acting as the culture carrier and administrative anchor for local and visiting teammates. Composure: Calm, steady, and solution-oriented under shifting priorities in a high-velocity, early-stage environment. Bonus Points Prior experience directly supporting founders, C-suite executives, or partners in tech, venture capital, or tier-one professional services. Familiarity with modern operational tech stacks (e.g., Google Workspace, Slack, Gusto, Ramp, Navan, Salesforce, Jira, ClickUp). Background or exposure to high-compliance industries such as healthcare, insurance, fintech, or government contracting. The Kind of Person Who Thrives Here You notice the details other people miss. You do not wait to be told what to do or wait around for a checklist; you are resourceful, direct, and comfortable moving between big-picture context and hands-on execution. You genuinely enjoy creating order out of chaos, following through on every promise, and building the structural scaffolding that allows everyone around you to perform at their absolute best. Why This Role is Compelling This is a high-context, front-row seat at a venture-backed company scaling rapidly. You will work side-by-side with the CEO and senior leadership, giving you an unusual view into how a tech company gets built in real-timethe strategy, the venture rounds, the enterprise deals, and the hard operational calls. There is zero red tape here. You will build a rare, highly versatile skill set across executive operations, people coordination, event production, and corporate communications, learning directly from a leadership team genuinely invested in your professional growth.