Senior Executive Assistant

# Senior Executive Assistant to the CEO

## Company Overview

Confidential U.S. design-tech startup (25+ person team) is a fast-growing landscape architecture company based in Fairfax, Virginia. We pair homeowners across the United States with top-tier landscape architects, designers, and horticulture specialists to create beautiful, sustainable outdoor spaces—completely online. Our platform delivers 2D plans, photo-realistic 3D renders, and contractor referrals in one seamless experience. Backed by thousands of completed projects and national press coverage, we are transforming how people design and build their dream yards.

## About the Role

We are looking for a highly organized and proactive Senior Executive Assistant (EA) to support our Founder & CEO. This remote position is key to keeping our fast-moving leadership agenda on track—managing communications, organizing project information, and providing strategic administrative support. You will work closely with the CEO, design directors, and external partners to streamline day-to-day operations and help turn ideas into action.

This is a long-term, full-time Independent Contractor role reporting directly to the CEO. Preferred working hours are 9 a.m.–5 p.m. US Eastern Time.

## What We Are Searching For

We offer top-of-market pay for the right "A-player." Here's what makes the best Senior Executive Assistants stand out:

**Extensive Experience** – 5+ years supporting C-level leaders (CEOs, founders, VPs) in fast-paced or international environments, handling high-level projects and complex calendars.

**Advanced Skills & Tech Savvy** – Power users of Google Workspace, Microsoft Office, and productivity tools; proficient with video conferencing, CRMs, and no-code/automation tools. Near-native English is required.

**Exceptional Communication & Initiative** – Anticipates needs, drafts responses, represents the CEO with investors and partners, and proactively solves issues before they escalate.

**Reliability & Owner Mindset** – Operates as a true business partner, demonstrates high emotional intelligence and discretion, adapts quickly, manages multiple deadlines, and contributes strategically beyond routine tasks.

## Key Responsibilities

• **Inbox & Calendar Mastery** – Triage and draft replies for the CEO's email, and manage a dynamic calendar of design reviews, investor calls, site visits, and media interviews.

• **Meeting Preparation & Follow-Up** – Prepare agendas, background briefs, and slide decks; capture notes and track action items across design, marketing, and operations teams.

• **Workflow Coordination** – Keep design milestones, 3D render deliveries, and contractor hand-offs on schedule using internal tools and tools like Google Workspace, and Slack.

• **Data & Reporting** – Maintain dashboards on project pipeline, customer satisfaction scores, and contractor performance; compile weekly snapshots for the leadership team.

• **Research & Drafting** – Use AI tools (e.g., ChatGPT, Claude, Gemini) to draft blog posts, press pitches, or investor updates, and to research plants, materials, and sustainability trends for the CEO.

• **Stakeholder Liaison** – Act as point of contact for partner nurseries, software vendors, and media outlets, ensuring questions are answered promptly and accurately.

• **Phone Communication** – Make and receive calls on the CEO's behalf, handle time-sensitive conversations with clients, contractors, and partners, and relay messages accurately.

• **Travel & Event Logistics** – Book conferences, trade-show booths, and site visits; manage travel itineraries and expense reports.

• **Confidential Administrative Support** – Handle sensitive documents, NDAs, and HR paperwork with discretion; assist with occasional personal and family tasks to free up CEO focus.

## Mandatory Criteria

• 5+ years supporting a founder/CEO or senior executive in a tech-enabled or creative services startup.

• Proven expertise in high-volume inbox and calendar management across US time zones.

• Advanced Google Workspace skills and strong spreadsheet know-how (formulas & pivot tables).

• Confident writer with excellent English; able to draft polished communications and reports.

• Outstanding spoken English and professional phone etiquette; comfortable conducting calls with stakeholders on behalf of the CEO.

• Experience coordinating cross-functional projects remotely and tracking deadlines.

• Comfortable using AI productivity tools (ChatGPT, Claude, Gemini, etc.) and eager to learn new software.

• Ability to handle confidential business information and personal matters with absolute discretion.

## Nice-to-Haves

• Background or interest in landscape design, architecture, horticulture, or construction.

• Familiarity with design software (SketchUp, AutoCAD, Lumion) or 3D rendering workflows.

• Experience working with Pipedrive or a similar CRM.

• Prior exposure to contractor or vendor management.

## Ideal Attributes for Success

• **Forward-Thinking** – Anticipates the CEO's needs and prevents roadblocks before they occur.

• **Detail-Obsessed** – Spots inconsistencies in calendars, contracts, or data at a glance.

• **Calm Multitasker** – Juggles shifting priorities and tight timelines without breaking a sweat.

• **Collaborative** – Communicates clearly with designers, engineers, and partners worldwide.

• **Problem Solver** – Finds creative, practical solutions when new challenges arise.

## Remote Work Setup Requirements

• Quiet, dedicated home office with reliable power backup.

• Wired internet connection with minimum 25 Mbps download/upload speeds.

• Noise-cancelling headset and HD webcam for professional video calls.

• Up-to-date antivirus protection and secure password management.

• Dual monitors or ability to efficiently manage multiple windows/applications.

• Reliable smartphone for urgent communications and two-factor authentication.

• Reliable computer capable of running Google Workspace and other productivity applications smoothly without performance issues.

## Compensation Package

This role is for a long-term, full-time Independent Contractor with the following perks:

• **Flexible Remote Work** – Work from anywhere with preferred hours of 9 a.m.–5 p.m. US Eastern Time. We're flexible as long as you maintain ~4 hours of overlap with EST daily.

• **Time Off Benefits** – 12 days of vacation leave annually (after probation) plus 6 days of sick leave per year.

• **Holiday Pay Structure** – Full pay for Philippine regular holidays when not working (double pay if you do work). Special non-working holidays include 30?ditional pay when worked.

• **Health Support** – Monthly health insurance allowance of ?2,500 for you and your family (available after probation period).

• **Work-Life Balance** – Fully remote position with schedule flexibility to accommodate your needs while maintaining effective collaboration with the US team.

## How to Apply

Send your résumé and a short cover letter to ---------- your cover letter, tell us why you're the right person to keep a design-driven startup running smoothly and share one example of a process you improved for a previous executive.

Applications will be reviewed on a rolling basis. We can't wait to meet you!

*Company details will be shared with shortlisted applicants.*