Executive Assistant

Jobtailor; Madison (WI); On-site; USD 100,000 - 150,000; Full time

Job summary

Jobtailor seeks an experienced executive assistant to support a C‑level leader in a fast‑growing tech environment. You will own calendar management, travel planning, and confidential communications, ensuring seamless coordination across leadership functions.

The role requires exceptional organizational skills, polished written and verbal communication, and strong presentation abilities using Google Slides. Collaboration with multiple teams is essential to align on priorities and messaging.

Qualifications

• 5+ years of experience supporting executives at VP or C‑Suite level in tech/SaaS/healthcare environments.
• Highly organized with ability to balance urgent priorities and manage complex travel.
• Exceptional written and verbal communication; proven corporate comms experience.
• Proficiency in building cohesive, professional slide decks (Google Slides).
• Strong business acumen and understanding of organizational goals and metrics.
• Technical savvy with Google Workspace, Slack, Salesforce, and PM tools.

Responsibilities

• Manage a complex, evolving calendar, prioritizing requests against business outcomes.
• Coordinate travel itineraries, corporate bookings, and expense reporting with high accuracy.
• Build cross‑team partnerships to enable leadership collaboration.
• Plan, prepare, and execute leadership meeting agendas.
• Draft and distribute executive updates, memos, and announcements.
• Create compelling slide decks for All‑Hands and stakeholder meetings.
• Attend leadership meetings and translate strategy into actionable updates.
• Plan operational meetings and set agendas with clear outcomes.
• Lead ad‑hoc operational initiatives with cross‑functional milestones.
• Act as gatekeeper and proxy for urgent requests.

Skills

Executive support

Calendar management

Travel logistics

Communication

Presentation design

Cross-team collaboration

Discretion & professionalism

Tools

Google Workspace

Slack

Salesforce

Project management tools

Job description

Responsibilities

• Manage a complex, constantly evolving calendar, prioritizing requests against immediate and long‑term business outcomes while anticipating conflicts before they arise.
• Coordinate friction‑free travel itineraries, corporate bookings, and comprehensive expense reporting with high accuracy.
• Build seamless partnerships across internal teams to facilitate seamless collaboration across leadership offices.
• Orchestrate the planning, preparation, and execution of several leadership meeting agendas.
• Write, refine, and distribute the executive's weekly extended leadership updates, monthly team‑wide memos, and critical organization announcements, ensuring alignment with organizational tone and strategic objectives.
• Partner directly with the executive to conceptualize, storyboard, and design compelling slide decks for All‑Hands meetings, stakeholder syncs, and large‑scale internal presentations.
• Attend leadership meetings to take high‑level strategy and translate it into clear, actionable updates for broader corporate distribution.
• Orchestrate the planning, logistical footprint, and agenda setting for critical operational meetings (weekly leadership, monthly syncs, quarterly planning sessions).
• Lead and execute ad‑hoc operational initiatives from conception to completion, tracking cross‑functional milestones and ensuring accountability across various teams.
• Act as a critical gatekeeper and proxy when appropriate, ensuring urgent requests are triaged and prioritized correctly.

Requirements

• 5+ years of experience supporting executives (VP or C‑Suite level) within a fast‑growing technology, SaaS, or healthcare environment.
• Highly organized: The ability to balance multiple competing, urgent priorities without letting anything drop. Experience managing complex travel and logistics.
• Communication Mastery: Exceptional written and verbal communication skills, with a proven track record of writing corporate comms and translating complex strategies into accessible employee messaging.
• Presentation Portfolio: High proficiency in presentation design (Google Slides) with the ability to visually build a cohesive story arc and create clean, professional visual designs.
• Business Acumen: Strong understanding of corporate structures, organizational goals, and operational metrics.
• Technical Savvy: Expert navigation of enterprise toolsets (Google Workspace, Slack, Salesforce, and modern project management software).
• Sovereign Execution: Absolute discretion handling highly confidential information, paired with high emotional intelligence and low ego.
• Strategic Relationship Management: Ability to navigate complex organizational dynamics with emotional intelligence and diplomacy.