Executive Assistant

Simile

14h•$200,000 - $250,000

About The Position

Simile is seeking a Senior Executive Assistant to support the COO and GTM leadership as the company’s go-to-market organization scales. The role partners closely with the COO and leaders across sales, marketing, and customer success, helping manage competing priorities and keep a fast-moving, customer-facing organization running smoothly. It includes strategic ownership over how the GTM leadership team operates and is broader than calendar management. The assistant will manage executive communications and priorities, coordinate customer engagements, maintain the GTM leadership operating cadence, organize complex travel and events, partner with cross-functional teams, and build scalable systems and workflows for the COO’s office. The position also includes special projects.

Requirements

Experience as an executive assistant, including direct support of C-suite executives; experience supporting a COO, CRO, or other GTM leader is ideal.
A proven track record supporting several senior leaders at once and balancing competing priorities.
Experience handling confidential information and sound judgment about when to act, escalate, or decline on an executive’s behalf.
Ability to represent executives effectively with enterprise customers, partners, and investors, in writing and in person.
Excellent time management and exceptional attention to detail.
Proactive ownership, including anticipating needs, closing loops, and identifying ways to improve operations.
High proficiency with Google Workspace and Slack, and curiosity about using AI tools to work faster.
Ability to thrive in a fast-paced environment with shifting priorities while maintaining a positive attitude.
Strong interpersonal skills, a collaborative style, and the ability to build trust while leading with empathy and agency.

Nice To Haves

Experience at a high-growth, venture-backed startup, ideally during a period of rapid revenue growth.
Familiarity with enterprise sales motions, forecasting cadences, or CRM tools such as Salesforce or HubSpot.
Experience planning sales kickoffs, executive dinners, customer events, or conference presence.
Experience coordinating board meetings, investor updates, or fundraising logistics.

Responsibilities

Act as the primary partner to the COO, managing their calendar, inbox, and priorities.
Communicate on the COO’s behalf with customers, partners, investors, and candidates with discretion and professionalism.
Coordinate executive customer meetings, onsites, and business reviews with Fortune 100 accounts, ensuring each interaction is well prepared.
Support GTM leadership meetings, pipeline and forecast reviews, and planning cycles by owning agendas, pre-reads, notes, and action-item follow-through.
Plan and manage complex domestic and international travel for multiple executives, including multi-city customer trips, conferences, and last-minute changes.
Plan GTM offsites, sales kickoffs, executive customer dinners, and industry events from concept through execution.
Partner with the CEO’s office, Chief of Staff, revenue operations, marketing, and other executive assistants to align schedules, priorities, and shared initiatives.
Build systems, templates, and workflows to help the COO’s office scale as the GTM team grows.
Take on special projects.