Executive Assistant

Simile; United States; On-site; USD 200,000 - 250,000; Full time

Benefits offered by this job

Salary range $200k–$250k USD

Equity available

Health & Wellness benefits

Flexible time off

Job summary

Simile in the United States is seeking a Senior Executive Assistant to the COO & GTM Leadership. You will protect their time, coordinate priorities, and act as a trusted strategic partner across sales, marketing, and customer success.

You’ll own calendars, prepare materials, plan travel, and help scale the GTM organization as revenue grows, while maintaining a high standard of professionalism and discretion.

Qualifications

• Experience as an executive assistant, including direct support of C-suite executives such as a COO, CRO, or GTM leader.
• Proven track record of supporting multiple senior leaders simultaneously with strong judgment.
• Experience handling confidential information with discretion and professionalism.
• Ability to represent executives well with enterprise customers, partners, and investors.

Responsibilities

• Act as the primary partner to the COO. Manage calendar, inbox, and priorities; communicate with customers, partners, investors, and candidates with discretion.
• Coordinate executive customer meetings, onsite visits, and business reviews with Fortune 100 accounts, ensuring thorough preparation.
• Support GTM leadership cadence: staff meetings, pipeline and forecast reviews, planning cycles; own agendas and notes.
• Plan and manage complex domestic and international travel for multiple executives, including multi-city trips.
• Plan GTM offsites, sales kickoffs, dinners, and industry events from concept to execution.
• Work with CEO’s office, Chief of Staff, revenue operations, marketing, and other EAs to align schedules and priorities.
• Build scalable office systems, templates, and workflows to support a growing GTM team.

Skills

Executive support

Multi-executive support

Discretion & judgment

Customer-facing polish

Exceptional organization

Proactive ownership

Tools fluency

Ambiguity tolerance

Empathy & collaboration

Tools

Salesforce

HubSpot

Google Workspace

Slack

Job description

About the Company

Pilots don’t train with real passengers. Actors don’t rehearse with real audiences. Yet, the most consequential decisions in society are often pushed straight to production.

Simile is changing that. We have built the first AI simulation of society, populated by generative agents based on real humans. Our research pioneered the field of AI-based simulation, proving it is possible to model human behavior with high accuracy. Today, we are developing a Foundation Model to predict human behavior in any situation, at any scale.

We have raised $300M in total funding, with a $2B post-money valuation in our latest round. Our investors include Greenoaks, Index Ventures, Hanabi, A*, Bain Capital Ventures, Factory, CVS Health Ventures, and Definition.

About the Role

Simile’s go-to-market engine is scaling fast. Our COO and GTM leaders spend their weeks with Fortune 100 executives, in customer meetings and on the road, while also building the teams, systems, and operating rhythm behind a 5x revenue trajectory. As Senior Executive Assistant to the COO & GTM Leadership, you’ll make sure their time goes to what matters most.

This is not a calendar-only role. You’ll be a trusted strategic partner to the COO and the leaders across sales, marketing, and customer success. You’ll anticipate what’s coming, juggle competing priorities across several executives, and keep a fast-moving, customer-facing organization running smoothly. You’ll have real ownership over how the GTM leadership team operates as we scale.

In this role, you will:

• Executive Partnership: Act as the primary partner to the COO. Manage their calendar, inbox, and priorities, and communicate on their behalf with customers, partners, investors, and candidates with discretion and professionalism.

• Customer-Facing Coordination: Coordinate executive customer meetings, onsites, and business reviews with Fortune 100 accounts. Make sure every interaction is well-prepared and reflects the quality bar of the company.

• Operating Cadence: Support the GTM leadership operating rhythm, including staff meetings, pipeline and forecast reviews, and planning cycles. Own agendas, pre-reads, notes, and follow-through on action items.

• Travel & Logistics: Plan and manage complex domestic and international travel for multiple executives, including multi-city customer trips, conferences, and last‑minute changes.

• Events & Offsites: Plan GTM offsites, sales kickoffs, executive customer dinners, and industry events from concept through execution.

• Cross-Functional Partnership: Work with the CEO’s office, Chief of Staff, revenue operations, marketing, and other EAs to align schedules, priorities, and shared company initiatives.

• Process & Scale: Build the systems, templates, and workflows that let the office of the COO scale as the GTM team grows. Take on special projects.

Requirements

Must Haves

• Relevant Experience: experience as an executive assistant, including direct support of C-suite executives, ideally a COO, CRO, or other GTM leader.

• Multi-Executive Support: A proven track record of supporting several senior leaders at once, with the judgment to balance competing priorities without dropping anything.

• Discretion & Judgment: Experience handling confidential information, and the judgment to know when to act, when to elevate, and when to say no on an executive’s behalf.

• Customer-Facing Polish: You represent your executives well with enterprise customers, partners, and investors, in writing and in person.

• Exceptional Organization: Excellent time management with superb attention to detail. Nothing falls through the cracks.

• Proactive Ownership: You anticipate needs before they’re stated, close loops without being asked, and bring ideas for how things could run better.

• Tools Fluency: High proficiency with Google Workspace and Slack, and curiosity about using AI tools to work faster.

• Comfort with Ambiguity: You thrive in a fast-paced environment where priorities shift quickly, and you keep a positive attitude while doing it.

• Empathy & Collaboration: Strong interpersonal skills and a collaborative style. You build trust across the company and lead with empathy and agency.

Nice to Haves

• Startup Experience: Experience at a high-growth, venture-backed startup, ideally during a period of rapid revenue growth.

• GTM Exposure: Familiarity with enterprise sales motions, forecasting cadences, or CRM tools like Salesforce or HubSpot.

• Event Planning: Experience planning sales kickoffs, executive dinners, customer events, or conference presence.

• Board & Investor Support: Experience coordinating board meetings, investor updates, or fundraising logistics.

Compensation & Benefits

At Simile , we provide competitive compensation packages that include base salary, equity, and comprehensive benefits.

• Salary Range: $200,000 – $250,000 USD

• Equity: Grants are available for eligible roles, subject to board approval.

• Health & Wellness: Comprehensive medical, dental, and vision coverage.

• Time Off: Flexible time off policies to support work-life balance.

Our Process

We prioritize thoughtful conversations and clear examples of past work. Our hiring journey is designed to help both sides align on fit, working style, and expectations.

Reapplication Policy: To ensure a fair and thorough evaluation for all applicants, Simile observes a 90-day waiting period before reconsidering candidates for the same role.

Commitment to Diversity & Inclusion

Equal Opportunity: Simile is an equal opportunity workplace. We welcome applicants of all backgrounds and identities, valuing an environment where everyone can contribute authentically.

Accommodations: If you require support or reasonable accommodations during the application process due to a disability, please let us know. We are happy to assist.