Executive Assistant

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.

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 escalate, 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
• Note: Final offers are based on experience, specialized skills, interview performance, and relevant training.
• 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.