Executive Assistant to the Head of GTM

About the Role

We’re hiring an Executive Assistant to the Head of GTM to act as a force multiplier across sales, marketing, hiring, operations, and strategic execution at Cal.com.

This is not a traditional assistant role. This is a high agency operator role for someone who wants proximity to company building, GTM strategy, and fast execution inside a scaling startup.

You’ll help drive momentum across the entire revenue organization by reducing operational drag, managing priorities, tightening communication loops, and ensuring the Head of GTM can stay focused on the highest leverage work.

The ideal candidate is intensely organized, calm under pressure, fast moving, and obsessed with follow through. You should treat ambiguity as solvable and operate with strong judgment across both tactical and strategic tasks.

This role is remote and requires exceptional written communication, discretion, and self direction.

What You’ll Do

Own operational execution across GTM

Manage scheduling, coordination, inboxes, travel, and follow ups for the Head of GTM

Track priorities across sales, marketing, recruiting, partnerships, and leadership initiatives

Ensure tasks, projects, and conversations never fall through the cracks

Build systems that improve visibility, accountability, and execution speed

Increase leverage across the revenue org

Prepare concise briefs, summaries, notes, and action items from meetings

Coordinate hiring pipelines, interviews, and candidate communication

Assist with outbound campaigns, events, partnerships, and internal GTM projects

Help organize content calendars, launches, and cross functional initiatives

Move fast and prioritize correctly

Handle urgent requests quickly with strong judgment and minimal oversight

Know when speed matters more than perfection and vice versa

Return decision ready outputs instead of raw information

Reduce noise and operational overhead wherever possible

Act with agency

Anticipate needs before they become problems

Push projects forward through ambiguity and blockers

Research solutions independently and follow through relentlessly

Operate like an owner, not a task taker

Use AI intentionally

Use AI tools to accelerate research, writing, organization, and execution

Maintain thoughtful, human communication in all outputs

Improve workflows through automation and systems thinking

What We’re Looking For

Core traits (non negotiable)

Reliability: you close loops and follow through consistently

Speed: you move quickly without sacrificing judgment

Agency: you find paths forward instead of waiting for instruction

Organization: you create clarity in fast moving environments

Communication: concise, thoughtful, high signal written communication

Experience & skills

Experience supporting a founder, executive, or GTM leader in a startup environment

Strong systems for task management and prioritization

Comfortable operating independently in a remote async culture

High attention to detail and operational rigor

Strong intuition for people, priorities, and momentum

Bonus (Very Nice to Have)

Experience in SaaS, startups, sales, or marketing environments

Familiarity with tools like Slack, HubSpot, Linear, Google Workspace

Experience coordinating recruiting or GTM initiatives

Strong taste in communication, design, or internet culture

Experience using AI tools thoughtfully in day to day work

Why This Role Is Different

This role sits close to decision making, execution, and company growth.

You’ll work directly with the Head of GTM across:

Sales

Marketing

Recruiting

Partnerships

Operations

Content

Strategic initiatives

If you’re ambitious, highly capable, and looking for an accelerated path into operating, growth, or leadership inside startups, this role can compound very quickly.

Compensation

$60k base salary + bonus + equity

Why work at Cal.com?

We’re building Cal.com not just as a product, but as a place to do great work and live a good life.

💸 Earn the same salary no matter where you live

📅 No standups, no micromanagement, no unnecessary calls

🪩 Real flexibility, take time for life stuff, no approval needed

💻 Work in your own flow, pajamas welcome

🧘 30 paid OOO days per year (wherever you are in the world)

✈️ Yearly team retreats in beautiful locations

🏡 People-first culture, stable, family-friendly, kind