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

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