Chief of Staff to Head of GTM

We are building the scheduling infrastructure for the world. If Stripe handles payments, Cal.com handles time.

Our mission is simple: connect a billion people by 2031 by making calendar scheduling effortless and invisible. Just as Stripe powers payments behind the scenes for millions of businesses, Cal.com is becoming the foundational scheduling layer that powers individuals, teams, startups, F1000 companies, FAANG organizations, and governments.

Millions of users already rely on Cal.com every day. We are a stable, profitable, high-growth PLG-first Series A company at ~$9M ARR, with strong fundamentals and a $175M valuation. We move fast but avoid short-lived trends that die in 18 months. We focus on building real, lasting infrastructure that serves our users for the long term.

We are looking for a Chief of Staff to the Head of Go-To-Market.

This person will act as the operational backbone of the GTM organization, ensuring initiatives move from idea to execution without friction.

You will own cross-functional GTM projects, operating cadences, reporting systems, hiring coordination, and the internal infrastructure that allows the GTM team to scale.

You will frequently make decisions on behalf of the Head of GTM, balancing speed, taste judgment, and attention to detail.

Success in this role means GTM initiatives launch faster, communication becomes clearer, and the organization consistently compounds.

• Own the execution of GTM initiatives across Paid, Social, Outbound, Affiliate, Partnerships, and AEO to ensure projects launch on time and hit defined outcomes.
• Run weekly GTM operating rhythms, including planning meetings, action items, follow-through, and cross-functional coordination.
• Build and maintain GTM briefs & dashboards that answer how much are we spending? What return are we getting? Where should we invest the next dollar?
• Serve as the DRI (directly responsible individual) for strategic GTM projects delegated by the Head of GTM.
• Identify bottlenecks slowing down the team and implement systems, automations, or AI workflows to eliminate them.
• Coordinate hiring pipelines, onboarding plans, and documentation for GTM roles.
• Make day-to-day operational decisions on behalf of the GTM organization so momentum is never blocked waiting for executive input.

You are the kind of person who:

• Wants true accountability, real mentorship, and the chance to learn in 6 months what takes most people 6 years
• Wants to understand and implement what the top 1% of operators do  and stay on the cutting edge
• Is looking for a stable, profitable, high-growth company at the exact right stage to be able to say you’ve helped drive growth from ~$10M to $100M ARR
• Prefers building real infrastructure that serves millions of users worldwide over chasing short-lived trends
• Values meaningful equity at a Series A company with a $175M valuation. Equity that can actually matter

• 2–5 years of experience in Chief of Staff, Growth Operations, Revenue Operations, Strategy & Operations, Consulting, Startup Operations, or related roles.
• Demonstrated ability to independently own projects from beginning to end.
• Experience coordinating work across multiple stakeholders and functions.
• Strong written and verbal communication skills.
• Comfort working with dashboards, spreadsheets, and operational reporting.
• Familiarity with modern productivity and AI tools.
• High agency and a bias toward action.

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

A focused, high-trust environment: we work hard between ~9–5, then we cut off and recharge. No 996 hustle culture. We believe sustainable intensity beats burnout.

• 🌐 Work from our office in downtown Manhattan, NYC (hybrid ok)
• 💸 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
• 💻 Macbook and AI subscriptions/tokens as required
• 🧘 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