New York, New York, United States · Hybrid
About Cal.com 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 effortles…
Skills: Operational Execution, Cross-functional Coordination, Strategic Planning, Reporting & Dashboards, Hiring Coordination
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Act as the operational backbone for the GTM organization, managing cross-functional projects and operating cadences. Responsible for building reporting systems, coordinating hiring, and making operational decisions to ensure GTM initiatives launch efficiently.
Requires 2-5 years of experience in Chief of Staff, RevOps, or Strategy & Operations roles. Candidates must demonstrate high agency, a bias toward action, and the ability to independently own projects from inception to completion.
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.
You are the kind of person who:
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.
Modern, fully customizable scheduling platform
Cal.com is a modern, fully customizable scheduling platform built for teams that care about both power and design. From simple one-to-one meetings to complex, multi-step booking flows, Cal.com gives you complete control over how scheduling works, without sacrificing speed, reliability, or aesthetics. Customize availability, routing, workflows, and integrations to match your exact needs. Whether you’re scheduling sales calls, customer onboarding, interviews, or internal meetings, Cal.com adapts to your processes instead of forcing you into a rigid system. Designed with privacy, performance, and flexibility at its core, Cal.com fits seamlessly into modern teams and products. Use it out of the box, white-label it entirely, or integrate it deeply into your existing stack. Scheduling should feel effortless, intuitive, and considered. Cal.com makes it that way.
Offices: San Francisco, California, US
Modern, fully customizable scheduling platform
Cal.com is a modern, fully customizable scheduling platform built for teams that care about both power and design. From simple one-to-one meetings to complex, multi-step booking flows, Cal.com gives you complete control over how scheduling works, without sacrificing speed, reliability, or aesthetics. Customize availability, routing, workflows, and integrations to match your exact needs. Whether you’re scheduling sales calls, customer onboarding, interviews, or internal meetings, Cal.com adapts to your processes instead of forcing you into a rigid system. Designed with privacy, performance, and flexibility at its core, Cal.com fits seamlessly into modern teams and products. Use it out of the box, white-label it entirely, or integrate it deeply into your existing stack. Scheduling should feel effortless, intuitive, and considered. Cal.com makes it that way.
Offices: San Francisco, California, US
