Chief of Staff to Head of GTM

Cal.com•New York, NY

1d•Hybrid

About The Position

Cal.com is building the scheduling infrastructure for the world, aiming to make calendar scheduling effortless and invisible. They are a stable, profitable, high-growth PLG-first Series A company with approximately $9M ARR and a $175M valuation. The company focuses on building lasting infrastructure. This role will serve as the operational backbone for the Go-To-Market (GTM) organization, ensuring initiatives transition smoothly from concept to execution. The Chief of Staff will manage cross-functional GTM projects, operating cadences, reporting systems, hiring coordination, and the internal infrastructure necessary for the GTM team's growth. This position requires making decisions on behalf of the Head of GTM, prioritizing speed, judgment, and attention to detail. Success will be measured by faster GTM initiative launches, clearer communication, and consistent organizational compounding.

Requirements

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.

Nice To Haves

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

Responsibilities

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.