Calendly

Senior GTM Engineer

United States

Not SpecifiedCompensation
Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
SaaS, BiotechnologyIndustries

About the Team & Opportunity

What’s so great about working on Calendly’s GTM Operations team? GTM Operations at Calendly is a growing team that manages the systems, tools, and processes powering Sales, Marketing, Customer Success, and Customer Experience. We’re leading AI‑driven experimentation and workflow automation to accelerate pipeline, deliver personalized experiences at scale, and eliminate manual work. You’ll join as a key technical partner—driving automation and AI across the entire customer journey alongside passionate GTM leaders.

Why Do We Need You?

We are looking for a Senior GTM Engineer who will bring an experimental, growth‑oriented mindset; deep technical proficiency; and strong partnership & communication skills. You will report to the Senior Director of GTM Operations and be responsible for designing, building, and scaling AI‑driven automation and experimentation that optimizes sales, marketing, and customer success workflows—unlocking new pipeline opportunities, driving revenue, and reducing manual effort.

A Day in the Life of a Senior GTM Engineer at Calendly

On a typical day, you will be working on:

  • Brainstorming and building AI‑powered automations like intelligent lead routing, dynamic visitor campaigns, automated content generation, and voice‑of‑customer feedback pipelines—using OpenAI, Claude, and custom GPT agents.
  • Partnering with Growth Marketing to design and run experiments across outbound and inbound workflows using Clay, Hightouch, and other growth‑tooling platforms (e.g., anonymous visitor tracking, personalization engines).
  • Architecting, building, and maintaining custom API integrations that connect AI services, data sources, and our GTM stack (Salesforce, Outreach, Marketo, Braze, Clay, Hightouch, etc.) to automate end‑to‑end workflows.
  • Building custom LLM/GPT applications to surface insights and streamline GTM workflows.
  • Collaborating with GTM Operations, Sales, Marketing and Customer Success to translate pain points into technical requirements and scalable solutions.
  • Documenting your work—creating runbooks, guides, and demos to ensure smooth handoffs and QA.
  • Analyzing results of AI experiments at scale and iterating quickly to boost impact.

What Do We Need From You?

  • Experience:
    • 5+ years in a technical GTM Operations, Revenue Operations, Sales Operations, or automation engineer role at a SaaS company, supporting Sales, Marketing, or Customer Success teams.
    • Proven track record integrating workflows across GTM systems and partnering with systems‑admin teams for tools like Salesforce, Outreach, Marketo, Braze, and Gong.
  • Technical Skills:
    • Hands‑on experience with AI, automation platforms, and LLMs using Clay, OpenAI (ChatGPT), Anthropic (Claude), Zapier, and Hightouch.
    • Comfortable designing APIs, building webhooks, authoring cloud functions, and querying data in SQL to connect our GTM systems. Familiarity with Python, TypeScript or similar is a plus.
    • Curiosity about emerging AI technologies, agent frameworks, and GPT development.
  • Mindset & Collaboration:
    • A self‑starting, data‑driven mindset with commercial bias and hacker mentality—run experiments, prototype fast, and measure impact.
    • Strong cross‑functional collaboration, documentation, and communication skills—experience managing work in Jira or Asana.
  • Bonus:
    • Experience in a hybrid PLG/SLG business.
  • Work Authorization:
    • Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time.

What’s in it for You?

Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

Our Hiring Process

We aim to provide an i

Skills

AI
Automation
Growth Marketing
API Integrations
LLM
GPT
OpenAI
Claude
Salesforce
Outreach
Marketo
Braze
Clay
Hightouch
Workflow Optimization
Experimentation

Calendly

Automates scheduling for individuals and businesses

About Calendly

Calendly simplifies scheduling for individuals and businesses by providing a platform that automates the process of setting up meetings and appointments. It integrates with popular calendar systems like Google Calendar, Outlook, and iCloud to ensure users can manage their time efficiently and avoid double-booking. Unlike many competitors, Calendly offers a subscription-based model with a free basic version and several premium plans that include advanced features such as team scheduling and custom branding. This tiered pricing approach allows users to start for free and upgrade as they see the value in additional functionalities. The goal of Calendly is to enhance productivity by reducing the back-and-forth communication typically involved in scheduling meetings.

Atlanta, GeorgiaHeadquarters
2013Year Founded
$341MTotal Funding
SERIES_BCompany Stage
Consumer Software, Enterprise SoftwareIndustries
501-1,000Employees

Benefits

Competitive pay
Quarterly bonus
Team member equity
Home office setup
Technology stipend
Pick your own perk stipend
Flexible Time Off
Vacation stipend
Parental leave
Medical, dental, & vision coverage
Fun community events
401k company match

Risks

Increased competition from AI-powered tools like Kalendar.AI threatens Calendly's market share.
Recent 13% workforce reduction may impact innovation and service levels at Calendly.
New CTO appointment could lead to strategic shifts misaligned with customer expectations.

Differentiation

Calendly offers seamless integration with major calendar systems like Google, Outlook, and iCloud.
The platform provides customizable scheduling solutions with features like custom branding and APIs.
Calendly's subscription model includes a free version, encouraging upgrades to premium plans.

Upsides

The rise of hybrid work models increases demand for efficient scheduling solutions like Calendly.
Global scheduling software market projected to grow at 13.1% CAGR from 2023 to 2028.
Increased demand for remote work tools boosts usage of scheduling software by 30% in 2023.

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