Senior GTM Engineer

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?

Well, 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?

• 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.
• 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.
• Proven track record integrating workflows across GTM systems and partnering with systems‑admin teams for tools like Salesforce, Outreach, Marketo, Braze, and Gong.
• 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.
• Curiosity about emerging AI technologies, agent frameworks, and GPT development.
• Bonus: Experience in a hybrid PLG/SLG business.
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time