Senior GTM Engineer

Summary

Join Calendly's growing GTM Operations team as a Senior GTM Engineer and be a key technical partner, driving AI-driven automation and experimentation across the entire customer journey. You will design, build, and scale AI-driven automation and experimentation to optimize sales, marketing, and customer success workflows. A typical day involves brainstorming and building AI-powered automations, partnering with Growth Marketing on experiments, architecting API integrations, building custom LLM/GPT applications, collaborating with cross-functional teams, documenting your work, and analyzing experimental results. This role requires 5+ years of experience in a technical GTM Operations role at a SaaS company, hands-on experience with AI and automation platforms, API design skills, and strong collaboration and communication skills. The ideal candidate will possess a self-starting, data-driven mindset and curiosity about emerging AI technologies. Calendly offers a competitive total rewards package including base salary, quarterly corporate bonus program or sales incentive, equity awards, and competitive benefits.

Requirements

• 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

Responsibilities

• Brainstorm and build 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
• Partner 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)
• Architect, build, and maintain 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
• Build custom LLM/GPT applications to surface insights and streamline GTM workflows
• Collaborate with GTM Operations, Sales, Marketing and Customer Success to translate pain points into technical requirements and scalable solutions
• Document your work—creating runbooks, guides, and demos to ensure smooth handoffs and QA
• Analyze results of AI experiments at scale and iterate quickly to boost impact

Preferred Qualifications

Experience in a hybrid PLG/SLG business

Benefits

• Quarterly Corporate Bonus program (or Sales incentive)
• Equity awards
• Competitive benefits