Senior AI GTM Engineer

About the Company

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.

About the Role

Well, we are looking for a Senior AI GTM Engineer (AI Automations) 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.

Responsibilities

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.

Qualifications

5+ years in a technical GTM Operations, Revenue Operations, Sales Operations, or automation engineer role at a SaaS company, supporting GTM Operations - 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.

Pay range and compensation package

Calendly takes a number of factors into consideration when determining an employee’s starting salary, including relevant experience, relevant skills sets, interview performance, location/metropolitan area, and internal pay equity. Base salary is just one component of Calendly’s total rewards package. All full-time (30 hours/week) employees are also eligible for our Quarterly Corporate Bonus program (or Sales incentive), equity awards, and competitive benefits.

Calendly uses the zip code of an employee’s remote work location, or the onsite building location if hybrid, to determine which metropolitan pay range we use. Current geographic zones are as follows:

Tier 1: San Francisco, CA, San Jose, CA, New York City, NYTier 2: Chicago, IL, Austin, TX, Denver, CO, Boston, MA, Washington D.C., Philadelphia, PA, Portland, OR, Seattle, WA, Miami, FL, and all other cities in CA.Tier 3: All other locations not in Tier 1 or Tier 2

Equal Opportunity Statement

We aim to provide an inclusive and equitable candidate experience to everyone who expresses interest in working at Calendly. If you are an individual with a disability and would like to request a reasonable accommodation as part of the application or recruiting process, please contact us at recruiting@calendly.com. Calendly is registered as an employer in many, but not all, states. If you are located in Alaska, Hawaii, California, Montana, North Dakota, South Dakota, Nebraska, Iowa, West Virginia, and Rhode Island, you will not be eligible for employment. Note that all individual roles will specify location eligibility.

All candidates can find our Candidate Privacy Statement here. Candidates residing in California may visit our Notice at Collection for California Candidates here: Notice at Collection.