Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — 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.
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? Well, we are looking for a Senior AI GTM Engineer, AI Agent Builder 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 AI GTM Engineer (AI Automations) at Calendly
On a typical day, you will be working on:
- Prioritizing and managing the GTM automation and experimentation roadmap—working with leadership to align initiatives to revenue, pipeline, and efficiency goals.
- 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 and campaigns 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 strategic priorities and scalable GTM workflow solutions.
- Documenting your work—creating runbooks, guides, and demos to ensure smooth handoffs and QA.
- Analyzing results of experiments at scale and iterating quickly to boost impact.
What do we need from you?
- 6+ years in a technical GTM Operations, Revenue Operations, Sales Operations, or Marketing Operations 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 leading automation projects across GTM systems and partnering with systems 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
The ranges listed above are the expected annual base salary for this role, subject to change.
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 Top Performer 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, NY
- Tier 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
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 let your Recruiter know when first connecting with them. Calendly is registered as an employer in many, but not all, states. If you are located in Alabama, Alaska, Delaware, Hawaii, Idaho, Iowa, Montana, Nebraska, North Dakota, Rhode Island, South Dakota, and West Virginia, 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
This role may require occasional travel for company events, team collaboration, or offsites.
Top Skills
What We Do
At Calendly, we are excited about changing the way the world schedules. We are a profitable company, offering ample opportunities to accelerate your career. We’re obsessed with providing an elegant, delightful experience for our customers. This shapes how we develop, design, market and support. We work hard, move fast and pitch in across departments—and always make time to celebrate our accomplishments.
Join a diverse workforce, leading the way in scheduling automation.
Calendly, a powerful yet simple automated scheduling tool, takes the work out of connecting with others so you can accomplish more. Millions of users benefit from an enjoyable scheduling experience, more time to spend on top priorities and flexibility to accommodate individual users and large teams alike. Calendly works with Google, Office 365 and Outlook calendars and apps like Salesforce, Stripe, PayPal, Google Analytics, GoToMeeting and Zapier for a seamless user experience.
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