Why Headout?

We’re a rocketship: 9-figure revenue, record growth, and profitable

With $130M in revenue, guests in 100+ cities, and 18 months of profitability, Headout is the fastest-growing marketplace in the travel industry, and we’re just getting started. We've raised $60M+ from top-tier investors and are building a durable company for the long term — because that's what our mission needs and deserves. We’re growing, profitable and nowhere near done.

What we do is important

In an increasingly digital world, there is a desperate need to augment our human experience by getting us to interact with the real world around us and the people in it. At Headout, our mission is to be the easiest, fastest, and most delightful way to head out to a real-life experience — from immersive tours to museums to live events and everything in between.

Why now?

The foundation is strong. The opportunity ahead is even bigger. We’ve hit profitability, built momentum, and proven the model — but there’s so much more to build. If you’re looking to join a company where the trajectory is steep and your impact is real, this is the moment.

Our culture

Reinventing the travel industry isn't easy, but that's the fun part.
We care deeply about ownership, craft, and impact, and we’re here to do the best work of our careers. We won’t pretend like it’s for everyone but if you’re a builder who loves solving tough problems, you’ll feel right at home. 

‍ The Role

At Headout, we’re building the AI layer that powers how our Sales team works. As an AI GTM Engineer, you’ll build intelligent workflows, agents, and internal tools that automate repetitive work, improve decision-making, and help our Business Development teams operate at a much higher leverage.

You’ll work across AI, backend systems, and GTM tooling to build production-ready solutions, from partner research and outreach automation to CRM integrations and workflow orchestration. This is a hands-on builder role where you’ll own problems end-to-end, shipping systems that are used every day and continuously improving them based on real usage and business impact.
You’ll work closely with Sales, Product, and Engineering teams to identify high-impact opportunities, move quickly from idea to implementation, and build reliable AI-native systems that make our GTM engine faster and more effective.

This role is based in Bengaluru. We’re looking for candidates who are local or open to relocating.

What Makes This Role Special?

• Own the AI layer of GTM. Build production-ready AI agents, workflows, and integrations that become a core part of how Headout sells and grows.


• End-to-end ownership. From identifying problems with Sales teams to designing, building, deploying, and iterating on solutions, you’ll own the complete lifecycle.


• Build beyond the CRM. Engineer on top of tools like Salesforce and HubSpot using APIs, AI models, and workflow automation, rather than configuring existing systems.


• Ship with impact. Work in a fast-moving team where the success of what you build is measured by real business outcomes, like time saved, better workflows, and improved sales productivity.


• Operate at the intersection of AI and business. Collaborate directly with GTM teams to solve operational problems using modern AI tooling, backend engineering, and automation.

What Skills & Experience You Need?

• 2 to 5 years of software engineering or applied AI experience, with ownership of production systems used by customers or internal teams.


• Strong proficiency in Python or TypeScript, with experience building backend services, integrations, or automation workflows.


• Experience shipping AI-powered applications or workflows into production, with an understanding of monitoring, reliability, and iteration.


• Hands-on experience integrating with business systems using APIs, webhooks, and OAuth, ideally across platforms like Salesforce, HubSpot, Slack, Gmail, or similar.


• Familiarity with modern AI and automation tooling such as OpenAI, Anthropic, LangChain, LlamaIndex, n8n, Clay, or equivalent technologies.


• Strong problem-solving skills and systems thinking, with the ability to turn ambiguous GTM operational problems into scalable technical solutions.


• High ownership and bias for action, with a track record of taking ideas from concept to production.


• Strong data intuition, with the ability to define success metrics, instrument workflows, and iterate based on real usage.


• Excellent communication and stakeholder management skills, with the ability to work closely with Sales teams to understand problems and build solutions that drive adoption

EEO statement

At Headout, we don’t just accept differences — we celebrate it, we support it, and we thrive on it for the benefit of our employees, our partners, and the community at large. Headout provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age or disability. During the interview process, if you need assistance or an accommodation due to a disability, you may contact the recruiter assigned to your application or email us at [email protected].

Privacy policy

Please note that once you apply for this job profile your personal data will be retained for a period of one (1) year. Headout shall process this data for recruitment purposes only. Once the relevant job profile is filled or once the time period of one (1) year from the date of the job application has passed, whichever is later, Headout shall either delete your data or inform you that it shall keep it in its database for future roles. In compliance with the relevant privacy laws, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that the processing of your personal data be restricted. If you have any concerns or questions about the way Headout handle your data, you can contact our Data Protection Officer for more information.