AI GTM Engineer

The way organizations buy, sell, and work is changing—and October is building at the forefront of that shift. As our Senior AI GTM Engineer, you’ll help turn emerging AI capabilities into practical, trusted customer experiences, shaping how we explain, demonstrate, and deliver the value of October’s organizational performance platform. This is a new-age, AI-native role for someone who can move fluently between technology, customer needs, and commercial outcomes.

You’ll work closely with Sales and teams across Product, Engineering, and Advisory to make our go-to-market approach smarter and more effective. October brings wellbeing, HR, performance, and behavioral data together so employers can make better decisions and achieve measurable improvements. You’ll help prospects and customers understand that impact through tailored demos, repeatable workflows, and thoughtful use of AI—always with privacy, security, and responsible adoption in view.

• This is a full-time, on-site role with meaningful influence over how a growth-stage company builds its AI-enabled sales motion. You’ll have room to test ideas, learn quickly, and create systems that help the team spend more time understanding customers and less time on repetitive work.

Responsibilities

• Partner with Sales to understand buyer needs and design AI-enabled workflows that improve prospect research, preparation, follow-up, and pipeline execution.
• Build and maintain practical demos, prototypes, and tailored solution narratives that connect October’s platform to each customer’s priorities.
• Develop reusable sales assets, playbooks, and proof points that help the team communicate October’s value consistently across October Health, October People, and October Advisory.
• Work with Product and Engineering to surface customer feedback, validate use cases, and translate sales needs into clear product or tooling opportunities.
• Identify repetitive or high-friction GTM processes, test automation approaches, and measure whether changes improve speed, quality, or customer experience.
• Help establish safe and effective practices for using AI in customer-facing work, including appropriate handling of sensitive information.
• Track adoption and outcomes of the workflows and tools you introduce, then refine them based on team feedback and measurable results.

Requirements

Must-haves

• Significant experience in a customer-facing technical, sales engineering, solutions consulting, revenue operations, or GTM engineering role, ideally in a B2B software environment.
• Hands-on experience using AI tools and automation to build or improve workflows; able to assess where AI adds value and where human judgment is essential.
• Ability to translate complex technical concepts into clear, relevant business outcomes for senior customer stakeholders.
• Strong practical skills with data, integrations, and workflow design, including the ability to troubleshoot and iterate on solutions.
• Excellent communication and collaboration skills, with a track record of partnering across Sales, Product, and Engineering.
• Sound judgment around customer data, privacy, security, and responsible AI use.
• Comfortable working on-site in a fast-moving environment where the role and processes will evolve.

Nice-to-haves

• Experience with HR tech, people analytics, employee wellbeing, or enterprise SaaS.
• Familiarity with CRM systems, APIs, low-code automation, or building internal sales tools and prototypes.
• Competitive compensation aligned with the seniority and scope of the role; specific package details can be discussed during the hiring process.
• The opportunity to shape a new, AI-native role and influence how a growing company brings its products to market.
• Close collaboration with colleagues across Sales, Product, Engineering, and Advisory, with exposure to a broad range of customer challenges.
• Work on a mission focused on healthier organizations and measurable improvements in engagement, retention, and performance.
• A culture that values human-first support, evidence-led decisions, customer partnership, and responsible use of technology.
• On-site collaboration in a fast-moving environment, with expectations and working arrangements discussed during the interview process.

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