AI GTM Engineer

Tailscale

105d • $143,000 - $179,000

About The Position

Tailscale is looking for an AI GTM Engineer who thrives on building fast, scrappy solutions that unlock new growth opportunities. You’ll use AI tools, LLMs, no-code/low-code platforms, and lightweight automation to accelerate how our GTM teams experiment, operate, and grow. In this role, you’ll be a hands-on partner to Sales, Marketing, and Product, prototyping AI-powered workflows, automating repetitive processes, and stitching together systems that help our teams move faster. More than mastering any single tool, what matters most is a willingness to experiment, learn, and share what works.

Requirements

• 2–3+ years of software engineering experience, ideally full-stack (internships can count as experience)
• Fluency in tools like Clay, Zapier/Make/Tray/N8N, GPT-5, Retool, Notion, Airtable, Python, JavaScript, SQL, LangChain, or similar
• Experience connecting GTM systems (HubSpot, Salesforce, analytics tools, web platforms) into cohesive stacks
• Strong cross-functional collaborator—able to work with Marketing, Product, Data, and RevOps to turn business needs into technical solutions
• Curious and experimental problem-solver who keeps up with emerging AI and automation technologies
• Comfortable designing and troubleshooting APIs, data flows, and automated workflows
• Able to learn new systems quickly and approach traditional GTM problems with novel engineering solutions

Nice To Haves

• Prior experience in B2B SaaS or fintech growth
• Experience working with structured and unstructured data in modern data stacks (React, Next.js, dbt, Looker, etc.)

Responsibilities

• Prototype and launch AI-powered workflows to improve speed, personalization, and targeting across marketing channels (e.g., GPTs for ad copy, AI-driven segmentation, auto-generated landing pages).
• Build and maintain internal tools and automation to scale sales and marketing execution.
• Partner with leads to prioritize and run high-impact growth experiments (e.g., SEO/AEO automation, AI-driven content workflows).
• Automate repetitive GTM processes, from campaign QA to reporting to lead enrichment.
• Use APIs, webhooks, and LLMs to connect systems into smarter, scalable infrastructure.
• Share tools, playbooks, and lightweight agents that empower GTM teams to move faster.
• Partner with Sales and Marketing Leaders to identify workflow pain points and simplify, streamline, or automate them over time.
• Contribute to cross-functional projects that improve GTM process design and reduce manual effort.
• Work closely with Sales, Marketing, and Product to translate business needs into working technical solutions.
• Drive innovation in marketing technology, always looking for ways to improve efficiency and effectiveness.

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity incentive plan, and variable commission.
• Comprehensive group benefits with no waiting period for health, vision, dental, and more.
• Remote first company with options for in-office collaboration depending on team needs.
• Opportunities to connect with other Tailscalars through retreats and off-sites.
• Support for personal and professional development with $1500 USD annually for professional development.
• Flexible paid time off program for any situation life throws your way.
• Build-your-own home office setup with a company-owned laptop and reimbursement for home internet.
• Generous parental leave program from your first day.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Number of Employees: 101-250 employees