AI Go-to-Market Engineer

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September 12

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Tailscale

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SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

📋 Description

• Prototype and launch AI-powered workflows to improve speed, personalization, and targeting across marketing channels • Build and maintain internal tools and automation to scale sales and marketing execution • Partner with leads to prioritize and run high-impact growth experiments • 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 to improve efficiency and effectiveness

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

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package including base salary, equity, and variable commission. • Comprehensive group benefits with no waiting period covering health, vision, dental, and more. • Remote first company with virtual and in-person social events and corporate co-working program. • Annual company retreat, team/department off-sites, and individual travel budget for meetups in Canada, the US, or the UK. • $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities. • Flexible, paid time off program. • Company-owned laptop (choice of Mac or PC), monthly home internet reimbursement, and $1000 USD home office customization allowance. • Generous parental leave program with top-ups for up to 26 weeks.