<div>About Tailscale  Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. Were building a future for the Internet thats easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, were backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.</div>Job Description 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. Key Responsibilities <ul> <li>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).</li> <li>Build and maintain internal tools and automation to scale sales and marketing execution.</li> <li>Partner with leads to prioritize and run high-impact growth experiments (e.g., SEO/AEO automation, AI-driven content workflows).</li> <li>Automate repetitive GTM processes, from campaign QA to reporting to lead enrichment.</li> <li>Use APIs, webhooks, and LLMs to connect systems into smarter, scalable infrastructure.</li> <li>Share tools, playbooks, and lightweight agents that empower GTM teams to move faster.</li> <li>Partner with Sales and Marketing Leaders to identify workflow pain points and simplify, streamline, or automate them over time.</li> <li>Contribute to cross-functional projects that improve GTM process design and reduce manual effort.</li> <li>Work closely with Sales, Marketing, and Product to translate business needs into working technical solutions.</li> <li>Drive innovation in marketing technology, always looking for ways to improve efficiency and effectiveness.</li> </ul> What We Are Looking For <ul> <li>2–3+ years of software engineering experience, ideally full-stack (internships can count as experience) </li> <li>Fluency in tools like Clay, Zapier/Make/Tray/N8N, GPT-5, Retool, Notion, Airtable, Python, JavaScript, SQL, LangChain, or similar</li> <li>Experience connecting GTM systems (HubSpot, Salesforce, analytics tools, web platforms) into cohesive stacks</li> <li>Strong cross-functional collaborator—able to work with Marketing, Product, Data, and RevOps to turn business needs into technical solutions</li> <li>Curious and experimental problem-solver who keeps up with emerging AI and automation technologies</li> <li>Comfortable designing and troubleshooting APIs, data flows, and automated workflows</li> <li>Able to learn new systems quickly and approach traditional GTM problems with novel engineering solutions</li> <li>(Nice to have) Prior experience in B2B SaaS or fintech growth</li> <li>(Nice to have) Experience working with structured and unstructured data in modern data stacks (React, Next.js, dbt, Looker, etc.)</li> </ul> As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscales compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hires base salary. Individual offers may vary based on experience and skill set.<div><div><div>CAN Pay Ranges</div><div>$191,620—$239,860 CAD</div></div></div><div>Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic! What We Offer <ul> <li>An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.</li> <li>A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).</li> <li>Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!</li> <li>Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.</li> <li>Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. </li> <li>Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. </li> <li>Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! </li> <li>A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. </li> <li>Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. </li> </ul> Please be aware that legitimate emails from Tailscales talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit <a href="https://tailscale.com/scam-awareness">https://tailscale.com/scam-awareness</a>.</div>

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