AI GTM Engineer, Tailscale
CA$191.6-239.9k
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
CA$191.6-239.9k
+ Equity
101-200 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- Tailscale is looking for an AI GTM Engineer who thrives on building fast, scrappy solutions that unlock new growth opportunities
- More than mastering any single tool, what matters most is a willingness to experiment, learn, and share what works.
- 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 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.)
What the job involves
- 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
- You'll 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received with reviewers agreeing that it is easy to set up and a great tool for developers. The company plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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