[Remote] AI GTM Engineer at Tailscale

United States

Tailscale Logo
Not SpecifiedCompensation
N/AExperience Level
N/AJob Type
Not SpecifiedVisa
N/AIndustries

Requirements

  • 2-3+ years of software engineering experience, ideally full-stack
  • 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
  • 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
  • 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, always looking for ways to improve efficiency and effectiveness

Skills

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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