[Remote] AI GTM Engineer at Tailscale

Canada

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Not SpecifiedCompensation

Mid-level (3 to 4 years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, Cybersecurity, NetworkingIndustries

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 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.)

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

Skills

Key technologies and capabilities for this role

LLMsGPTsAPIsWebhooksNo-code platformsLow-code platformsAutomationSEOAEOAI workflowsSales automationMarketing automation

Questions & Answers

Common questions about this position

What experience level is required for the AI GTM Engineer role?

The role requires 2–3+ years of software engineering experience, ideally full-stack, with internships counting toward experience.

What tools and skills should I have for this position?

Fluency is needed in tools like Clay, Zapier/Make/Tray/N8N, GPT-5, Retool, Notion, Airtable, Python, JavaScript, SQL, LangChain, or similar, plus experience connecting GTM systems like HubSpot and Salesforce.

Is this a remote position?

Yes, Tailscale is a fully distributed company, indicating remote work.

What kind of collaboration is expected in this role?

The role involves partnering closely with Sales, Marketing, Product, Data, and RevOps leaders to identify pain points, prioritize experiments, and build solutions.

What makes a strong candidate for this AI GTM Engineer role?

A strong candidate is a curious, experimental problem-solver comfortable with APIs, data flows, and automation, who thrives on building scrappy solutions and keeps up with AI technologies.

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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