Head of GTM Engineering

We’re looking for a Head of GTM Engineering to architect and build the automation infrastructure that powers our go-to-market engine, acting as a force multiplier for our sales and marketing teams. This role combines technical engineering skills with revenue operations logic to build robotsthat handle lead routing, enrichment, AI-driven research, and outbound sequencing.

Who We Are

🏔Product: TLDR is the largest network of tech newsletters in the world, with over 7M subscribers covering everything from startups and software engineering to AI, cybersecurity, product, and more. Every issue is written by builders in tech. Both TLDR Crypto writers both work at Coinbase, TLDR Dev is written by engineers from DeepMind and Meta, TLDR AI is written by researchers from Anthropic and Adobe. That’s why TLDR is the best way to stay current on what truly matters in tech.

💪Team: Our 24-person full time team includes alumni of TikTok, Business Insider, Morning Brew, and other top media brands.

📈Traction: We doubled our revenue from 2024 to 2025 and are looking to double revenue again in 2026. We are supported by advertisers who want to reach tech’s decision makers, including AWS, Google Cloud, Anthropic, Slack, Notion, and GitHub.

About The Role

In this role, you will:

Own the GTM automation architecture. Design, build, and maintain low-code and code-based workflows to connect our GTM systems. Build the Outbound Engine.Develop automated prospecting systems that scrape data, identify leads, and utilize LLMs to research prospects and draft hyper-personalized outreach at scale. Engineer the lead lifecycle. Architect the logic for lead routing and scoring, ensuring every inbound lead is instantly qualified, enriched, and routed to the right rep with zero latency. Deploy internal AI agents. Create AI workflows that assist the sales team by auto-generating account research briefs, summarizing calls, and updating CRM fields automatically. Maintain system hygiene and APIs. act as the technical owner for HubSpot integrations and third-party APIs, ensuring data flows accurately and error logs are resolved immediately.

What Success Looks Like

Within 6 months you will have effectively overhauled our GTM infrastructure including but not limited to:

Fully Automated Inbound Routing: 100% of leads are scored and routed instantly without manual intervention. AI Enrichment Stack: A live system that automatically enriches accounts with non-standard data (hiring trends, news signals) using LLMs. Outbound Efficiency: A scalable programmatic outbound workflow that generates high-quality SQLs for the sales team.

Data Integrity: Reduction of duplicate or garbagedata in the CRM by >90% through automated cleaning protocols.

About You

3+ years of experience in Growth Engineering, GTM Engineering, Technical RevOps, or Backend Engineering with a focus on internal tools. Primary skills: Workflow Automation (n8n, Make, Zapier), Scripting (Python or Javascript/Typescript), API Integration (REST/Webhooks), SQL, AI Engineering (Prompt Engineering, OpenAI API, etc.).

You’re Not a Fit If You…

You’re a pure non-technical admin – we need someone who can write scripts, manipulate JSON, and debug API errors, not just manage user permissions. Don’t enjoy operating in ambiguity or startup environments.

Why You'll Love It

🤑Compensation: $150,000 - 250,000

🌎Location: We’re a 100% remote company distributed across the US and Canada

🤝Team Events: Annual team offsite. Tell us where we should go next!

🏝️Time to Recharge: Flexible PTO. Most team members will enjoy 2-3 weeks off per year + holidays

🏥Health Benefits: Comprehensive medical, dental and vision benefits with 100% paid option

📈401(k) Plan: Empower 401(k)

🍼Paid Parental Leave

💻Home Office Stipend: We're on Macbook Air M4s. Get a new monitor, headset, and chair on us.

🔰Learning & Development Stipend: We are a curious group that believes in learning.

💪Autonomy and Agency: Contribute to the growth of one of the largest newsletters in the world.

📥 If you're ready to make a tremendous impact at a bootstrapped and profitable startup, please apply. Please let us know if you need any accommodation during any part of the interview process.

Press and Publications

Inc story on how TLDR was foundedPricing and demographic information in TLDR’s latest media kit