Senior Software Engineer, Applied AI

Who We Are

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. Writers include engineers from DeepMind and Meta (TLDR Dev) and researchers from Anthropic and Adobe (TLDR AI).

Our 24-person full time team includes alumni of TikTok, Reddit, Business Insider, and other top media brands. We doubled our revenue from 2024 to 2025 and are looking to double revenue again in 2026. Supported by AWS, Google Cloud, Anthropic, Slack, Notion, and GitHub.

About the Role

In this role, you will:

• Build Claude Skills and internal AI tooling: Design and implement modular Claude Skills that connect to our core systems (HubSpot, Google Drive, Slack, Sponsy). Create clean abstractions that let non-technical users compose these primitives into useful workflows without writing code.
• Ship autonomous AI agents: Use workflow automation platforms to build agents that operate independently across sales, marketing, and operations — handling research, data enrichment, proposal generation, and routine decision-making without human intervention.
• Own the AI development environment: Establish and maintain the infrastructure that lets the team build with AI tools — whether that's Claude Code, Cursor, or whatever emerges next. Create templates, patterns, and documentation that accelerate everyone's ability to ship.
• Design for composability: Think deeply about interface design between AI components. Build systems where outputs from one tool become inputs to another, where complex capabilities emerge from simple, well-designed primitives.

What Success Looks Like

Within 6 months you will have built:

• A Skills Library That Ships: A catalog of production Claude Skills covering core workflows — CRM analysis, proposal generation, knowledge base search, competitive research — with clear documentation and examples.
• Non-Technical Users Building Things: Marketing, sales, and ops teammates regularly creating their own AI workflows by combining your primitives, without filing engineering tickets.
• Autonomous Agents in Production: Multiple agents running daily that handle tasks previously requiring human attention — lead enrichment, content research, data hygiene, reporting.
• A Reproducible Development Environment: Any team member can spin up Claude Code or equivalent tooling and start building within an hour, with patterns and templates ready to go.

About You

• You've built AI agents that run in production — not demos, but systems that operate autonomously, handle edge cases, and know when to escalate. You understand prompt engineering, context management, and structured outputs at a practical level.
• You code fluently with AI tools like Claude Code or Cursor and modern LLM APIs.
• You have strong product instincts. You build backwards from user needs, and you've shipped internal tools that non-technical teammates actually enjoy using.
• You think in composable systems — small, well-designed pieces that combine into powerful capabilities.
• You ship fast and iterate in the open.

You're Not a Fit If You…

• Haven't used AI-assisted coding tools extensively in your own work.
• Prefer building for technical users only. Half this job is making AI capabilities accessible to people who don't write code.
• Don't enjoy operating in ambiguity or startup environments.

Benefits

• Flexible PTO (2-3 weeks typical)
• Comprehensive medical, dental, vision (100% paid option)
• 401(k) via Empower
• Paid parental leave
• Home office stipend (MacBook Pros, monitor, headset, chair)
• Learning & Development Stipend
• Annual team offsite
• Bootstrapped and profitable