Senior Software Engineer, Applied AI

About The Role

TLDR's Applied AI program runs on one thesis: every process at the company should get better automatically as model capabilities improve. An LLM sits in the loop on every workflow, and the work of the people around it shifts from clicking and typing toward writing specs and evals and deciding what good looks like.

In this role, you will:

• Own the build out of new agents, skills, and platform capability for teams across TLDR.
• Build and deploy agents end to end, from design through implementation, evals, and rollout to internal users.
• Write the evals and specs that define what good looks like, so workflow quality is measurable rather than anecdotal.
• Partner with our Applied AI PM on what to build, and make the smaller product calls independently.
• Work directly with stakeholders in sales, revenue ops, editorial, and people ops to find where an LLM belongs in their process.

What Success Looks Like

• Every workflow at the company improves as model capabilities improve.
• Teams write specs and evals and define what good looks like, rather than executing manually, and their processes improve as models improve without anyone rebuilding them.
• Work becomes increasingly push vs pull, by default work is done by LLMs and humans are brought in as needed.

About You

• 5+ years experience including 2+ years building products and systems with LLMs, with at least one agent you took to production and still own.

• You code fluently with AI tools like Claude Code or Codex.

• You write evals as part of building, not after. You can say how you defined good, what you measured, and what you changed as a result.

You'll Thrive Here If…

• You ship end to end and don't wait for someone to spec the small stuff.

• You have product judgment: you can say what you chose not to build, and why.

• You're comfortable in a domain where settled practice doesn't exist yet.

• You can sit with non-engineering stakeholders and find where an LLM belongs in their process.

• The way you build has changed as models have gotten better, and you treat capability improvement as a design input.

• You want surface area across nearly every function of a profitable, bootstrapped company, with no legacy systems to fight, direct CEO access, and an unlimited token budget.

Why You'll Love It

Compensation:

• Base compensation: $250,000 - $300,000

• Annual company performance bonus: $25,000 - $60,000

Location: We're 100% remote across the US and Canada. Work where you want - our bands are set to tier-1 city rates wherever you live.

Team Events: Biannual team offsites. Most recently we've gone to New Orleans, San Diego and Park City!

Time to Recharge: Flexible PTO. Most of the team takes 2–3 weeks a year, plus holidays.

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

401(k) Plan: Empower 401(k)

Paid Parental Leave

Home Office Stipend: Whatever makes you productive - standing desk, second monitor, chair, walking pad.

Learning & Development Stipend: For anything that makes you better at your work, and for AI tools especially. Don't ration your tokens.

If you're ready to make a real dent at a bootstrapped, profitable company, apply. Tell us if you need any accommodation at any point in the process.