About the Role

The Go-to-Market Engineer owns TLDR's GTM systems end-to-end: the input and interface layer where our team interacts with the revenue stack. This is a building role, not just maintenance - you'll decide what's worth quick-fixing, automating, or re-architecting, and bring an AI-first lens to problems RevOps teams have historically solved by hand. The role sits inside Applied AI, giving you real autonomy over a revenue-critical domain and a seat close to how TLDR builds AI into its GTM systems, work that directly supports our ~$35M FY26 revenue target.

In this role, you will:

• Own GTM systems end-to-end: HubSpot administration, attribution, quota updates, new-product launches, quarter-over-quarter transitions, and CSAT plumbing.

• Own data integrity: build pipelines right and keep fields accurate and flowing downstream.

• Diagnose recurring problems, decide whether to quick-fix, automate, or re-architect, and build the fix.

• Evaluate net-new systems (e.g., Sponsy alternatives) and recommend a path forward.

• Bring an AI-first lens to classic RevOps problems like attribution, and partner with the Head of Applied AI on the broader AI × GTM operating model.
  

What Success Looks Like

In your first 6 months:

• You're the single accountable owner of the GTM systems ring, with the contractor-held work transitioned to you.

• You've built the data-integrity layer - dashboards on field completeness and pipeline health, with alerting on top so no one checks by hand.

• You've shipped your first wave of automations and agent workflows, each with monitoring attached.

• You've documented it - fix-it procedures good enough that a break doesn't require you.
  

About You

• Main background: 4–6 years owning GTM systems at a B2B SaaS or B2B tech company - ideally from an early-stage (Series B–C) environment where you ran GTM systems end-to-end as a single owner

• Primary skills: HubSpot ownership beyond admin; strong critical thinking and consultant-style communication; a product mindset for solution design balanced with pragmatic urgency; root-cause diagnosis paired with quick, clear proposals; hands-on data-integrity ownership (pipeline monitoring, field population, accuracy).

• Secondary skills: Fluency in what AI-first GTM systems look like, applying AI to problems like attribution; familiarity with how APIs and integrations work.

• Nice-to-haves: SQL
  

You’ll Thrive Here If You…

• Want full ownership of a revenue-critical domain, with real autonomy and accountability, not just a task list.

• Are comfortable operating without a paved playbook, this role has more ambiguity than structure.

• Want to sit inside an Applied AI/engineering-focused team rather than a traditional RevOps team, and help define what GTM systems look like in an AI-native org.
  

Why You'll Love It

🤑Compensation: $175,000 - $205,000 + annual company performance bonus

🌎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 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 founded

• Pricing and demographic information in TLDR’s latest media kit