About the role
Who We Are
🏔Product: TLDR’s mission is to increase tech's signal-to-noise ratio.
Today that means the largest network of tech newsletters in the world, with over 8M subscribers covering startups, software engineering, AI, cybersecurity, product, and more. What makes it work is who writes it. Every issue comes from people building in tech, not reporters covering it. Our writers keep their day jobs: two engineers at Coinbase write TLDR Crypto, engineers at DeepMind and Meta write TLDR Dev, researchers at Anthropic and Adobe write TLDR AI, and robotics and datacenter strategy leads at OpenAI and Meta write TLDR Hardware.
If it matters in tech, it's in TLDR. That's what makes TLDR the best place to find what you need to learn.
💪Team: Our 30-person full-time team includes alumni of Stripe, Spotify, TikTok, Amazon, and Google. We've stayed intentionally small, which means every person here owns a function rather than a slice of one.
📈Traction: We're bootstrapped, profitable, and on track for $35M in revenue this year - after hitting $9M in 2024 and $20M in 2025. The advertisers who fund it want tech's decision-makers: AWS, Google Cloud, Anthropic, Slack, Notion, and GitHub.
About the Role
This is an Account Executive role selling into emerging and scaling SaaS companies. We operate an AI-heavy sales model. The grunt work - research, deck-building, pricing, prep - is largely automated. That means your day is spent where it matters: in the deal, with the buyer, using judgment the tools can't replace. We're not looking for someone to run a script. We're looking for someone smart, hungry, and hard to stop.
In this role, you will
- Own a book of accounts end to end - prospect, pitch, negotiate, and close.
- Sell the outcome, not the rate card: connect TLDR placements to the buyer's needs and challenges.
- Use our AI tooling to move faster than any rep could manually - and give us sharp feedback that makes the tools better.
- Keep momentum on deals others would let stall.
- Celebrate your closed won deals for both velocity and increased ACV
What Success Looks Like
Within 6 months you will
- Be fully ramped on TLDR’s product, audience, pricing, and sales motion.
- Own and consistently advance a healthy pipeline aligned with quota expectations.
- Close a steady volume of new business and expansion deals.
- Run a disciplined, repeatable sales process across a high-velocity book of accounts.
- Use AI-powered workflows to increase speed, improve preparation, and spend more time selling.
- Be viewed internally as a reliable closer who creates momentum and delivers consistent results.
About You
- 3-5 years of ad sales experience, ideally selling into a B2B vertical. Newsletter experience is a plus
- A track record of doing hard things and enjoying the process. You keep score, and you like winning
- Business acumen to build a clear, credible case a buyer can take to their own boss, in the language of marketing: attribution, optimization, funnel metrics
- Sharp deal judgment. You read signals, connect dots, and keep deals alive
- AI is already core to how you work, and you pick up new tools fast
You’ll Thrive Here If You…
- Would rather build the playbook than inherit one
- Act on the best available read instead of waiting for the full picture
- Take feedback fast and treat being challenged as useful rather than personal
- Own your deals end to end, with the follow-through and urgency to keep them from stalling
Why You'll Love It
🤑 Compensation: Total cash at target is $200,500 - $390,000
- Base salary: $113,000 to $222,000
- Variable: $75,000 to $148,000 at target, with a 2x uncapped accelerator over goal
- Annual bonus: $12,500 to $20,000 when we hit our company revenue goal, paid in cash each January, with upside up to $25,000 to $40,000 if we beat it
💲How we pay: One of our values is to simplify aggressively, and that includes pay. You get a base, variable pay, and a bonus, all in cash. We place you in the band based on what the interview process shows about your experience. You move up with performance, and we review pay every year. We keep the team small and pay well, so you work alongside strong people. If comp is the only thing stopping you from applying, tell us.
🌎 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