Account Executive
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AI Summary
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 29-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
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
Drive and competitiveness - a track record of doing hard things and enjoying the process.
Fluency with AI tools and a fast learning curve on new ones.
Business acumen and the ability to present a clear, credible case to a buyer.
Sharp deal judgment - reading signals and connecting dots to keep deals alive.
Resourcefulness in ambiguity.
Comfort speaking the language of marketing - attribution, optimization, funnel metrics.
Nice-to-haves:
Newsletter / B2B vertical experience
You’re Not a Fit If You…
Haven’t worked in the media, advertising, or sponsorship space.
Need a detailed playbook before you can act.
Wait for perfect information instead of making a smart next move.
Get defensive when challenged or struggle to apply feedback quickly.
Treat AI as optional rather than a core part of how you work.
Let deals stall because follow-through, urgency, or ownership slips.
Why You'll Love It
🤑Compensation: $185,000 - $350,000 OTE (60/40 base/incentive split) + annual company performance bonus
🌎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 the latest Macbook Airs or your preferred PC. 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.
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