Account Executive (AI-Powered Ad Sales)

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: Biannual 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.