Account Executive

Tldr; Ottawa; Hybrid; CAD 257,000 - 486,000; Full time

Job summary

TLDR is seeking an Account Executive to sell into emerging and scaling SaaS companies using our AI-heavy sales model. The role focuses on deals where research, pricing, and prep are largely automated, so you can spend time where it matters: with the buyer. You will own a book of accounts end-to-end, negotiate, close, and drive expansion while harnessing AI tools. The position is 100% remote across the US and Canada, offering a competitive OTE and bonus structure.

Qualifications

• 3–5 years of ad-sales experience.
• Ability to present a clear, credible case to buyers.
• 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 and momentum maintenance.
• Resourcefulness in ambiguity.
• Comfort speaking the language of marketing - attribution, optimization, funnel metrics.
• Nice-to-haves: Newsletter / B2B vertical experience.

Responsibilities

• 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.

Skills

Ad sales

AI tools familiarity

Business acumen

Deal judgment

Resourcefulness

Account management

Tools

AI tooling suite

Job description

Who We Are

Product: TLDR exists to increase tech's signal-to-noise ratio. Where we're going: to be tech's intellectual Schelling point - where the future starts its day.

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 29-person full-time team includes alumni of TikTok, Reddit, Amazon, Business Insider, Asana, Morning Brew, and Pinterest. 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

• 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 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.

Press and Publications

• Inc story on how TLDR was founded

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