Account Executive

The Account Executive owns revenue generation from TLDR's highest-value, most complex accounts. This is a senior, quota-carrying role focused on closing large sponsorship and partnership deals with enterprise companies and agencies. You'll run full-cycle sales end-to-end from account strategy and discovery through pricing, negotiation, close, and expansion. You'll work closely with Sales leadership and cross-functional partners while acting as a trusted advisor to senior marketing and growth leaders. This is not a high-volume SMB role. It's a seat for someone who knows how to sell custom, non-commoditized media solutions into real buying committees.

In this role, you will:

• Own a defined book
• Build and execute account strategies for enterprise brands and agencies
• Lead complex, multi-stakeholder sales cycles from first meeting to close
• Sell premium sponsorships, branded content, and integrated marketing programs
• Manage pricing, packaging, negotiation, and deal structuring
• Forecast accurately and maintain strong pipeline discipline
• Collaborate with Marketing, Ops, AM, and Product to deliver and expand strategic accounts
• Serve as the voice of strategic customers internally, influencing GTM strategy and offerings

Within 6 months, you are:

• Fully ramped on TLDR's product, audience, pricing, and sales motion
• Owning and advancing a healthy pipeline aligned with ramp expectations
• Closing initial strategic deals (new logos and/or expansions)
• Running a repeatable, structured sales process on complex opportunities
• Leveraging AI-powered workflows to reduce manual work and increase selling time
• Viewed internally as a trusted closer on high-impact deals

• 25 years in media, advertising, or agency partnerships
• 5+ years of quota-carrying sales experience selling into accounts with multiple buying groups
• Proven success in B2B media or advertising sales with complex or long sales cycles
• Experience selling sponsorships, branded content, or integrated marketing programs
• Comfortable selling consultative, custom, non-commoditized offerings
• Experience working with senior marketing, growth, or revenue leaders (VP+ / C-suite)
• Strong judgment around deal qualification, pricing, and tradeoffs
• Clear, confident communicator who can run executive-level conversations

• Have only sold transactional SMB deals or high-volume inbound
• Rely entirely on templates, decks, or BDRs to create momentum
• Avoid pricing and negotiation conversations
• Need heavy process or management oversight to move deals forward
• Aren't comfortable operating in a fast-moving, resource-lean environment

Compensation: $185k$350k OTE (60/40 base + incentive split)

Location: 100% remote (US & Canada)

Team Events: Annual company offsite

Time to Recharge: Flexible PTO + holidays

Health Benefits: Medical, dental, and vision (100% paid option)

401(k): Empower 401(k)

Paid Parental Leave: 12 weeks paid leave for birthing and non-birthing parents

Home Office Stipend: MacBook Air M4 + equipment

Learning & Development Stipend

Autonomy and Agency: Real ownership, direct access to leadership, and the ability to shape how TLDR grows its strategic revenue motion

If you're ready to make a real impact at a profitable, fast-growing media company, we'd love to hear from you.