Director of Sales, Startups

Hi! 👋 I'm Val, VP Sales at TLDR.

I'm looking for a Director of Sales, Startups to drive our startup sales engine and scale our startup sponsorship revenue. You'll operate as a player-coach — building, managing, and optimizing a high-velocity sales team focused on turning smaller to mid-sized advertisers into long-term partners.

This role requires deep knowledge of digital media sales, a proven ability to coach reps to exceed quotas, and the analytical mindset to build repeatable systems that scale. You'll partner closely with Marketing, RevOps, and Product to shape our startup sales motion and deliver consistent, predictable revenue.

Who We Are

TLDR is a media company redefining how professionals consume industry news. Our portfolio of 12+ newsletters spans tech, AI, cybersecurity, and more, delivering bite-sized, trusted content to a rapidly growing audience of decision-makers.

We help brands reach their most valuable audiences through sponsorships that deliver performance at scale. We're scaling fast and looking for a Director of Sales, Startups to build and lead our startup sales team, driving efficiency, unlocking new opportunities, and creating a repeatable revenue engine for our startup segment.

🎯 What You'll Do

• Lead TLDR's Startup Sales Team: Own, manage, and coach a team of Startup Sales AEs focused on startup new business acquisition.

• Build Scalable Sales Systems: Design and optimize outbound prospecting, ICP targeting, and sales automation strategies that drive repeatable success.

• Drive Team Performance: Set and enforce performance standards using pipeline data, call scorecards, and CRM hygiene to maximize rep productivity.

• Own Revenue Outcomes: Take accountability for team quotas while rolling up your sleeves as a player-coach with direct account coverage when needed.

• Optimize the Sales Funnel: Create a repeatable startup sales motion from first touch to closed-won, with special focus on top and mid-funnel efficiency.

• Collaborate Across Teams: Partner with Marketing on campaign alignment and RevOps on tooling, dashboards, and process improvements.

• Inform Product Strategy: Provide feedback loops to Product and Partnerships based on advertiser needs, trends, and competitive insights.

🧠 What We're Looking For

• 4+ years of experience in B2B media or digital advertising sales, with at least 1-2 years in a management role

• Proven track record of leading quota-carrying reps to exceed goals through coaching and accountability

• Expert-level proficiency with CRM and sales automation tools (e.g., HubSpot, Apollo, Salesloft)

• Deep understanding of the ad sales funnel, especially at the top and mid-level

• Highly organized, analytical, and comfortable making data-driven decisions at speed

• Strong communicator who can rally teams, unblock reps, and drive cross-functional alignment

• Builder mentality, you love creating playbooks, solving messy problems, and moving fast

• Bonus: Experience scaling startup sales teams in high-growth environments

❤️ Why TLDR

• Leadership role with real impact in a high-growth, metrics-driven media company

• Smart, ambitious, and values-driven team that moves fast and celebrates wins

• Remote-first culture with flexible hours and work-life balance baked in

• Competitive base + performance-based compensation

• 401(k), health, dental, vision, unlimited PTO

• Opportunity to build systems and teams that define our next phase of growth

📥 If this sounds like a fit for you, I'd love to talk about how you can make a big impact at TLDR. Let's build something incredible together!