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Director of Sales, Strategic Accounts

3 weeks ago

Remote, Oregon, United States TLDR Full time

We're hiring a Director of Sales, Strategic Accounts to lead our enterprise revenue strategy, manage a team, and build the engine that powers TLDR's largest partnerships. This is a senior leadership role with wide ownership: building the team, scaling processes, shaping long-term customer strategy, and helping architect the next phase of TLDR's growth.

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 24-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

You will lead, scale, and evolve TLDR's enterprise sales organization.

You'll own revenue outcomes across our most strategic verticals and accounts, manage a team of account executives, and build the operational infrastructure that enables us to double revenue again in 2026. You will set standards, coach high performers, and create the systems that help TLDR serve the world's leading tech companies with consistency and excellence.

In this role, you will:

  • Lead, mentor, and grow a high-performing team of sellers focused on enterprise accounts and multi-channel partnerships.

  • Set the strategic vision for TLDR's key accounts function from territory planning, vertical coverage, segmentation, and growth motions.

  • Build repeatable processes for forecasting, pipeline management, renewal strategy, expansion, and client success.

  • Establish executive relationships with senior marketing leaders across cloud, AI, DevTools, cybersecurity, and enterprise software.

  • Develop frameworks and playbooks your team uses to execute complex multi-newsletter, multi-quarter partnerships.

  • Partner with Account Management Leadership, Agency Leadership, Operations, Product and Talent teams to align resources and ensure we deliver best-in-class sponsorship performance.

  • Analyze trends, category performance, and whitespace to inform long-term revenue strategy and product evolution.

  • Advocate for TLDR externally by representing TLDR in high-stakes conversations, large opportunities, and strategic negotiations

What Success Looks Like

  • The Key Accounts team becomes a predictable, high-output revenue engine with strong acquisition, renewal and expansion performance.

  • Your leadership enables TLDR to form multi-quarter and annual partnerships with the most influential tech brands.

  • Sales processes are standardized, documented, efficient, and seamlessly used across the entire organization.

  • Your team consistently exceeds targets while maintaining high client satisfaction and operational excellence.

  • TLDR is seen in the market as a strategic, consultative partner; not just a media vendor — due in part to your leadership.

  • You elevate the broader revenue organization with better tools, clearer communication, and stronger cross-functional alignment.

About You

You're an experienced sales leader who has built and scaled enterprise revenue teams at high-growth media businesses.

You know how to coach sellers, create clarity, build structure, and drive growth through people, systems, data-driven decision making, repeatable motions and long-range strategy.

Primary leadership strengths:

  • 7–12+ years in enterprise sales with 3–5+ years leading a team

  • Experience managing and developing high-performing account executives

  • Strong background in multi-channel media, sponsorships, or B2B marketing programs

  • Proven ability to build scalable processes, reporting frameworks, and sales infrastructure

  • Executive presence and confident leading conversations with CMO, VP Marketing, and senior brand leaders

  • Strategic decision-maker with the ability to zoom out for vision-setting and zoom in to diagnose root causes

Additional builder/operator skills:

  • Ability to design and roll out new playbooks, SOPs, and team structures

  • Familiarity with revenue planning, forecasting models, and KPI definition

  • Strong cross-functional instinct and strength in collaborating with ops, AM leadership, agency leadership, and marketing.

  • Comfortable leading through ambiguity and shaping a fast-growing sales org and culture

  • Ability to spot patterns across industries and develop long-term vertical strategies

Nice-to-haves:

  • Experience selling to cloud, AI, DevTools, or cybersecurity buyers

  • Background in media, newsletters, B2B SaaS, or performance-based ad products

  • Exposure to early-stage, rapidly scaling environments where systems are evolving

You're Not a Fit If You…

  • Prefer to stay IC rather than lead and develop a team

  • Need heavily defined processes instead of building and refining them

  • Avoid tough revenue decisions or shy away from accountability

  • Want a slow pace or prefer layers of hierarchy and structure

Why You'll Love It

Compensation: $145, ,000 OTE

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 Macbook Air M4s. 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.

Press and Publications

  • Inc story on how TLDR was founded

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