Description review

Ad Sales Director

Chess.com · Remote (USA) · back to the listing

HR standards

55/100

needs work

Title ↔ description

88/100

strong

Reads as

Sales Representative

100% confident

What this role officially is

commercial sales representative — ESCO, the EU occupation classification

Commercial sales representatives represent a company in selling and providing information on goods and services to businesses and organisations.

Also known as: field sales representative, technical and commercial sales executive, field sales executive, sales and marketing consultant, business development representative, technical and commercial sales representative

How others title the same work

Large employers

  • EHR Principal Sales Executive, HCLS US Providers Amazon.com
  • Channel Partner Sales Executive Canonical
  • Embedded Devices Software Solution Sales Account Manager Canonical
  • Embedded Devices Software Solution Sales Manager (APAC) Canonical
  • Embedded Devices Software Solution Sales Manager (Americas) Canonical

Startups

  • Account Executive (Full Cycle) AviaryAI
  • Founding GTM / AEs Balance
  • Business Development / Sales Intern Blaze
  • Sales Intern Blaze
  • Account Executive Blee

What the listing never says

  • 17 bullet points. Long requirement lists deter qualified candidates, who read them as hard gates. Scope clarity
  • No pay range published. Candidates cannot tell whether applying is worth their time. Pay transparency

The listing, marked up

Nothing in the wording of this listing tripped a check. The scores above still judge how complete and coherent it is.

About You

You are an experienced digital ad sales professional who has worked with top advertising agencies and brands. You have a deep knowledge of direct sales for both web and mobile platforms. You understand how to build and grow a direct sales business, from product to data to marketing to client management. You have a strong network of digital ad buyers - both from agencies and brands - and are comfortable proactively generating new leads and responding to RFPs. You are analytical and creative. You are as much driven by growing revenue as you are by creating a positive experience for our chess community and our advertising partners.

What You’ll Do

• Lead our direct ad sales business, owning the strategy and execution
• Sell Chess.com’s web and app advertising solutions, including programmatic direct, sponsorships, custom packages, and new-to-market formats
• Own the end-to-end sales process including marketing, prospecting, negotiations, close, execution and account management
• Build market awareness of Chess.com’s direct ads business, by growing relationships with brands and agencies
• Partner with our Business Development team to generate custom solutions for partners
• Work with Product, Engineering and Data to identify and develop that ad solutions that are attractive to the market and compliant with our brand guidelines

Preferred Experience/Skills

• 8+ years of experience in direct digital sales, with a strong track record of growing revenue
• Deep understanding of the digital ad ecosystem, both web and mobile
• Existing relationships with leaders at agencies and brands
• Comfort with building a business from scratch with limited existing processes and infrastructure in place
• Strong ability to think strategically and creatively, while also passionate about rolling up your sleeves and executing
• Excellent communication and presentation skills
• Bachelor’s degree from an accredited university
• Chess player and/or enthusiast
• Lifelong learner

About the Opportunity

• This is a full-time or contract opportunity depending on your location
• We are 100% remote (work from anywhere!) - but USA timezones are strongly preferred for this role due to timezone alignment and business needs

About Us

Chess.com is one of the largest gaming sites in the world and the #1 platform for playing, learning, and enjoying chess.

We are a team of 600+ fully remote people in 60+ countries working hard to serve the global chess community. We are here to support 250M+ chess players worldwide with the best possible product, content, and tools to serve the community!

We are a tech company. A gaming company. A content company. And we do it all with passion and commitment to the game. Above all we prize our mission-driven, flat, life-celebrating, no-corporate culture, and we look forward to meeting you and learning more about what you can bring to the team.

How this was produced

Highlights are found by rule, not by a model: each one is a phrase matched at a known position, and every note is a template we wrote. The two scores come from a typed-decision model (Jev) that reads the listing against the official role definition and real listings for the same role, and returns probabilities rather than prose — it never writes any of the words on this page, and never chooses what to highlight.

Deterministic penalty applied to the HR score: 8 points (from 63 before penalties). Reviewed 21 Sep 2026.