growthroles

Ad Sales Director

Chess chess.com Open · verified Sep 24, 2026
Remote US Full-time Director Account Executive

At a glance

Leadership Account Executive role at Chess. Remote, United States · full-time.

Pay not stated

RoleAccount Executive
SeniorityDirector
LocationUS
WorkplaceRemote
EmploymentFull-time
PostedSep 3, 2026 · 3w ago
Role brief

Growth Roles summary, based on the employer's posting.

What you'll do

  • Lead the direct advertising operation, setting its direction and handling execution
  • Sell web and mobile ad offerings, from programmatic direct and sponsorships to custom packages
  • Run each deal from promotion and prospecting through negotiation, delivery, and account care
  • Build agency and brand relationships while creating demand for the direct ads business
  • Develop marketable, brand-compliant ad products with Business Development, Product, Engineering, and Data

What you bring

  • At least eight years selling digital advertising directly, with documented revenue growth
  • Strong knowledge of advertising across web and mobile, plus established agency and brand buyer relationships
  • Experience creating a business with few existing processes or systems
  • Strategic thinking, creative problem-solving, hands-on execution, and strong presentation skills
  • A bachelor's degree from an accredited university

Who this fits

You’ll suit a senior digital ad seller who can generate leads, answer RFPs, grow revenue, and build a direct-sales operation. The role is remote, with United States time zones strongly preferred for alignment and business needs. It may be full-time or contract depending on your location.

From the employer

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.

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

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