Account Executive, ChessKid

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 200M+ 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 ChessKid

ChessKid, the world’s leading online chess platform for kids and schools, is on a mission to make chess accessible, fun, and educational for every child. We partner with schools and districts across the U.S. to provide engaging, standards-aligned chess experiences that build problem-solving, resilience, and critical thinking skills.

About You

We are seeking a driven and consultative Account Executive (AE) to join our K–12 sales team, focusing on new business sales, building relationships with school and district leaders, and expanding ChessKid’s footprint across the U.S. As a sales professional with a passion for EdTech, K–12 education, and B2B software, you know how to engage principals, administrators, and district leaders to spark excitement about innovative classroom tools. A background in teaching or school leadership is a bonus, but your strength lies in building relationships and driving sales.

Motivated by challenges, you enjoy discovery conversations and bring creative solutions that address schools’ needs. You bring energy, curiosity, and persistence to every interaction and are eager to learn, grow, and be coached. Most of all, you see this role as an opportunity to make a lasting impact in education while building a meaningful career in EdTech sales.

What You'll Do

• New Business Sales
• • Own the full sales cycle from prospecting to close with K-12 districts, schools, and educational organizations.
  • Identify, engage, and qualify leads through outreach, events, referrals, and inbound opportunities.
  • Deliver compelling presentations and demos tailored to administrators, principals, and district leaders.
• Pipeline Management and Revenue Growth
• • Consistently build and manage a healthy pipeline of opportunities to achieve and exceed quota.
  • Execute land-and-expand strategies to grow ChessKid adoption within districts.
  • Partner with leadership on territory planning and account prioritization.
• Account Setup and Customer Handoff
• • Ensure smooth onboarding of new customers, working with the Sales Coordinator and Customer Success team.
  • Clearly document customer needs, goals, and implementation details in the CRM.
• Renewals and Expansion
• • Collaborate with Customer Success to ensure satisfaction and identify upsell/renewal opportunities.
  • Build long-term relationships that establish ChessKid as a trusted instructional and enrichment partner.
  • Own the renewal accounts assigned to you, keeping the relationship strong and positioning ChessKid for winning renewals and potential expansion inside existing accounts
• Collaboration and Communication
• • Use Slack, CRM, and other sales tools to stay aligned with cross-functional teams.
  • Share market insights, competitor intelligence, and customer feedback with leadership to inform GTM strategy.
  • Contribute to team meetings, trainings, and process improvements.

Preferred Skills

• 2–3 years of sales experience, ideally in EdTech, SaaS, or K–12 education markets
• Background in K–12 education (teaching, administration, or re