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 185M+ 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’re a proactive, detail-oriented, and resourceful executive assistant with a knack for anticipating needs before they arise. You have exceptional communication skills. You are able to coordinate complex schedules, prioritize tasks effectively, and handle confidential information with discretion. You thrive in fast-paced environments, love problem-solving, and are always looking for ways to improve processes and drive efficiency. You enjoy collaborating with others, are tech-savvy, and want to grow within a company that encourages your personal and professional development. Most importantly, you love making things happen and ensuring that the leadership team is supported in the best possible way.

What You’ll Do

Manage the CTO’s Calendar & Meetings
You’ll be the mastermind behind the CTO’s schedule, ensuring that 1:1s, team check-ins, and impromptu meetings are seamlessly coordinated. You’ll help prioritize meetings that align with strategic goals, while also making sure the CTO has time to focus on what matters most. You’ll prepare agendas and track follow-ups to keep the team and leadership aligned.
Coordinate and Drive Special Projects
You’ll be the point person for special projects that span across teams and departments. From coordinating product demos to organizing cross-functional initiatives, you’ll ensure that projects stay on track, timelines are met, and communication flows smoothly. You’ll collaborate closely with leadership and team members to make things happen efficiently.
Own Email & Communication Management
With your organization and attention to detail, you’ll manage the CTO’s inbox, prioritize messages, and create systems to filter key communications. You’ll flag important emails, respond where appropriate, and draft thoughtful replies to vendor and partner inquiries. You’ll also help summarize key email threads and ensure follow-ups happen on time.
Curate and Digest Company Updates
Stay in the loop with key updates across the organization and distill this information into digestible, actionable reports for the CTO. You’ll create concise summaries of departmental updates, product milestones, and company-wide initiatives, ensuring the CTO is always well-informed and can make data-driven decisions.
Capture Insights & Key Moments
You’ll act as the CTO’s "eyes and ears" within the organization, collecting important insights, metrics, and highlights from meetings, Slack conversations, and reports. You’ll turn these moments into valuable content for presentations and strategy reviews. You’ll ensure key insights aren’t missed and that they’re used to drive future success.
Support Strategic Reporting & Presentations
You’ll work hand-in-hand with the CTO and other leaders to create and organize presentations, reports, and other strategic documents. From monthly updates to company-wide all-hands decks, you’ll ensure all materials are aligned with leadership priorities and are delivered on time. You’ll help craft narratives that bring our data and insights to life.
Own and Improve Processes
You’ll continuously look for ways to improve processes—whether it’s streamlining meeting agendas, creating templates for reports, or building better workflows for cross-functional communication. You’ll bring your insights into how to make everything run more efficiently, allowing the leadership team to focus on what matters most.
Drive Professional Growth
You’ll have the opportunity to grow alongside the leadership team. Whether through taking on higher-level projects, learning from experienced executives, or shaping your role to fit your strengths, you’ll be a key player in both the CTO’s success and your own professional development. This is a role where your contributions will directly impact the company’s success and your own growth trajectory.

Preferred Skills

Experience as an executive assistant supporting C-suite executives in a fully remote environment, ideally within tech or large-scale companies
Strong organizational skills with the ability to manage complex calendars and prioritize competing demands
Advanced proficiency in office tools (e.g., Google Workspace, Notion, Slack, Zoom) as well as productivity tools
Ability to understand and associate concepts and technical terms across all subjects in engineering
Experience in preparing and organizing large presentations and reports using data from many sources(e.g., Google Slides, Sheets, Figma, Github, JIRA, Grafana, Datadog, and more!)
Exceptional communication skills, both written and verbal, with the ability to synthesize information quickly and communicate effectively across all levels of the organization
Strong problem-solving skills, with a proactive mindset and the ability to work independently
High level of professionalism, tact, and discretion when handling confidential information
Ability to adapt quickly to changing priorities and handle multiple projects simultaneously

About the Opportunity

This is a full-time position
We are 100% remote (work from USA or CA!)
This role is open to applicants who can work in American timezones.

You can learn more about us here:

https://www.chess.com/article/view/how-chess-com-virtual-team-works-together
https://www.chess.com/about

We look forward to meeting you!

Chess.com

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Executive Assistant to CTO