Founding Account Executive

Rookly - New York City, New York or Remote - Full time

Title: Founding Account Executive

Location: [Remote, NY]

Company Overview

Rookly is building the first national scholastic chess league. Rookly provides the match software, coordinates schedules for schools, and finds tournament directors to create a seamless experience for scholastic chess clubs. We have over 100+ schools participating and are backed by some of the top chess players in the country and ed tech investors.

Job Overview

As Rookly’s Founding AE, you will help lead sales and go-to-market alongside the founding team. While this role will embody traditional full-cycle sales, our hope is that you will be a partner in the business, and OTE + equity will be commensurate.


Prospecting and Lead Generation:

Identify and qualify leads within the education sector, namely private and charter schools; ideally by leveraging personal networks or creative outbound strategies


Lead the negotiation and closing process for sales opportunities

Create exciting demos that show Rookly’s distinct software solution

Sales Strategy and Planning

Broadly implement strategic sales plans and initiatives: this could include managing an SDR

Utilize tools to track progress and manage the efficacy of different strategies

Relationship Management

Build and maintain strong relationships with key stakeholders in schools, including administrators, teachers, and IT decision-makers.

This might include traveling to visit customers, attending conferences, or anything related to deepening our relationships with schools.

Sales Performance and Reporting

Provide regular reports and updates to founders on sales performance, forecasts, and market trends

360 view of sales data to identify new opportunities for Rookly to expand our presence 


Bachelor's degree and 3+ Years of Experience, preferably in Private and Charter School Sales

Proven a track record of meeting or exceeding sales targets.

Excellent communication, negotiation, and presentation skills, with the ability to articulate complex ideas clearly and persuasively.

Strategic thinker with strong problem-solving abilities and the ability to develop and execute effective sales strategies.

Self-motivated and results-driven, with a passion for driving growth and positively impacting education.

Proficiency in CRM software, sales tools, and MS Office suite.

Other Helpful Skills

Has experience in e-sport sales.

Loves chess.


Please contact with any questions or when you are ready to apply.

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Experience Level

Mid Level


Rookly is building online chess leagues across the country, using custom software to create an immersive student experience and a seamless administrator workflow. We believe chess competition can be treated like athletics, creating a future where chess players can be celebrated like athletes.
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