Account Executive

Role Overview

Rookly is hiring a full-time AE to drive new customer acquisition and expand our footprint across schools and school networks. This is a high-ownership role for a detail-oriented, self-directed salesperson who thrives in a fast-paced startup environment and genuinely enjoys building relationships with educators and school leaders.

Key Responsibilities

• Own the full sales cycle from prospecting through close
• Manage dozens of concurrent deals across school systems
• Conduct product demos and sales presentations
• Build strong relationships with school administrators, teachers, and decision-makers
• Travel to conferences, partner schools, and events (25–50% of the year)
• Collaborate cross-functionally with marketing, product, and leadership
• Contribute beyond sales as the company scales (strategy, partnerships, ops)

Required Qualifications

• 2+ years of experience in sales (SDR, AE, or AM background)
• Strong communication skills with customers of all backgrounds
• Comfortable managing a high volume of active deals
• Deep familiarity with U.S. and Canadian regions and geography
• Highly independent and self-motivated
• Willingness to travel up to 50% of the year

Preferred Qualifications

• Curiosity about the entire sales lifecycle, from prospecting to account management
• General interest in chess, sports, or competitive academics
• Knowledge of public, charter, and independent school systems
• Experience working with students or educators
• Interest in growing beyond a traditional sales role within a startup

Why Join Rookly

• Work at the intersection of education, competition, and technology—help shape a category-defining platform in scholastic esports & academics
• High ownership, fast growth, and real opportunity for career expansion
• Direct impact on thousands of students nationwide—everything we build is oriented around giving students a more educational, engaging experience
• Independence and flexibility in your work. As a small team, we hire people we can trust to make good judgments and then give them the freedom to approach challenges the way they think best
• Health, dental, and vision insurance