Chicago, United States of America Hybrid Employment $60-80k

Goalbook is hiring a Sales Development Representative 2.0 (Chicago/Midwest or New York City/Northeast Based)

About the Role

As a Sales Development Representative, you’ll bridge your classroom experience with sales expertise to engage school district leaders and support early-stage sales efforts. Your focus will be on identifying needs, sharing relevant solutions, and setting up discovery meetings that advance district goals.

What You'll Do

  • Conduct targeted outreach—both inbound and outbound—to school districts aligned with strategic priorities and customer profiles.
  • Guide district leaders through initial conversations, helping them understand how solutions can meet their needs and improve student outcomes.
  • Schedule qualified discovery meetings for the field sales team, contributing to a consistent and high-intent pipeline.
  • Deliver value-driven interactions by staying prepared, relevant, and responsive in every conversation.
  • Travel up to 20% of the time, including attendance at regional and national education events to support partnership efforts.
  • Engage in ongoing coaching and skill development to strengthen messaging, discovery techniques, and response to objections.

Requirements

  • At least two years of experience as a classroom teacher.
  • Minimum of two years in a client-facing role involving services or sales.
  • Strong communication, organization, and influence skills.
  • Self-starter mindset with a drive to learn quickly and adapt.

Preferred Qualifications

  • Two or more years in instructional coaching or school leadership roles.

Benefits

  • Medical, dental, and vision insurance
  • Safe Harbor 401k with company match
  • Flexible Time Off and adaptable work hours
  • Family and Medical Leave support
  • Universal Basic Income program
  • Opportunities for professional growth within a passionate, mission-focused team

Work Mode

This is a hybrid position. Remote work is supported, but candidates should be based in the greater Chicago metro area, New York City, or other Midwest or Northeast cities within 45 minutes of a major airport.

Compensation

The base salary ranges from $60,000 to $80,000, depending on experience and location. With quarterly commission tied to regional sales performance, total first-year compensation can reach $90,000–$115,000.

Company Culture

The team is united by a shared commitment to equity and student success. We value diverse perspectives and lived experiences in education, and actively foster an inclusive environment where all team members can grow. Professional development is prioritized, and collaboration is rooted in purpose, curiosity, and mutual support.

Required Skills
salesrelationship buildingpersuasionorganizational skillsentrepreneurial mindseteducation sector knowledgeteaching experienceclient services salesrelationship buildingpersuasionorganizational skillsentrepreneurial mindseteducation sector knowledgeteaching experienceclient services
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About company
Goalbook

Goalbook Toolkit is a holistic solution that helps special educators develop higher-quality IEPs and implement them with more effective, specially designed instruction.

Over 10 years of research from leading institutions, including Johns Hopkins University and WestEd, shows that Goalbook improves instructional practice, increases teacher effectiveness, and boosts student outcomes.

Since 2011, Goalbook has partnered with over 1,100 districts across 47 states to enhance collaboration, improve workflows for IEP teams, and support educators with actionable resources aligned to Universal Design for Learning (UDL) and differentiated instruction.

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Job Details
Department Partnerships
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Posted 2 months ago