Sales Development Representative 2.0 (Chicago/Midwest or New York City/Northeast Based)

Are you a former teacher with business experience looking for your next challenge in the education space? Do you love building relationships and creating a buzz?

At Goalbook, our mission is to empower teachers to transform instruction so that ALL students can succeed. We partner with 1,100+ school districts in 48 states, working closely with district and school leaders to create scalable change to instructional practice. We're looking for a talented and motivated individual to join our growing team.

This is not your typical SDR role! At Goalbook, we call this role Lead Development and Engagement – it’s a unique role that is a true partner to our field sales team, focused on engaging school district leaders in the early stages of the sales process. You will consultatively build relationships with district administrators as their first point of direct contact with Goalbook to discover their challenges and educate them on our solutions.

Key Responsibilities High-Quality Pipeline Generation & Top-of-Funnel Execution - Execute targeted outreach (outbound and inbound) aligned with defined Ideal Customer Profiles (ICPs) and go-to-market priorities. - Engage district leaders who have expressed prior or current interest in Goalbook to guide them through the early stages of the buyer's journey: discover needs, articulate our value proposition, nurture relationships, and schedule demonstrations. - Book high-quality discovery meetings for the field sales team that effectively convert into a qualified pipeline. - Consistently meet or exceed expectations for the number of meetings booked and pipeline generated. - Maintain focus on relevance, preparation, and value creation in every interaction. - Actively engage in coaching, feedback, and skill-building opportunities. - Demonstrate rapid learning and improvement in core competencies, including messaging, discovery, and objection handling. - Attend national and regional conferences, providing support to regional Partnerships team members as required. - Travel is required in this role – 20% travel estimated.

Required Skills & Experience - 2+ years teaching experience - 2+ years of experience in services or sales, including side hustles - Excellent interpersonal, organizational, and persuasion skills - Entrepreneurial spirit

Desirable Skills & Experience - 2+ years instructional coaching or school leadership experience

Benefits - $60-80k salary range, based on experience and location, plus commission on new revenue, for a total compensation range of $90-115k in the first year - Quarterly commission based on sales in the region - Medical, dental, and vision coverage - Safe Harbor 401k matching - Flexible Time Off policy and work schedule - Goalbook Family and Medical Leave - Goalbook Universal Basic Income - A truly motivated, passionate, and fun team.

We’re collectively interested in helping you grow in your career.

Contact Submit an application addressed to Nathaniel Rossoff and provide your cover letter, resume, LinkedIn profile, and how you heard about us. This role is remote, but ideally based in the greater Chicago Metro area or New York City, or in cities in the Midwest or Northeast within 45 minutes of a major airport. Applicants will not be considered without a cover letter.