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Sales Development Representative 2.0

United States, Chicago 60000.00 - 80000.00 USD / Year · Job Posted March 20, 2026
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Job Description

Join Goalbook as a Sales Development Representative 2.0, where you'll use your teaching and business skills to build relationships and support school district leaders in enhancing instructional practices. This is 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.

Job Responsibility

  • Generate high-quality pipeline leads
  • Conduct targeted outreach
  • Book discovery meetings for the sales team
  • Provide consultative support to school district leaders
  • 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

Requirements

  • 2+ years teaching experience
  • 2+ years of experience in services or sales
  • Excellent interpersonal, organizational, and persuasion skills
  • Entrepreneurial spirit

Nice to have

2+ years instructional coaching or school leadership experience

What we offer

  • 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

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