Enterprise Account Executive - RethinkEd

RethinkFirst • Chicago, IL

6d • Remote

About The Position

At Rethink Ed, we believe learning should bring out the best in everyone. As the 2020 CODiE Award Winner for Best Social Learning Program for Students, 2021 Winner for Best Student Learning Capacity-Building Solution, and 2022 Cool Tool EdTech Finalist for Vizzle, we bring cutting-edge strategies to administrators, educators, students, parents, and caregivers to support effective, high-quality education of the whole child. Our evidence-based, technology-driven solutions are developed and delivered by leading experts in Social and Emotional Learning, Behavior Management and Special Education.

RethinkEd is seeking an Enterprise Account Executive to lead sales efforts with the nation’s largest and most complex school districts. This role is designed for an experienced seller who understands how large urban districts operate, how they transact, and how decisions are made across multiple departments, funding sources, and stakeholder groups. The Enterprise Account Executive owns a small number of high-value districts and is responsible for managing multiple, concurrent opportunities within each account. Success in this role requires deep account planning, disciplined execution, and the ability to multithread relationships across executive, programmatic, and operational stakeholders.

Requirements

• Deep understanding of large, urban school district structures and decision-making and Ability to manage long, complex sales cycles with multiple parallel opportunities
• Strong account planning and opportunity orchestration skills
• Comfortable qualifying, prioritizing, and sequencing deals within a single account
• Skilled at aligning multiple stakeholder priorities to a cohesive district narrative and confident engaging senior leaders while maintaining momentum with stakeholders
• Data-driven approach to managing sales, with experience using CRM systems and productivity tools.
• 7+ years of sales experience, preferably in K–12 education, EdTech, or complex SaaS environments
• Demonstrated success selling into large and urban school districts
• Experience managing $1M+ quotas and enterprise-level accounts
• Proven ability to manage multiple opportunities within a single large account
• Strong understanding of district procurement, contracting, and funding structures
• Bachelor’s degree or equivalent professional experience

Responsibilities

• Achieve or exceed a $1M+ annual quota through new and expanded opportunities within enterprise districts
• Build and manage a robust, multi-opportunity pipeline within each assigned district
• Expand RethinkEd’s footprint across departments, programs, and initiatives in large and urban school systems
• Establish trusted relationships with senior district leaders and functional owners across Special Education, MTSS, Student Services, Curriculum & Instruction, and related areas
• Navigate complex procurement, contracting, and funding processes common to large districts
• Partner closely with Customer Success, Services, Marketing, and Enablement to drive long-term district success, renewals, and expansion

Benefits

• Mission-driven organization making a meaningful difference in the lives of students and educators.
• Collaborative, growth-oriented culture that values innovation and accountability.
• Competitive compensation package with performance-based incentives.
• Comprehensive benefits, including health, dental, vision, retirement plan, and paid time off.
• Remote-first workplace with flexibility and national reach.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Number of Employees: 5,001-10,000 employees