Remote Edtech Sales Jobs in Chicago, IL (NOW HIRING)

Are you an educator at heart yearning to make a greater impact? Do you love building relationships and helping others succeed? Are you an advocate for technology solutions that help all learners thrive?

About Us
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.
The Role
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.

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

Qualifications & Key Competencies

• 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

Why Join RethinkEd?

• 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.

Benefits: 

• Generous health, dental, & vision benefits package
• Flexible paid time off   
• 11 paid company holidays
• 401k + matching
• Parental leave
• Access to our award-winning RethinkCare platform supporting neurodiversity in the workplace through parental success, professional resilience, and personal wellbeing.  

Location: Remote opportunities are available to candidates who reside in the following states: AL, AZ, CT, FL, GA, HI, IA, IL, IN, KY, LA, MD, MA, MI, MN, MO, MT, NC, NE, NH, NJ, NV, OH, OK, OR, PA, RI, TN, TX, VA, WA, WI, WY

Our commitment to an inclusive workplace 

RethinkFirst is an equal opportunity employer and is committed to providing a workplace free from harassment and discrimination. We celebrate the unique differences of our employees because that is what drives curiosity, innovation, and the success of our business. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, pregnancy, genetic information, disability, status as a protected veteran, or any other protected category under applicable federal, state, and local laws. Accommodations are available for applicants with disabilities. 

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Recruiting Fraud Alert: Job applicants should be aware that there are external parties posing as RethinkFirst recruiters. These scams may include fraudulent communications via social media platforms (such as LinkedIn), email, or requests to schedule interviews.  Note that any recruiting related communication you receive from RethinkFirst would come from an @rethinkfirst.com e-mail address, @applytojob.com email address (via our talent acquisition system),  ‘careers@rethinkfirst.com’ email address, and/or be found on the Rethinkfirst.com website.  Please also note that at no point during our recruitment process will we request any form of monetary payment.  If you believe that you have been a victim of job recruiting fraud, you should file a report with your local law enforcement. 

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