Regional Account Executive (Chicago)

About the role

The RoleAs a Regional Account Executive, you will own the full sales cycle, from first conversation to signed contract, within a defined geographic territory. You will work alongside SDR and marketing support while also driving your own pipeline.

Responsibilities

• Prospect independently within an assigned geographic territory, including cold outreach, door-to-door district visits, conference presence, and relationship cultivation with superintendents, communications directors, and other district decision-makers
• Own the sales cycle for all new business, from initial discovery through demo, proposal, negotiation, and close, with support from marketing demand generation
• Navigate complex K-12 buying processes, including multi-stakeholder decisions, school board timelines, and budget cycles
• Maintain accurate CRM records to track activity, pipeline, and forecasting
• Represent Apptegy at regional and national education conferences and events
• Provide market feedback. As eyes and ears on the ground, you'll surface intel on district needs, competitive dynamics, and positioning

Requirements

• 3-6 years of field or outside sales experience, ideally in SaaS, ed-tech, or public sector sales
• Demonstrated track record of self-sourced pipeline and closed business; you know how to generate your own deals
• Demonstrated track record in multi-product selling
• Comfort calling on and presenting to executive-level stakeholders (superintendent experience a strong plus)
• Strong communication skills; you can hold a room and write a crisp follow-up email
• High personal accountability; this role requires you to own your territory and your results
• Willingness and ability to travel extensively within an assigned region (estimated 75% travel in region)
• CRM proficiency (Salesforce preferred)
• Experience selling into K-12 or broader public sector is a plus, but not required

Qualifications

• CompensationStarting base salary range $70,000 - $85,000Commission eligible

Benefits

• US Employee Benefits: Comprehensive medical, dental, vision, and life insurance coverage
• Retail 401(k) with employer match
• Health Savings Accounts (HSA) and Flexible Spending Accounts (FSAs)
• Mental Health Reimbursement
• Unlimited paid time off, including seasonal (December) company-wide time off
• Paid parental and medical leave
• MX Employee Benefits: Private medical insurance for you and your dependents
• Life insurance
• 15 days Aguinaldo Vales de Despensa Fondo de Ahorro Caja de Ahorro
• Flexible paid time off policy
• Paid travel to/from Little Rock, Arkansas for Onboarding

Pay

Starting base salary range $70,000 - $85,000 Commission eligible

Schedule

Estimated 75% travel in region