Regional Account Executive (Chicago)

About the Role

As 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. This is a true field sales role, requiring in-person relationship building with superintendents, communications directors, and other district decision-makers.

Responsibilities

• Prospect independently within an assigned geographic territory, including cold outreach, door-to-door district visits, conference presence, and relationship cultivation.
• Own the sales cycle for all new business, from initial discovery through demo, proposal, negotiation, and close, with support from marketing demand generation.
• Build and manage your pipeline through a combination of self-sourced prospecting and SDR and marketing-generated leads.
• 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 by surfacing 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.
• Experience in multi-product selling.
• Comfort calling on and presenting to executive-level stakeholders (superintendent experience a strong plus).
• Strong communication skills, both verbal and written.
• High personal accountability and ownership of territory and results.
• Willingness and ability to travel extensively within an assigned region (estimated 75% travel in region).
• CRM proficiency (Salesforce preferred).

Qualifications

• Experience selling into K-12 or broader public sector is a plus, but not required.

Pay

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

Benefits

US Employee Benefits:

• Comprehensive medical, dental, vision, and life insurance coverage.
• Retirement 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.

Why Apptegy

Join a team that’s committed to your success. At Apptegy, we’re passionate about creating an environment where you can do your best work and find true fulfillment. We believe in investing in our people—both professionally and personally—because your well-being drives our collective impact. Apptegy champions the thoughtful integration of AI to empower our teams and processes.