Regional Account Executive (Chicago)

Who We Are

At Apptegy, we are more than a tech company; we are partners dedicated to transforming how schools communicate and shape the future of education. Your work here will directly empower districts to share their stories, engage their communities, and celebrate student success. We're a team of thoughtful, high-performing individuals committed to making a tangible impact. If you're looking for a dynamic environment where you'll be supported with exceptional mentorship and resources to grow your career, come build with us.

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. You'll be in districts, in front of superintendents and communications directors, building relationships the old-fashioned way: in person. You'll prospect, qualify, demo, and close, all while becoming the face of Apptegy in your own backyard.

If you're someone who thrives on autonomy, loves being in the field, and wants to own your number end to end, this role was built for you.

What You'll Do

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

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. As eyes and ears on the ground, you'll surface intel on district needs, competitive dynamics, and positioning

What You’ll Bring

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

Compensation

Starting base salary range $65,000 - $85,000

Commission eligible

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.

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.

Apptegy champions the thoughtful integration of AI to empower our teams and processes. As we seek to understand your individual capabilities and how you might contribute, we ask that all responses to application questions and during interviews are genuinely your own. Please refrain from using AI generation tools, as our aim is to assess your authentic voice and expertise.

Equal Opportunity Employer

Apptegy is an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, gender expression, national origin, age, protected veteran or disabled status, or genetic information.