Regional Account Executive (Chicago)

About this role

<div class="content-intro"><h3 class="paragraph heading3 ng-star-inserted" data-start-index="32"><strong><span class="ng-star-inserted" data-start-index="32">Who We Are</span></strong></h3> <div class="paragraph normal ng-star-inserted" data-start-index="43"><span class="ng-star-inserted" data-start-index="43">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.</span></div></div><h3><strong>The Role</strong></h3> <p>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.</p> <p>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.</p> <p>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.</p> <h3><strong>What You'll Do</strong></h3> <ul> <li><strong>Prospect independently</strong> 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</li> <li><strong>Own the sales cycle </strong>for all new business, from initial discovery through demo, proposal, negotiation, and close, with support from marketing demand generation </li> <li><strong>Build and manage your pipeline</strong> through a combination of self-sourced prospecting and SDR and marketing-generated leads.</li> <li><strong>Navigate complex K-12 buying processes</strong>, including multi-stakeholder decisions, school board timelines, and budget cycles</li> <li><strong>Maintain accurate CRM records</strong> to track activity, pipeline, and forecasting</li> <li><strong>Represent Apptegy</strong> at regional and national education conferences and events</li> <li><strong>Provide market feedback.</strong> As eyes and ears on the ground, you'll surface intel on district needs, competitive dynamics, and positioning</li> </ul> <h3><strong>What You’ll Bring</strong></h3> <ul> <li>3-6 years of field or outside sales experience, ideally in SaaS, ed-tech, or public sector sales</li> <li>Demonstrated track record of self-sourced pipeline and closed business; you know how to generate your own deals</li> <li>Demonstrated track record in multi-product selling</li> <li>Comfort calling on and presenting to executive-level stakeholders (superintendent experience a strong plus)</li> <li>Strong communication skills; you can hold a room and write a crisp follow-up email</li> <li>High personal accountability; this role requires you to own your territory and your results</li> <li>Willingness and ability to travel extensively within an assigned region (estimated 75% travel in region)</li> <li>CRM proficiency (Salesforce preferred)</li> <li>Experience selling into K-12 or broader public sector is a plus, but not required</li> </ul> <h3>Compensation</h3> <ul> <li>Starting base salary range $65,000 - $85,000</li> <li>Commission eligible </li> </ul><div class="content-conclusion"><h3 class="paragraph heading3 ng-star-inserted" data-start-index="1841"><strong><span class="ng-star-inserted" data-start-index="1841">Why Apptegy</span></strong></h3> <div class="paragraph normal ng-star-inserted" data-start-index="2151"><span class="ng-star-inserted" data-start-index="2151">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.</span></div> <div class="paragraph normal ng-star-inserted" data-start-index="2151"> </div> <div class="paragraph normal ng-star-inserted" data-start-index="2151">US Employee Benefits: </div> <div class="paragraph normal ng-star-inserted" data-start-index="2442"><span class="ng-star-inserted" data-start-index="2442">Comprehensive medical, dental, vision, and life insurance coverage</span></div> <div class="paragraph normal ng-star-inserted" data-start-index="2510"><span class="ng-star-inserted" data-start-index="2510">Retirement 401(k) with employer match</span></div> <div…