Top Edtech Sales Jobs in Chicago, IL

Leads City Year Chicago’s individual giving program, targeting approximately $900,000 in annual revenue. Builds donor pipelines, cultivates and solicits leadership-level and multi-year gifts, oversees Red Jacket Society fundraising, manages alumni and volunteer relationships, and partners with organizational leadership and development operations. The role also coordinates donor events, tracks activity in Salesforce, forecasts revenue, and represents the organization at community functions. It is primarily in person with local travel required.

Drive K-12 sales across Illinois and Wisconsin by developing territory plans, meeting revenue goals, presenting professional development solutions, and building relationships with school district decision-makers. Manage accounts, expenses, market intelligence, and consultative sales activities using Salesforce, Salesloft, Outlook, Google, Excel, and Word. This remote field role requires a home office in the territory, a valid driver’s license, and approximately 50–75% overnight travel.

Generate qualified sales leads for Account Executives by prospecting K-12 district administrators, curriculum and CTE leaders, teachers, and school stakeholders. Conduct outbound phone, email, and LinkedIn outreach, create email sequences and campaigns, schedule discovery meetings, cultivate upgrades among free users, and secure referrals. The role requires organized, independent execution and strong communication skills in a fast-paced, in-office environment.

Drive North American private events business by sourcing leads, quoting services, planning event logistics, coordinating staffing, supporting on-site execution, analyzing event outcomes, and building lasting client relationships. Manage the transition from sales to implementation and account management while maintaining accurate event data. The role requires event-industry expertise, strong organization, customer focus, travel, weekend availability, and comfort working on-site at events.

Own and grow strategic banking and insurance accounts for a technology services organization. Build executive relationships, develop account expansion strategies, cross-sell cloud, data, AI, transformation, modernization, and managed services, and identify revenue opportunities. Partner with presales, consulting, solutioning, and delivery teams on proposals and execution. Maintain executive oversight of engagements, address concerns, and support customer satisfaction, retention, and increased wallet share.

Leads fundraising strategy and execution for an assigned regional portfolio, targeting approximately $23 million annually. Partners with regional leaders to cultivate donors, manage moves management, track pipelines, and achieve revenue goals. Oversees grant-writing workflows, donor stewardship, narratives, collateral, CRM systems, and quarterly action plans. Collaborates with development, communications, marketing, data, finance, and systems teams while engaging directly with funders and donors. The role is primarily internal-facing and includes occasional regional travel and non-traditional hours.

Contact and qualify prospective students via phone, email, and SMS; guide applicants through the enrollment process; collaborate with internal teams to ensure application progression, compliance, and student satisfaction while meeting enrollment goals.

Lead and develop a team of Sales Specialists to drive growth in higher education disciplines. Provide coaching, field support, cross-functional coordination with Marketing and Editorial, sales strategy execution, forecasting, and market feedback. Travel frequently to support sales meetings, conferences, and training; manage hiring, training, and performance of direct reports.

Drive adoption of courseware and digital learning solutions for Business & Economics programs by building pipeline, closing new business through campus engagement and virtual selling, managing accounts, maintaining CRM and forecasts, and collaborating with cross-functional teams to meet sales and market-share targets.

The Executive Director will lead K12 sales, build partnerships, establish market presence, and provide strategic insights to drive growth in the education technology sector.