Top Tech Jobs & Startup Jobs in Chicago, IL

The Regional Director, Strategic Accounts leads sales strategies, manages a team, and ensures revenue and execution efficiency in a high-profile territory.

Owns the development, implementation, and optimization of scalable sales enablement programs, including onboarding, continuous learning, sales readiness, manager enablement, content, sales plays, and platform adoption. Partners with Sales, Marketing, Product, Revenue Operations, and GTM teams to improve sales efficiency, pipeline velocity, win rates, and revenue attainment. Uses CRM and enablement data to measure impact, identify improvements, and support cross-functional business priorities.

Serves as a strategic advisor to Cengage customers, building relationships, driving product adoption, developing success plans, providing training, resolving escalated issues, conducting health checks, and identifying renewal and upsell opportunities. The role manages customer outcomes and revenue retention across an assigned territory, requiring strong communication, analysis, technical explanation, and prioritization skills. Travel by air and car is required 20–30% of the time.

Supports corporate financial planning, budgeting, forecasting, reporting, and investment decisions. Builds financial models and projections, analyzes business performance and opportunities, identifies efficiency improvements, prepares executive materials, supports investor reporting, and streamlines planning processes using AI-enabled tools. Collaborates with FP&A teams and business partners to evaluate revenue, expenses, profitability, and organizational initiatives.

Supports product strategy, market launch readiness, and go-to-market execution for CTE K12 products. Analyzes customer needs, market dynamics, competitive landscapes, and field feedback to develop positioning, messaging, personas, and sales enablement assets. Partners with Product, Sales, Marketing, Content, and Learning teams on roadmap inputs, packaging, pricing, launches, collateral, demos, and consistent customer-facing communications.

Develops and improves higher education course materials and digital learning experiences using learning science, instructional design, research, and market insights. Advises authors, reviews content quality and alignment, designs accessible and inclusive digital content, supports content creators and vendors, and collaborates across editorial, marketing, product, and production teams. The role also establishes content guidelines, develops authoring talent, and monitors emerging education technology and learning trends.

The Regional Director, Strategic Accounts directs revenue performance and account strategy, leading a team to execute strategic initiatives and drive growth in higher education sales.

Own strategic higher-education accounts, including forecasting, multi-year planning, contract negotiations, renewals, expansion, and revenue growth. Build executive relationships with academic and administrative stakeholders, lead institutional change management, and advise customers using enrollment, usage, pricing, and adoption data. Drive new business development, customer value realization, and program success while coordinating with sales, customer success, marketing, channel, and operations teams. Travel to customer meetings, conferences, and partner events 35–50% of the time.

Operationalize workforce funding programs by administering ETPL listings, supporting partner onboarding, maintaining Salesforce records, resolving funding inquiries, documenting procedures, producing reports, researching public funding opportunities, and improving scalable workflows. The role coordinates across Product, Enrollment, Student Support, Marketing, Finance, and Sales while ensuring compliance, data accuracy, partner communication, and consistent support for funded enrollments.

Leads and mentors UX designers, researchers, and product managers; integrates user-centered design into product development; drives innovative experiences; conducts user research; establishes UX standards; evaluates initiative effectiveness; and promotes collaboration, inclusion, and continuous improvement.