Top Sales Jobs in Chicago, IL

Manage and grow institutional and retirement client relationships, coordinate onboarding with internal teams, identify upsell opportunities, represent Inspira at conferences and meetings, maintain client communications and reporting, and drive strategic plans with Sales Managers and partners to retain and expand business.

Owns strategic enterprise sales for consumer-directed healthcare benefits, managing named accounts and complex 9+ month sales cycles. Responsibilities include stakeholder mapping, discovery, business-case development, technical demos, procurement and legal coordination, forecasting, and closing high-value B2B partnerships. The role requires executive communication, multi-threaded relationship building, technical integration fluency, and experience with HSA, HRA, FSA, benefits platforms, or related markets.

Manages assigned healthcare client accounts, serving as the primary contact for questions, concerns, renewals, and retention. Builds client relationships, resolves issues, coordinates installations, monitors product performance and key metrics, identifies plan efficiencies, and develops service solutions. Collaborates with internal teams, consultants, brokers, and account members to improve customer satisfaction and achieve revenue, membership, and earnings objectives. Requires 10–15% travel.

The Sales Executive is responsible for building business in middle markets, managing relationships, and overseeing all business development efforts in assigned territories.

Drive revenue by developing relationships with title companies, CRE firms, brokers, attorneys, and financial professionals. Execute territory-based business development plans, manage full sales cycle from prospecting to onboarding, represent Accruit at industry events, collaborate with internal teams, and maintain CRM pipeline and forecasts to grow 1031 exchange and CRE-related business.