Top Sales Jobs in Chicago, IL

Leads the West region’s Mid-Market and Small Group sales team, managing approximately 10–12 direct reports. Responsibilities include coaching sellers, improving pipeline discipline, forecasting revenue, progressing deals, setting CRM and activity standards, supporting broker relationships, recruiting, onboarding, and addressing performance issues. The manager owns the region’s combined new-business target, develops sellers across consultative and transactional sales motions, and travels periodically for field coaching, client meetings, and industry events.

Leads the East region’s Mid-Market and Small Group sales team, coaching sellers, managing pipeline and forecasts, driving quota attainment, and developing talent. The role oversees approximately 10–12 direct reports, supports broker and consultant relationships, attends client and industry events, contributes to sales-model improvements, and partners cross-functionally on hiring, onboarding, performance management, and seller development.

Leads enterprise new-business growth for health and benefits solutions, including go-to-market strategy, sales team development, pipeline discipline, consultant and broker relationships, strategic employer pursuits, forecasting, and cross-functional coordination. Owns enterprise revenue targets, competitive intelligence, sales operating standards, and performance KPIs while personally supporting complex, executive-level opportunities and consultant-led RFPs.

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.

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.