Top Sales Jobs in Chicago, IL

Manage full enterprise sales cycle for Retail accounts, prospecting and closing large SaaS deals ($1M+ ARR). Build C-suite relationships, navigate complex cross-functional stakeholders, drive account expansion, collaborate with marketing/partnerships, and use CRM tools for forecasting.

Own the full sales cycle for net-new acquisition in the Emerging Enterprise segment (1,000–2,000 employees). Prospect, generate pipeline, and close deals ($200K–$1M+ ARR) using consultative, value-first selling; coordinate cross-functional teams; maintain forecasting discipline and MEDDPICC scorecards; use Salesforce CRM and collaborate with internal partners to accelerate complex sales.

Owner of full sales cycle for Financial Services: prospecting, closing, and renewals. Hunt for new business ($50K–$500K ACV), manage and grow 8–14 accounts with Customer Success, act as strategic advisor, and collaborate with Marketing, Product, and Technical executives to deliver value-driven, data-informed engagement.

Own the full sales cycle for Scale Retail: prospect, qualify, and close new SaaS business. Act as a trusted advisor to customers, collaborate with Marketing/Product/Technical stakeholders, run consultative discovery, demonstrate ROI, and manage pipeline through data-driven outreach and iteration to accelerate large, distributed SaaS purchase decisions.

Lead and scale the global Deloitte partnership: own GTM strategy, drive joint sales with regional teams from prospecting to close, commercialize Deloitte services, measure and optimize pipeline quality, and coordinate cross-functional enablement and tooling to convert partnership activity into revenue.