Top Sales Jobs in Chicago, IL

Partners with Account Executives to support mid-market sales through discovery, customized product demonstrations, solution design, RFI/RFP responses, and value-based selling. Translates customer challenges into measurable outcomes, advises technical and business stakeholders, explains APIs and integrations, and collaborates with Product, Engineering, Customer Success, and Marketing. Requires strong communication, analytical, and problem-solving skills, plus willingness to travel 15–20%.

Supports enterprise sales by partnering with Account Executives, leading discovery, delivering tailored demonstrations, translating customer challenges into solutions, and influencing executive buying decisions. The role requires expertise in value-based selling, solutions engineering, complex enterprise sales cycles, APIs, integrations, and technical solution design, while collaborating with Product, Engineering, Customer Success, and Marketing. Travel of 30% or more is required.

Manages sales and services operations for Implementation, Installation, and Customer Education teams. Improves workflows, customer onboarding, resource allocation, and performance through data-driven analysis. Partners with Sales, Support, Product, and leadership on strategic projects, forecasting, territory alignment, QBRs, reporting, and Salesforce dashboards. Oversees recurring business processes, identifies inefficiencies, and provides operational guidance in a high-growth SaaS environment.

Own the full sales cycle for new Networks business, from prospecting and discovery through negotiation and close. Generate outbound leads through cold calling, events, and strategic outreach while meeting revenue quotas and KPI targets. Conduct demos and trials, collaborate with Sales Development, Sales Engineering, Customer Success, and senior sellers, and maintain accurate forecasts. The role requires SaaS sales experience, quota achievement, strong ownership, curiosity, and willingness to travel to tradeshows and partner events.

Leads a team of Strategic Account Executives across the Eastern region, driving enterprise sales performance, account planning, pipeline management, forecasting, revenue attainment, hiring, coaching, and enablement. Partners with cross-functional teams and directly supports high-priority prospects and strategic deal execution. Builds a high-performance sales culture and ensures consistent use of CRM tools, sales processes, and best practices.

Develop and close strategic enterprise business across the Central U.S., targeting Fortune 500 and F1000 prospects. Build C-suite relationships, develop champions, win RFPs, grow contractual business, exceed revenue quotas, and collaborate with internal account and technical teams. Demonstrate platform integrations, provide consultative insights, resolve customer problems, analyze market trends, and influence buying decisions across fleet-focused industries.

Leads a team of Strategic Account Executives selling SaaS solutions to Fortune 500 and other enterprise customers. Responsibilities include hiring, coaching, account and territory planning, pipeline management, forecasting, revenue attainment, sales enablement, CRM adoption, and direct involvement in high-priority deals. The role partners cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Customer Success, Legal, and Sales Operations.

Own the full sales cycle for mid-market fleets (50–174 trucks): prospect, qualify, demo, negotiate, and close new business. Drive outbound lead generation, meet revenue quotas, collaborate cross-functionally, manage trials, and maintain accurate forecasting.

Lead a team of Strategic Account Executives selling SaaS solutions to major enterprise customers. Responsibilities include hiring, coaching, account and territory planning, pipeline reviews, forecasting, sales enablement, KPI management, revenue target attainment, and direct involvement in high-priority deals. The role partners cross-functionally with Sales Development, Sales Engineering, Product, Marketing, Customer Success, Legal, and Sales Operations to drive strategic sales execution.

Lead and coach a team of Enterprise Account Executives on prospecting, account planning, forecasting, and closing Fortune-level accounts. Develop territory and strategic account plans, track KPIs, hire and enable talent, collaborate cross-functionally, and directly engage high-priority prospects to drive ACV and revenue goals while ensuring CRM and sales processes are followed.