Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with Account Executives to shape enterprise deal strategy, deliver tailored demos, design technical solutions and integrations, respond to RFIs/RFPs, and act as a trusted advisor across technical and executive stakeholders while collaborating with Product, Engineering, and Customer Success to drive adoption and win strategic displacement opportunities.

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 the Workforce Management product suite, manage a team of Product Managers, define customer-centric strategy and requirements, conduct market/customer research, partner with EPD and GTM teams, measure product performance, and drive growth and adoption. Travel ~25%.

Manage and grow enterprise customer accounts (150-999 vehicles) through strategic account plans, upsells, renewals, product demos, adoption initiatives, and cross-functional coordination. Serve as primary contact, monitor account health, maintain CRM records, conduct business reviews, and provide accurate forecasting to drive customer retention and revenue expansion.

Sell Motive's fleet hardware and software to large State, Local, and Education agencies. Develop account plans, win RFPs, run complex proofs-of-concept, partner with Sales Engineering and Product, and manage executive relationships to meet revenue quotas while providing product and market feedback.

Lead operational strategy and execution for Onboarding, Ramp, and Bridge readiness programs. Design scalable frameworks, manage logistics and stakeholder handoffs, track KPIs, build reporting, and continuously improve learner outcomes to accelerate seller productivity.

Build and maintain sales KPI dashboards, perform recurring and ad-hoc sales performance analyses, model efficiency drivers (churn, LTV:CAC, pipeline coverage), create executive insights, partner with GTM leaders, and automate/reporting processes to scale Sales operations.

Lead and scale a team of product specialists supporting strategic solution categories. Define engagement models, prioritize coverage, coach on discovery, demos, technical validation and executive communication, create reusable plays and assets, partner with Sales, Product, and Product Marketing, and hire/onboard specialists to improve win rates and category health.

Lead pre-sales for large Public Sector customers: shape deal strategy with Account Executives, deliver tailored demos, design technical solutions and integrations, respond to RFIs/RFPs, and coordinate cross-functional teams to win and implement enterprise deals.

Lead enterprise sales efforts targeting Fortune 500 prospects across the Eastern U.S., build C-suite relationships, win RFPs, collaborate with internal teams, demonstrate product integrations, exceed revenue quotas, and use market and customer analytics to drive strategic account growth.