Top Sales Jobs in Chicago, IL

Partner with Account Executives to shape deal strategy, run discovery, deliver customized product demonstrations, and map customer challenges to technical solutions. Support RFIs/RFPs, analyze competitive positioning, and act as a cross-functional liaison to Product, Engineering, and Customer Success to drive measurable outcomes for mid-market customers.

Designs, delivers, and measures enablement programs for Downmarket Networks and SDR teams. Gathers field intelligence, builds AI-enabled learning tools, run trainings and coaching, partners with global enablement, and ensures programs drive measurable GTM outcomes.

Designs and delivers enablement strategy and programs for Mid-Market GTM teams. Gathers field intelligence, builds AI-enabled enablement solutions, runs large-scale training and coaching, partners with global enablement peers, and measures program impact to drive sales performance and quota attainment.

Lead governance and administration of Outreach and AI-enabled sales tooling, build and optimize sequences, run experiments and analyze performance, drive cross-functional adoption and change management, and measure business impact on prospecting efficiency and pipeline generation.

Design, deliver, and measure sales enablement programs for Enterprise GTM teams. Collect field intelligence, create AI-enabled enablement tools, run training and coaching, partner with global enablement peers, and manage end-to-end program execution to drive quota attainment and sales effectiveness.

Lead a 100+ offshore account management and sales organization to drive Net ARR growth through upsell, cross-sell, and strategic renewals. Hire and coach frontline managers, build scalable processes, partner with Product/Marketing/Onboarding, use analytics to track KPIs, and act as escalation for complex deals.

Lead pre-sales engagements for Motive's largest customers, shaping deal strategy with Strategic AEs, delivering tailored demos, responding to RFPs/RFIs, designing technical solutions and integrations, and acting as a trusted advisor to executive stakeholders.

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.

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.