Top Tech Jobs & Startup Jobs in Chicago, IL

Own the full enterprise sales cycle, from prospecting and relationship development through RFPs, MSA negotiations, and closing. Target large organizations with recurring transportation needs, build senior executive relationships, secure long-term contracts, expand accounts, and collaborate with account management and operations teams. The role also involves developing outbound sales strategies, navigating procurement processes, demonstrating the platform, researching market trends, and achieving ambitious revenue targets.

Leads complex, cross-functional client launches, technology implementations, operational changes, regulatory rollouts, and urgent mobilizations. Establishes PMO standards, project charters, governance, reporting, risk management, budgets, schedules, and change-management processes. Facilitates executive and cross-functional meetings, drives accountability without formal authority, develops SOPs and training materials, and supports the long-term PMO operating model.

Own sourcing for complex enterprise transportation opportunities, including scope evaluation, cost modeling, supplier strategy, operator selection, negotiations, and feasibility assessment. Partner with Sales and Operations to develop competitive proposals, manage handoffs, resolve supply challenges, maintain supplier relationships, and improve sourcing effectiveness using data and market intelligence. The role requires strong analytical, commercial, negotiation, relationship-building, and organizational skills.

Provide customer support through email and phone, resolve and escalate issues, monitor live transportation trips, coordinate responses to disruptions, communicate updates, document interactions in Sprinklr, educate customers on DOT rules, and collaborate with drivers and internal operations teams. The role requires flexible night and weekend availability, strong organization, calm problem-solving, and adherence to service-level agreements.

Lead strategy and roadmap for CharterUP's pricing systems, partnering with engineering and data science to build pricing infrastructure, run experiments, define metrics, and translate strategy into product specifications to improve marketplace performance and operator/customer outcomes.