Top Tech Jobs & Startup Jobs in Chicago, IL

Own and scale Fleetio's Deal Desk: manage deal review, approvals, discount policy, and exceptions; advise Sales/Partnerships/Finance on complex deals; analyze pricing and deal performance; build automation and AI-enabled workflows; define Deal Desk metrics and governance.

Drive new business for Fleetio by prospecting and closing mid-market customers via consultative sales, web demos, strategic outreach, negotiation, and cross-functional collaboration to grow ARR.

Drive new business sales to government and education customers by prospecting, qualifying, and closing complex SaaS deals. Develop territory plans, navigate multi-stakeholder procurement processes, run POCs, collaborate with internal partners, and consistently meet ARR targets through data-driven ROI selling and repeatable sales strategies.

Manage strategic relationships with high-value enterprise fleet customers to drive expansion ARR and NRR through upselling, cross-selling, renewals, product demos, and partnership with Customer Success; travel to customer sites as needed to identify growth opportunities.

Own retention, expansion, and net revenue growth for a portfolio of mid-market Fleetio customers. Develop and execute strategic account plans, map stakeholders, drive upsell/cross-sell and renewals, partner with Customer Success to maximize adoption, present to executives, and achieve NRR targets. Travel ~25%.

Sell Fleetio's SaaS fleet-management product to small and medium businesses. Prospect and qualify leads, run web-based demos, negotiate pricing, and close deals. Generate pipeline through outbound outreach, manage inbound leads, coordinate with cross-functional teams, and own the sales process end-to-end to drive ARR growth.