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System1

Director of Enterprise Sales

System1

. Own one or more verticals, including fleet and telematics, logistics and delivery, healthcare, insurance, telecom, retail, or field-service SaaS .

Posted 10/15/2026full-timeRemote • United StatesLead💰 $175,000 - $200,000 per yearWebsite

About the role

Key responsibilities & impact
  • Own one or more verticals, including fleet and telematics, logistics and delivery, healthcare, insurance, telecom, retail, or field-service SaaS
  • Build net-new pipeline through outbound prospecting
  • Run the full enterprise sales cycle: discovery, technical qualification, commercial structure, procurement, and close
  • Partner with the Solutions Architect on benchmarks and proofs of concept
  • Sell on economics and terms, including cost savings, caching rights, route matrices, and flexible enterprise contracts
  • Bring prospect feedback to product so the roadmap reflects the market
  • Work directly with the VP of Sales and company leadership
  • Close deals with CTOs and VPs of Engineering for MapQuest’s enterprise mapping platform

Requirements

What you’ll need
  • 10+ years closing enterprise B2B deals with a track record of hunting net-new logos
  • Sold location APIs or SDKs, including geocoding, navigation, routing, or address validation, to engineering leaders
  • Deep knowledge of the Google Maps Platform and Mapbox licensing landscape
  • Network of buyers in logistics, telematics, healthcare, insurance, telecom, retail, or adjacent markets
  • Ability to generate your own pipeline
  • Comfortable with multi-year and pooled-commitment contracts and the related procurement process
  • Bonus: experience beating Google or another incumbent
  • Ability to work in one of the following states: Connecticut, Georgia, Illinois, Massachusetts, Missouri, New Jersey, New York, North Carolina, Ohio, Oklahoma, Pennsylvania, Tennessee, Texas, Virginia

Benefits

Comp & perks
  • Target OTE of $350K to $400K with uncapped variable, strong accelerators, and a defined ramp
  • Competitive salary + bonus + equity
  • Generous PTO + 11 company holidays
  • Open sick time
  • 100% covered Medical, Dental, Vision for employees
  • 401k with match
  • Health & Dependent Care Flex Spending Account
  • Paid professional development
  • Leadership & growth opportunities
  • Virtual company and team building events
  • Remote, US
  • Travel as needed for prospects and events