Director of Enterprise Sales, MapQuest Platform

About the role:

MapQuest has been a household name for 30 years. What most people do not know is that we also run an enterprise mapping platform used by companies like Verizon, Walgreens, Hertz, Quest Diagnostics and the USDA for geocoding, routing, address validation, and map tiles at scale. We are building that B2B business into the growth engine of our parent company, System1.

This is a director-level, full-cycle, net-new enterprise sales role (individual contributor). You will own a set of verticals, build your own pipeline, and close deals with CTOs and VPs of Engineering who are paying too much for Google Maps, Mapbox, etc. You will work directly with the VP of Sales and a dedicated Solutions Architect, and you will have the attention of company leadership, because this business is a priority.

Please note this role is a remote role, and can work in the following states: Connecticut, Georgia, Illinois, Massachusetts, Missouri, New Jersey, New York, North Carolina, Ohio, Oklahoma, Pennsylvania, Tennessee, Texas, Virginia.

What you will do:

• Own one or more verticals (fleet and telematics, logistics and delivery, healthcare, insurance, telecom, retail, or field-service SaaS) and build net-new pipeline through outbound prospecting.

• Run the full enterprise sales cycle: discovery, technical qualification, commercial structure, procurement, close.

• Partner with our Solutions Architect on benchmarks and proofs of concept that win the technical evaluation.

• Sell on economics and terms: meaningful cost savings vs competitors at volume, full-term caching rights, a 10K x 10K route matrix, and flexible enterprise contracts.

• Bring what you hear from prospects back to product so the roadmap reflects the market.

What we are looking for:

• 10+ years closing enterprise B2B deals with a track record of hunting net-new logos.

• You have sold location APIs or SDKs (geocoding, navigation, routing, address validation) to engineering leaders and know the Google Maps Platform and Mapbox licensing landscape cold.

• You bring a network of buyers in logistics, telematics, healthcare, insurance, telecom, retail or adjacent markets.

• You generate your own pipeline and like it that way.

• Comfortable with multi-year and pooled-commitment contracts and the procurement process behind them.

• Bonus: you have beaten Google or another incumbent and can share stories about that.

Why this is a great opportunity:

• A product with a real, provable edge against the market leaders on price and terms.

• A business that company leadership has made a priority, with investment to match.

• A small team: your work is visible and your input shapes the roadmap.

• A lean, modern sales motion. We lean on AI for research, prospecting, and prep so sellers spend their time with buyers, not in spreadsheets. If you already work that way, good; if you are curious, you will learn fast here.

• Target OTE of $350K to $400K with uncapped variable, strong accelerators, and a defined ramp.

• Remote, US. Travel as needed for prospects and events.

What we have to offer:

• 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

The U.S. base salary range for this full-time position is $175,000 - 200,000 + bonus + equity + benefits. Our salary ranges are determined by role, level, and location. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position across all US locations. Within the range, individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training. Your recruiter can share more about the specific salary range for your preferred location during the hiring process. Please note that the compensation details listed in U.S. role postings reflect the base salary only, and do not include bonus, equity, or benefits. Equal Employment Opportunity: System1 provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. This role is a fully-remote role, and can work in the following states: Connecticut, Georgia, Illinois, Massachusetts, Missouri, New Jersey, New York, North Carolina, Ohio, Oklahoma, Pennsylvania, Tennessee, Texas, Virginia. SECURITY NOTICE: Please be aware that fraudulent individuals or organizations may pose as System1 Recruiters or Hiring Managers in an attempt to solicit personal or financial information. All legitimate System1 career opportunities are published directly on our official website, www.System1.com. Authentic emails from our recruiting team will only come from an official @system1.com email address. System1 will never ask candidates for money, banking information, processing fees, or equipment purchases during any stage of the recruitment process.