Manager, Sales - Tolling - Remote

PayNearMe, Inc.

Job Overview

Location

Santa Clara

Job Type

Full-time

Full Job Description

📋 Description

• Own and accelerate revenue in the $1B+ North American tolling market by leading a dedicated vertical team and carrying a personal quota of $3-4M ARR. You will quarterback every stage of the sales cycle—from cold outreach through signed SOW—while simultaneously coaching 3-5 quota-carrying Account Executives to do the same.
• Serve as the company’s foremost tolling authority, translating complex operational, regulatory, and financial challenges into clear ROI stories for DOTs, turnpike authorities, regional mobility agencies, and private concessionaires. You will be the voice of the customer inside our walls and the voice of our platform in boardrooms and procurement halls.
• Build and nurture a multi-tiered contact map across C-suite, operations, IT, finance, and procurement at every major tolling agency in the U.S. and Canada. Leverage existing relationships and systematically expand your network via industry associations (IBTTA, AASHTO, ITS America), conferences, and targeted outbound campaigns.
• Architect and execute a three-year strategic plan that doubles our tolling ARR. This includes market segmentation, competitive positioning, channel partnerships, and expansion into adjacent segments such as congestion pricing, managed lanes, and mileage-based user fees.
• Manage a high-performing team without bureaucratic drag. Set crystal-clear quarterly OKRs, inspect the pipeline weekly, run deal-strategy clinics, and deliver hands-on coaching that turns B-players into A-players. Foster a culture of radical candor, continuous learning, and celebration of wins.
• Run enterprise SaaS negotiations that span multi-year subscriptions, professional services, data-integration fees, and SLAs. Navigate public-sector procurement vehicles (RFP/RFQ, sole-source, cooperative contracts) and keep legal, infosec, finance, and customer success aligned so deals close on time and on terms.
• Translate field intelligence into product roadmap influence. Package customer feedback into actionable user stories that help Product prioritize features such as real-time violation processing, interoperability clearinghouses, and AI-based image analytics.
• Collaborate cross-functionally with Solution Engineering to craft demos that showcase 99.9% uptime, sub-second transaction processing, and PCI-DSS compliance. Work with Marketing to launch tolling-specific campaigns, webinars, and whitepapers that generate 30% of your pipeline.
• Report to the VP of Sales with full transparency—forecast accuracy within 5%, weekly pipeline hygiene, and a living playbook that documents winning talk tracks, objection handling, and procurement shortcuts. Present quarterly business reviews to the executive team and board.
• Travel up to 40% to client sites, industry events, and team off-sites. Balance remote leadership with in-person energy when it matters most—whether that’s closing a $1.2M deal in Austin or running a two-day SKO in Santa Clara.

🎯 Requirements

• 7+ years selling enterprise software or SaaS solutions directly into tolling authorities, DOTs, or public-sector transportation agencies with a verifiable track record of $3M+ annual quota attainment
• 2+ years managing and coaching quota-carrying sales reps in a player-coach model; demonstrated ability to build and scale high-performing teams
• Deep fluency in tolling ecosystem—concession models, back-office operations, interoperability (E-ZPass, SunPass, FasTrak), violation enforcement, and federal regulations (MAP-21, FAST Act)
• Proven mastery of public-sector procurement processes including RFP/RFQ, sole-source justifications, and cooperative purchasing contracts
• Bachelor’s degree required; MBA or PMP certification preferred

🏖️ Benefits

• Remote-first culture with quarterly team off-sites in top-tier destinations and a $1,500 annual stipend for home-office upgrades
• Uncapped commission plan with accelerators above 100% quota and equity in a high-growth SaaS company approaching unicorn status
• Comprehensive health, dental, vision, and mental-wellness coverage for you and dependents at no employee cost
• 20 days PTO, 10 paid holidays, and a company-wide week off in July and December
• Annual $2,000 professional-development fund for certifications, conferences, or executive coaching

Skills & Technologies

Onsite

Ready to Apply?

Apply Externally

You will be redirected to an external site to apply.

PayNearMe, Inc.

Visit Website

About PayNearMe, Inc.

PayNearMe operates a cash payment network allowing consumers without traditional banking to pay bills, rent, and loan installments at participating retail locations. The system converts cash into electronic payments for businesses in lending, property management, auto finance, and utilities. Users receive a barcode or payment code to complete transactions at 7-Eleven, CVS, Family Dollar, and other chains. Merchants gain guaranteed electronic settlement and compliance tracking. Founded in 2009 and headquartered in Santa Clara, California, the company serves lenders, property managers, and government agencies needing inclusive payment options across the United States.

View Company Profile