--- title: 'Customer Care Representative at Fleetworthy' canonical: 'https://feeny.ai/job/customer-care-representative-fleetworthy-madison-rxb3xyrvn3cg' type: 'job' last_seen: '2026-11-10' --- # Customer Care Representative at Fleetworthy - **Company:** Fleetworthy - **Location:** Madison, WI - **Work type:** onsite - **Posted:** 2026-11-04 - **Last confirmed live:** 2026-11-10 - **Apply:** https://job-boards.greenhouse.io/bestpass/jobs/4724175006 ## Job description Fleetworthy offers the only complete technology suite for fleet readiness, uniting safety and compliance, toll management, and weigh station bypass solutions. We help fleets streamline operations, control costs, and operate with confidence. Trusted by 75% of the top fleets in North America, Fleetworthy offers the most adopted toll management solution and largest weigh station bypass network. Going beyond regulatory requirements, our safety and compliance capabilities strengthen safety programs and enable proactive audit readiness. We support millions of vehicles and drivers and are recognized across the industry for innovation and leadership. Fleetworthy is shaping the future of fleet readiness with AI-enabled, connected fleet technology that keeps drivers safe, fleets compliant, and operations running at peak efficiency. Learn more at [fleetworthy.com](http://fleetworthy.com/). About the role: You’ll be the friendly, knowledgeable voice for our customers. Your job is to help carriers stay current on regulations, solve problems quickly, and leave every conversation feeling taken care of. No trucking or compliance background is required. If you like helping people and learning how things work, and solving the occasional puzzle, we’ll teach you the rest. What you’ll do: - Respond promptly to customers by phone, email, and chat - Build positive, trusted relationships with your assigned customers - Investigate and resolve questions, problems, and concerns, working with teammates to find the best outcome for the customer and the company - Use our systems to validate data and check quality every day, so customers stay compliant - Keep learning regulations and internal procedures so your guidance is accurate - Protect customer privacy by handling personal information according to our policies - Share what you learn, and contribute to a positive team across departments - Keep a consistent schedule so customers and teammates can count on you What you bring: - Customer service experience. One year is preferred, and equivalent experience counts, whether from retail, restaurants, hospitality, healthcare, or a call center - High school diploma or equivalent - Clear, friendly written and verbal communication - Good judgment, and the confidence to make decisions on your own - Comfort juggling several tasks and working with a variety of personalities - Working knowledge of Microsoft Office, especially Outlook, Word, and Excel - Curiosity and a willingness to learn new systems, changing regulations, and shifting priorities - Comfort working at a computer for most of the day Bonus, but not required: experience in trucking, transportation, compliance, or tolling. Where you’ll work: This is an in-office role at our Madison, Wisconsin location. It is not a remote position. Typical schedule is Monday-Friday, 8am-5pm. Fleetworthy is committed to fostering a diverse and inclusive culture that is respectful and welcoming of individual differences. We are proud to be an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion or belief (or lack thereof), sex, nationality, national or ethnic origin, civil status, age, citizenship status, sexual orientation, disability, genetic information, familial status, marital or registered civil partnership status, pregnancy or maternity status, gender identity, gender reassignment, military or veteran status, or any other protected characteristic in accordance with applicable laws and regulations. ## About Fleetworthy ## Company Overview - **One-liner**: Fleetworthy provides a unified technology suite for fleet readiness, combining safety and compliance, toll management, and weigh station bypass solutions. - **Entity Type**: Private (subsidiary of Bestpass, Inc.; acquired in 2023) - **Headquarters**: Albany, New York, United States - **Founded**: Not publicly available (brand launched in 2024/2025 through a rebrand of Bestpass, Fleetworthy Solutions, ExpressTruckTax, and Drivewyze) - **Founders**: Not publicly available ## Core Business - Primary industry: Fleet management software for commercial trucking and logistics. - Target customers: B2B – fleet managers, owner-operators, human resources, and finance teams in transportation. - Mission or purpose: "Simplify road safety and fleet operations through integrated, innovative technology" – helping fleets stay compliant, efficient, and safe. ## Products & Services - **[Safety & Compliance]**: Digital tools for regulatory compliance, driver monitoring, and audit readiness. - **[Toll Management]**: Nationwide toll coverage (Complete Pass+) with a single device, reducing violations and administrative burden. - **[Weigh Station Bypass]**: Access to 925+ locations across 48 states and provinces, with expedited inspection capabilities. These are delivered as a **Connected Suite** that integrates all products under one platform. ## Market Standing - **Valuation/Market Cap**: Not disclosed. - **Key Metric**: Annual Revenue of $37.4M (estimated by LinkedIn) and Total Funding of $105.8M across multiple rounds. - **Notable Investors/Partners**: The Argentum Group (led early round), Susquehanna Growth Equity (talent source), and partnerships with 90% of the largest fleets in North America. - **Growth Signals**: Headcount grew 213.9% YoY to 225 employees; recent rebrand unified four legacy brands; active job postings increased 700% YoY; AI-enabled features being rolled out. ## Competitive Advantages - Only vendor offering a complete, integrated suite for safety, tolls, and bypass – reducing the need for multiple point solutions. - Largest weigh station bypass network in North America, with 925+ locations. - Trusted by 90% of the largest fleets (e.g., Faith Technology saw 90% reduction in toll violations; RWE saw 15%+ reduction in compliance costs). - Deep domain expertise from decades of combined experience (Bestpass founded in 1993, Drivewyze in 2009, etc.). ## Strategic Focus - Unified brand strategy under Fleetworthy to cross-sell and simplify customer experience. - Investment in AI-enabled, connected fleet technology to improve real-time decision-making and proactive compliance. - Continued expansion of product features and geographic coverage (presence in Canada and India). ## Why Work Here - **Culture**: Collaborative, innovative, and fun environment with employee-led committees (Thrive, Hype, Care). Emphasis on "People First, Trust, Every Trip Matters, Always Innovating, Mindset". - **Work Model**: Offers remote, hybrid, and in-office roles. Many engineering positions are remote or hybrid (Edmonton, AB or US remote). - **Perks**: Comprehensive health/dental plans, life and disability insurance, wellness programs, Employee Assistance Program, paid time off, casual dress code, company swag, events, and learning & development programs. - **Engineering Culture**: Opportunities to work on meaningful products that impact real-world safety; stack includes modern software engineering roles (Platform Engineer, Senior Software Engineer, Manager, Software Engineering) with a focus on innovation. ## Sources 1. [fleetworthy.com](https://fleetworthy.com/) 2. [linkedin.com](https://www.linkedin.com/company/fleetworthy) 3. [greenhouse.io](http://job-boards.greenhouse.io/bestpass) 4. [fleetworthy.com](https://fleetworthy.com/resources/blog/a-new-era-in-fleet-management) ## Other roles at Fleetworthy - [Business Operations Coordinator](https://feeny.ai/job/business-operations-coordinator-fleetworthy-united-states-33ttya7f9c71) — United States, OR - [Senior Software Engineer - AI](https://feeny.ai/job/senior-software-engineer-ai-fleetworthy-canada-e0fssav7z711) — Canada - [Customer Service Representative (English/Spanish Bilingual)](https://feeny.ai/job/customer-service-representative-english-spanish-bilingual-fleetworthy-edmonton-y8zjvabn1yfc) — Edmonton, AB - [Client Service Representative](https://feeny.ai/job/client-service-representative-fleetworthy-madison-d3kzmtw535y4) — Madison, WI - [Associate Product Manager](https://feeny.ai/job/associate-product-manager-fleetworthy-edmonton-nqt4arce4mkr) — Edmonton, Canada - [Data Entry](https://feeny.ai/job/data-entry-fleetworthy-metuchen-43zetk9jdz6y) — Metuchen, NJ - [Senior Software Engineer](https://feeny.ai/job/senior-software-engineer-fleetworthy-canada-5afsetv2mme1) — Canada - [Internship - Finance](https://feeny.ai/job/internship-finance-fleetworthy-edmonton-wvanen47q8a5) — Edmonton, Canada - [Fulfillment Coordinator](https://feeny.ai/job/fulfillment-coordinator-fleetworthy-albany-6fp34na7m3a5) — Albany, NY - [Customer Care Representative](https://feeny.ai/job/customer-care-representative-hp-hood-remote-fqaj3hf2r03a)