---
title: 'Billing Specialist at Fleetworthy'
canonical: 'https://feeny.ai/job/billing-specialist-fleetworthy-edmonton-ec5exjbbfst9'
type: 'job'
last_seen: '2026-09-08'
---

# Billing Specialist at Fleetworthy 

- **Company:** Fleetworthy 
- **Location:** Edmonton, Canada
- **Work type:** hybrid
- **Posted:** 2026-08-17
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/bestpass/jobs/4705372006

## 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/).

Job Purpose: The Billing Specialist/Senior Billing specialist is responsible for leading the end-to-end billing process for Fleetworthy's customers, ensuring billings are complete, accurate, timely, and consistent with contractual and operational requirements. Reporting to Assistant Corporate Controller, Canada, Canada, this role servers as a key point of contact for billing-related matters and works cross-functionally to research and resolve billing discrepancies and customer inquiries.

The role also supports the integrity of the billing process through reconciliations, data, analysis, and reporting, identifying exceptions and opportunities to improve billing accuracy, controls, and processes. The successful candidate will demonstrate strong ownership, attention to detail, analytical skills, and a customer-focused approach while working collaboratively across the organization.

## Key Accountabilities

- Billing Operations
- Lead the end-to-end billing process to ensure customer billings are complete, accurate, timely, consistent with contractual and operational information.
- Own the identification and resolution of billing exceptions, coordinating with relevant stakeholders to resolve issues before or after billing.
- Customer & Internal Support
- Serve as a primary point of contact for billing-related inquiries from customers and internal stakeholders.
- Research questions and discrepancies, coordinate with the appropriate teams, and facilitate timely and accurate resolution.
- Billing Reconciliations and Controls
- Perform and support reconciliations between billing systems, operational data, customer records, and financial information to identify discrepancies and maintain the integrity and completeness of billing data.
- Data Analysis and Reporting
- Analyze billing and operational data to identify trends, anomalies, missing information, and potential billing issues.
- Prepare and maintain reporting that provides visibility into billing accuracy, exceptions, unresolved items, and other relevant metrics.
- Cross-Functional Coordination
- Work collaboratively with Finance, Sales, Customer Success, Operations and other teams to obtain information required for accurate billing and resolve billing-related matters.
- Act as a bridge between the underlying operational data and the billing process.
- Process Improvement and Documentation
- Support the development, documentation, and continuous improvement of billing processes and controls.
- Identify opportunities to improve efficiency, data quality, automation, and the overall customer billing experience.
- Month-End and Financial Support
- Provide billing-related information, reconciliations, analysis, and supporting documentation required for month-end closing, financial reporting, audit, and other Finance activities
- Collections Support
- Assist with collection activities, including follow-up on outstanding customer balances and coordination with relevant stakeholders to support timely resolution.
- Payment Application Support
- Assist with the application of customer payments and related account reconciliations to ensure payments are accurately reflected against outstanding invoices.
- Ad Hoc Support
- Assist with ad hoc projects, analysis, and other initiatives as required.

## Qualifications and Core Competencies

- Bachelor's degree or diploma in Accounting, Finance, Business Administration, or a related field, or equivalent relevant experience
- 3-5 years of billing/billing operations experience
- Experience leading end-to-end billing processes
- Oracle NetSuite or similar ERP experience preferred
- Strong analytical and problem solving
- Strong reconciliation and data-analysis capabilities
- Strong customer service and communication skills
- Ability to collaborate cross-functionally and drive issues to resolution.
- Intermediate-to-advanced Excel Skills

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 

- [Senior Software Engineer](https://feeny.ai/job/senior-software-engineer-fleetworthy-edmonton-ktacemy44kfm) — Edmonton, Canada
- [Fleet Compliance Associate](https://feeny.ai/job/fleet-compliance-associate-fleetworthy-madison-wq6cbyrek9aq) — Madison, WI
- [IT Support Specialist](https://feeny.ai/job/it-support-specialist-fleetworthy-edmonton-wsg853r1ta30) — Edmonton, Canada
- [Business Analyst](https://feeny.ai/job/business-analyst-fleetworthy-edmonton-e85z33p0h65t) — Edmonton, Canada
- [R&D Imaging Specialist](https://feeny.ai/job/r-d-imaging-specialist-fleetworthy-edmonton-0gz77gcct8a8) — Edmonton, Canada
- [Platform Engineer](https://feeny.ai/job/platform-engineer-fleetworthy-edmonton-03dgkxgp5tm6) — Edmonton, Canada
- [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-wisconsin-9xsq9ns3sqgk) — Wisconsin
- [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-new-york-fg5sbpm1vvsx) — New York, NY
- [Field Service Technician](https://feeny.ai/job/field-service-technician-fleetworthy-georgia-kys7trmtx5e1) — Georgia
- [Provider Operations Coordinator](https://feeny.ai/job/provider-operations-coordinator-fleetworthy-united-states-g92qtnadcb7m) — United States, OR