Full-Time

Billing Specialist

Posted on 8/17/2026

Bestpass

Bestpass

51-200 employees

Toll management for commercial fleets

No salary listed

Edmonton, AB, Canada

Hybrid

Bachelor's

Category
Accounting (1)
Required Skills
ERP
Data Analysis
Excel/Numbers/Sheets

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Requirements
  • A bachelor's degree or diploma in Accounting, Finance, Business Administration, or a related field, or equivalent relevant experience.
  • Three to five years of billing or billing operations experience.
  • Experience leading end-to-end billing processes.
  • Strong analytical and problem-solving skills.
  • 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.
Responsibilities
  • Lead the end-to-end billing process to ensure customer billings are complete, accurate, timely, and 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • Provide billing-related information, reconciliations, analysis, and supporting documentation required for month-end closing, financial reporting, audit, and other Finance activities.
  • Assist with collection activities, including follow-up on outstanding customer balances and coordination with relevant stakeholders to support timely resolution.
  • Assist with the application of customer payments and related account reconciliations to ensure payments are accurately reflected against outstanding invoices.
  • Assist with ad hoc projects, analysis, and other initiatives as required.
Desired Qualifications
  • Oracle NetSuite or similar enterprise resource planning experience.

Bestpass provides toll management services for commercial fleets in the United States. It uses vehicle transponders to automatically pay tolls, then consolidates charges into a single invoice with online reporting to assign costs to specific vehicles. The company differentiates itself with nationwide coverage on major U.S. toll roads and strategic tolling partnerships that streamline payments for fleets. Its goal is to reduce administrative work and toll costs so fleet operators can focus on their core logistics.

Company Size

51-200

Company Stage

Growth Equity (Venture Capital)

Total Funding

$19.1M

Headquarters

Town of Colonie, New York

Founded

2001

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Simplify Jobs

Simplify's Take

What believers are saying

  • Drivewyze acquisition on 2025-10-03 expands Bestpass into weigh-station bypass and compliance.
  • Fleetworthy launched shared access, centralized vehicle management, and FleetworthyGO on 2026-05-22.
  • Transflo partnership and Geotab integrations widen distribution across 65,000 fleets and 800,000 drivers.

What critics are saying

  • New York State Thruway Authority's 1% surcharge fight threatens Bestpass margins and customer pricing.
  • Fleetworthy's 2026 brand unification can confuse customers and disrupt product adoption.
  • PrePass and Verra Mobility pressure pricing; private toll managers face disintermediation risk if states insource billing.

What makes Bestpass unique

  • Fleetworthy unified Bestpass, Drivewyze, and CPSuite into one fleet-readiness suite on 2026-02-19.
  • Bestpass covers 100% of major U.S. toll roads with one monthly statement.
  • Geotab integration now forecasts future toll spend and manages transponders inside MyGeotab.

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Benefits

Flexible Work Hours

Paid Vacation

401(k) Retirement Plan

401(k) Company Match

Wellness Program

Employee Referral Bonus

Company News

PR Newswire
Aug 7th, 2024
Bestpass-Fleetworthy Solutions Acquires Drivewyze to Create Industry's Only Suite for Safety, Compliance, and Efficiency

/PRNewswire/ -- Bestpass-Fleetworthy Solutions, the leader in toll management, safety, and compliance solutions, today announced it has acquired Drivewyze, the...

PR Newswire
Mar 26th, 2024
Bestpass Adds Innovation And Growth Executives

ALBANY, N.Y., March 26, 2024 /PRNewswire/ -- Bestpass, Inc., the leader in toll management solutions and major innovator in safety and compliance solutions for commercial fleets, today announced two key additions to its leadership team. Bestpass is pleased to welcome Shay Demmons as Chief Product Officer and Scott Chao, as Chief Marketing Officer. These strategic hires will aid in Bestpass' commitment to scale its service offerings and network integrations for commercial fleets and owner operators."We're thrilled to have Shay and Scott join the team at Bestpass," said Tom Fogarty, CEO of Bestpass. "We set out to build out our Innovation and Growth teams by attracting accomplished leaders as our first C-Level executives in Product and Marketing. Scott and Shay bring extensive and dynamic work experience, both in and outside the transportation industry. As we continue to grow the Bestpass brand and bring forth new solutions for our customers, I am confident that their leadership will play a pivotal role in driving our success."Chao joins Bestpass as CMO with deep experience in growing companies through strategy and transformational improvements

FreightWaves
Feb 7th, 2024
Bestpass, Geotab collaborate on toll-telematic integration

Toll management solutions provider Bestpass is working with telematics creator Geotab to help commercial fleets better manage and monitor tolls to reduce expenses.

Yahoo Finance
Feb 7th, 2024
Bestpass Announces New Integration With Geotab

Geotab customers using Bestpass can now access new toll activity data and reporting features through a single interfaceALBANY, N.Y., Feb. 7, 2024 /PRNewswire/ -- Bestpass, Inc., a comprehensive payment platform provider and the leader in toll management solutions for commercial fleets, today announced a new integrated offering within the Geotab ecosystem that will enable Bestpass customers access to first-of-its-kind toll data and reporting tools in their Geotab account. Geotab, a global leader in connected transportation solutions, provides telematics – vehicle and asset tracking – capabilities to over 50,000 customers in 160 countries. The integration will allow fleets and owner operators the ability to gain new insight into toll activity to more effectively manage tolls and identify opportunities to reduce toll expenses.Bestpass LogoAccording to David Long, Head of Product at Bestpass, the company developed its Toll Genius data reporting system to integrate with telematics providers, such as Geotab, to enable Bestpass to synchronize and share toll and telematics data through a single interface.With this integration, Bestpass customers can leverage accurate vehicle data and GPS location through Geotab and match that information with toll charges received from their Bestpass account via the MyGeotab interface. If there's a discrepancy between vehicle GPS location and the toll a vehicle received, it's reported. This feature makes it easier for customers to identify and investigate the issue, dispute an inaccurate toll charge or violation, and reduces the risk of disputes over toll charges with drivers and customers.The integration also has a new toll activity reporting feature that shows a high-level heat map that allows fleets to identify hot spots for toll spend

PR Newswire
Nov 28th, 2023
Bestpass Acquires Fleetworthy Solutions

/PRNewswire/ -- Bestpass, the leading toll management and payment platform for commercial vehicles, announced today that it has acquired Fleetworthy Solutions,...