---
title: 'Senior Software Engineer at Fleetworthy'
canonical: 'https://feeny.ai/job/senior-software-engineer-fleetworthy-canada-5afsetv2mme1'
type: 'job'
last_seen: '2026-10-20'
---

# Senior Software Engineer at Fleetworthy 

- **Company:** Fleetworthy 
- **Location:** Canada
- **Work type:** remote
- **Posted:** 2026-10-02
- **Last confirmed live:** 2026-10-20
- **Apply:** https://job-boards.greenhouse.io/bestpass/jobs/4718519006

## 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/).

## Responsibilities

- Leading Team and projects
- Collaborate with product team on technical feasibility and story breakdown
- Design, develop, and maintain web applications using Django and FastAPI
- Build and integrate RESTful APIs
- Implement scalable ETL/data transformation workflows using Databricks or similar platforms
- Write efficient and well-structured SQL, and manage PostgreSQL database schemas
- Develop and execute unit tests, and participate in writing integration and end-to-end tests
- Troubleshoot, debug, and resolve complex issues across the stack
- Ensure code quality through automated testing and code reviews
- Collaborate with cross-functional teams to implement features and business logic
- Communicate effectively with both technical and non-technical team members
- Provide guidance to junior developers

## Requirements

- Senior-level full stack developer with Dev Lead Experience
- Strong interactive communication skills — speaking live with others is extremely important for this role
- Advanced skills with Python
- Demonstrated ability to design, build, and ship agentic workflows (agents, tool use, MCP) that measurably speed up delivery and raise quality. Mentors others on building effectively with AI and on reviewing and testing what it produces.
- Experience with frameworks such as Django, Flask, or FastAPI
- Experience with REST APIs
- Experience building data pipelines and ETL processes with tools like Databricks
- Proficiency with React and modern JavaScript/TypeScript
- Proficient in SQL and PostgreSQL, including schema design and query optimization
- Strong debugging and problem-solving skills
- Experience with unit testing, test-driven development, and frameworks such as pytest
- Familiarity with version control in a Git-based system (GitHub, GitLab, BitBucket)
- Familiarity with build pipelines, e.g., GitHub Actions, GitLab, BitBucket, Azure DevOps
- Familiarity with software ticketing systems or processes, e.g., Jira, Solar, ServiceNow
- Willingness to spend a significant portion of onboarding -and perhaps ongoing time- in collaborative team programming settings

Preferences

- Experience with Redis for caching and queuing
- GraphQL API design and integration
- Experience with Docker and orchestration tools like Kubernetes
- Familiarity with cloud platform services such as Azure or AWS
- Experience with geospatial data and functions (e.g., Geocoding API, H3 grid system, PostGIS)
- Experience with observability tools (Grafana, Datadog) and comfort working from traces, logs, and metrics

Additional Information

- May be requested to attend an in-person interview and/or orientation and training upon hire

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)

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