Full-Time
Lead AI Engineer
Posted on 8/15/2025
Bestpass
51-200 employees
Toll management for commercial fleets
No salary listed
Remote in USA
Hybrid
 AI & Machine Learning (2) |
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- 7+ years building backend or infrastructure systems, with 3+ years production experience in AI/ML
- Worked and built AI applications: we’ve built MCP servers, LangChain, RAG
- Experience with LLMs, computer vision, or real-time event processing
- Strong system design and technical leadership skills
- Ability to move fast in ambiguity, and bias toward delivering working software
- Knowledge of Python, Go, TypeScript
- Familiarity with GCP, AWS, Postgres, Redis, Kafka
- Experience with MLFlow, dbt, Dagster, LangChain, Triton Inference Server
- Write and ship production code daily (Python, Go, TypeScript)
- Architect and scale core components of our AI/data infrastructure
- Collaborate cross-functionally with product, design, compliance, and customer support
- Set technical direction for other engineers, vendors, and contractors
- Present your roadmap and results directly to executives and the board
- Build and own the feature store, model CI/CD, evaluation harnesses, and observability stack across all AI efforts
- prior work in logistics, tolling, transportation, or regulated domains
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
Simplify's Take
What believers are saying
- Insight Partners investment accelerates growth and acquisitions.
- Hired CPO Shay Demmons and CMO Scott Chao on March 26, 2024.
- Transflo partnership expands toll management in logistics.
What critics are saying
- E-PASS Fleet undercuts with zero-fee model in Florida since 2023.
- TSOA TollPass365 captures Texas share via E-ZPass in 2024.
- Geotab builds in-house toll module post-2024 integration.
What makes Bestpass unique
- Bestpass offers 100% U.S. toll road coverage with single invoicing.
- Toll Genius integrates with Geotab for discrepancy alerts and heat maps.
- Acquired Drivewyze and Fleetworthy for safety-compliance suite.
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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
/PRNewswire/ -- Bestpass-Fleetworthy Solutions, the leader in toll management, safety, and compliance solutions, today announced it has acquired Drivewyze, the...
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
Toll management solutions provider Bestpass is working with telematics creator Geotab to help commercial fleets better manage and monitor tolls to reduce expenses.
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
/PRNewswire/ -- Bestpass, the leading toll management and payment platform for commercial vehicles, announced today that it has acquired Fleetworthy Solutions,...