Remote opportunity at
Bestpass by FleetworthySenior Software Engineer - AI
Bestpass by Fleetworthy is seeking a Senior Software Engineer - AI for its AI Platform team to build AI agents, shared platforms, and internal tooling. Fleetworthy…
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About This Role
Bestpass by Fleetworthy is seeking a Senior Software Engineer - AI for its AI Platform team to build AI agents, shared platforms, and internal tooling. Fleetworthy provides a technology suite focused on fleet readiness, encompassing toll management, weigh station bypass solutions, and safety and compliance tools that support millions of drivers and vehicles across North America. This remote position involves designing and launching AI features for external and internal users,…
Job Description
Bestpass by Fleetworthy is seeking a Senior Software Engineer - AI for its AI Platform team to build AI agents, shared platforms, and internal tooling. Fleetworthy provides a technology suite focused on fleet readiness, encompassing toll management, weigh station bypass solutions, and safety and compliance tools that support millions of drivers and vehicles across North America.
This remote position involves designing and launching AI features for external and internal users, developing an enterprise context layer with permission-aware access, and constructing automated workflows. The engineer will provision underlying infrastructure, manage deployments, handle ongoing monitoring and cost evaluation, and mentor peers. The team relies heavily on coding agents as a primary method for software development, requiring the ability to break down tasks, review agent outputs, and utilize automated tests and continuous integration.
This role suits an experienced engineer with a strong background in production software delivery, artificial intelligence applications, and modern DevOps practices who can operate independently on a small team.
Responsibilities
- Ship production software frequently in small increments and lead projects end to end from specification to launch
- Develop and deploy AI agents and features for customer and internal use
- Build and expand the enterprise context layer including connectors, retrieval systems, permission enforcement, and Model Context Protocol access
- Create shared tooling and establish practices to help other engineering teams build with agents
- Determine whether an agent or deterministic workflow is appropriate and construct the chosen solution
- Provision and run underlying infrastructure such as environments, pipelines, and deployments
- Translate ambiguous challenges from product, support, and engineering into defined requirements
- Manage production systems post-launch by handling monitoring, evaluations, cost tracking, and failure management
- Mentor team members and other engineers across the organization
Requirements
- Demonstrated experience frequently shipping software to production and owning it after release
- Proven track record of delivering AI agents or AI features into production environments
- Proficiency in Agentic Software Development Life Cycle utilizing coding agents as the primary building method
- Advanced proficiency in Python and TypeScript
- Hands-on experience with LLM APIs, Model Context Protocol, and agent frameworks
- Experience with retrieval systems including search, RAG, and permission-aware data access
- Experience applying evaluations and data to determine readiness and functionality before shipping
- DevOps experience encompassing Docker, Kubernetes or managed container platforms, infrastructure as code like Terraform, and CI/CD pipelines
- Experience operating production services with observability tools like Datadog, alerting, secrets and identity management, and incident response
- Proficiency in SQL and PostgreSQL
- Strong live communication skills along with the ability to work independently
Qualifications
- Background in fleet operations, transportation, or logistics
- Experience with Databricks including Unity Catalog or Genie
- Familiarity with enterprise search connectors such as Confluence, SharePoint, Jira, Slack, and vector databases
- Experience with identity and access control for services and agents
- Familiarity with workflow orchestration or automation platforms
- Experience with Azure including App Service, AKS, and Azure DevOps, or AWS
Core Skills
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