Senior Automation Engineer

Prestige Trucking Insurance is seeking a Senior Automation Engineer (AI, Systems & Infrastructure) to design, build, and own the automation systems that will fundamentally transform how the company operates. This role focuses on eliminating manual, repetitive, and error‑prone workflows across insurance operations by implementing robust, scalable automation solutions. This is a senior‑level role with full ownership over automation strategy and execution.

The Senior Automation Engineer will work directly with leadership and internal teams to understand real insurance workflows and replace them with well‑engineered automation systems. Automation at Prestige is not a side initiative—it is a critical pillar of how the business will scale. The ideal candidate brings deep technical expertise, strong insurance agency experience, and the ability to independently identify problems, design solutions, and deliver measurable business impact.

• Design and build end-to-end automation systems using Python, APIs, AI, and cloud infrastructure
• Replace manual workflows across submissions, quoting, renewals, endorsements, policy servicing, and carrier portals
• Automate workflows involving email ingestion, PDF processing, OCR, document classification, and web portals
• Build multi-step, orchestrated automation pipelines rather than one‑off scripts
• Work directly with internal teams to understand existing processes and redesign them for automation
• Develop and maintain a centralized automation platform with logging, monitoring, error handling, and recovery
• Make architecture and tooling decisions that balance speed, scalability, cost, and long‑term reliability
• Implement AI and LLM integrations where appropriate to improve efficiency and accuracy (not as a black box)
• Design systems that interface with carrier portals, agency management systems, and internal tools
• Ensure automation solutions are secure, auditable, and resilient
• Translate business workflows into technical systems with clear documentation
• Define timelines, milestones, and execution plans for automation initiatives
• Continuously identify inefficiencies and propose automation opportunities across departments

• Automation System Design – Ability to design and build scalable, maintainable automation systems that replace manual business processes.
• Python & Backend Engineering Expertise – Advanced ability to design backend services, automation pipelines, and integration layers using Python.
• API Integration & System Connectivity – Strong ability to integrate third‑party APIs, internal systems, and event‑driven workflows reliably.
• Web & Document Automation – Ability to automate web‑based workflows using tools such as Playwright or Selenium, and process PDFs using OCR and parsing techniques.
• AI & LLM Integration – Ability to apply AI and LLMs thoughtfully to real workflows, with an understanding of limitations, security risks, and failure modes.
• Workflow Orchestration & Pipelines – Ability to design multi‑step automation pipelines with orchestration, retries, error handling, and observability.
• Cloud Infrastructure Knowledge – Strong working knowledge of AWS and/or Google Cloud for hosting, scaling, and system reliability.
• Insurance Operations Expertise – Deep understanding of insurance agency workflows including submissions, quoting, binding, renewals, endorsements, and carrier interactions.
• Systems Thinking & Problem Solving – Ability to analyze complex processes, identify inefficiencies, and design complete automation solutions.
• Ownership & Execution – Ability to operate independently, define priorities, execute without hand‑holding, and deliver outcomes.
• Communication & Technical Clarity – Ability to clearly explain system…