Senior Automation Engineer

Position Summary

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.

Essential Duties and Responsibilities

• 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

Knowledge / Skills / Abilities (KSA’s)

• 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 designs, tradeoffs, and automation logic to both technical and non-technical stakeholders.

Minimum Qualifications

• 7+ years of experience in software engineering, automation engineering, or systems engineering
• Proven experience designing and building production-quality automation systems
• Strong Python expertise with backend and automation system design
• Experience with API integrations and system-to-system connectivity
• Experience with web automation (Playwright, Selenium, or equivalent)
• Experience with PDF parsing, OCR, and email processing
• Experience implementing AI or LLM-based automation with strong system understanding
• Experience with cloud platforms (AWS and/or Google Cloud)
• Direct experience working within insurance agencies or insurance operations
• Strong understanding of insurance workflows and carrier interactions
• Ability to work fully on-site in Tamarac, FL