Software Engineer (Agentic AI & Tooling) at Cover Genius

The Company

Cover Genius is a Series E insurtech that protects the global customers of the world’s largest digital companies including Booking Holdings, owner of Priceline, Kayak and Booking.com, Intuit, Uber, Hopper, Ryanair, Turkish Airlines, Descartes ShipRush, Zip and SeatGeek. We’re also available at Amazon, Flipkart, eBay, Wayfair and SE Asia’s largest company, Shopee. Our partners integrate with XCover, our award-winning insurance distribution platform, to embed protection for millions of customers worldwide each year.

Our team and products have been recognized with dozens of awards including by the Financial Times which ranked Cover Genius as the #1 fastest-growing company in APAC in 2020. Our diverse team across 20+ countries and many language groups commit itself to diverse cultural programs, in particular “CG Gives” which makes social entrepreneurs out of us all and funds development initiatives in global communities.

Our People are

Bold, Authentic, Purposeful and Inspired

Our People are not

Perfect, Traditional, Complacent or Cautious

About The Role

As a Software Engineer (AI & Tooling), you will own the design, development, and optimization of business-critical applications within our Internal Tooling space, with a primary focus on Agentic AI.

This role demands more than just API integration. You must have demonstrated experience building AI Agents that can perform real work. We are looking for a builder who can walk us through an agent they have created, explaining how it decomposes complex user requests into multistep workflows, how it maintains state across a conversation, and crucially, how it handles failure.

You will design agents that are not just "chatbots," but active workers capable of navigating our XCore and XPSD platforms. You will be responsible for the full lifecycle of these agents—from the architectural pattern (e.g., ReAct, DAGs) to the fallback mechanisms that ensure reliability when the AI encounters ambiguity or errors.

Key Responsibilities

• Architecting Agentic Workflows: Design and implement stateful AI Agents capable of decomposing complex, ambiguous business requests into precise, multistep execution plans. You will define how agents reason, plan, and maintain context over long-running tasks.
• Engineering for Reliability & Failure Recovery: Build robust "guardrails" and recovery mechanisms. You will be responsible for ensuring agents can detect their own failures, self-correct when tools return errors, and gracefully degrade to Human-in-the-Loop workflows when low confidence is detected.
• Tool & API Abstraction: Bridge the gap between LLMs and our internal infrastructure. You will design the "Tool Use" layer, wrapping our existing XCore and XPSD APIs into clean, well-documented functions that an AI can reliably invoke.
• End-to-End System Ownership: Own the full lifecycle of these intelligent features—from the ReactJS frontend interfaces where users chat with agents, to the Python backend orchestration, through to production deployment and monitoring.
• Evaluation & Observability: Implement comprehensive evaluation pipelines (Evals) to measure agent accuracy and performance. You will set up tracing (logging the "Chain of Thought") to diagnose why an agent succeeded or failed in a specific workflow.
• Cross-Functional Leadership: Serve as the technical lead for the AI transition within Internal Tooling. You will mentor other engineers on prompt engineering patterns, context window management, and agentic design principles.
• Continuous Optimization: Actively manage the trade-offs between model intelligence, latency, and cost. You will prototype with emerging models and frameworks to ensure our tooling remains cutting-edge.
  
  

What You Will Bring

• Core Engineering Foundation: at least 3+ years of professional software engineering experience with Bachelor's or Master's degree in Computer Science or Engineering.
• Demonstrated AI Agent Experience: You have a portfolio or GitHub history showing you have built agents that use Tools/Function Calling. You can clearly explain the architecture of these agents, specifically how they plan and execute multistep workflows to achieve a goal.
• You have used popular Agentic Development libraries like Langchain, Langraph, google-adk etc
• Resilience & Error Handling Patterns: You understand that LLMs are non-deterministic. You have experience implementing robust failure handling strategies, such as self-correction loops, retry logic for parser errors, and "Human-in-the-Loop" handoffs when the agent lacks confidence.
• Modern Python & AI Stack: Deep expertise in Python. Experience with orchestration frameworks (e.g., LangGraph, AutoGen, CrewAI, or raw OpenAI Assistants API) and vector stores (Pinecone, Chroma, etc.).
• Traceability & Debugging: Experience using tracing tools (like LangSmith or Arize Phoenix) to debug agent thought processes. You know how to inspect a "chain of thought" to understand why an agent made a specific decision.
• Full Stack Competency: Experience with ReactJS to build the interfaces where internal users interact with your agents, and the backend services that host them.
  
  

What You Will Have

• Ownership mindset: That fosters accountability throughout the organization and encourages proactive problem-solving, learning from failures while celebrating successes as collective achievements.
• Exceptional communication skills: Demonstrated through the ability to articulate technical concepts to diverse audiences and facilitate productive cross-functional collaboration.
• Pragmatic problem-solving: Strong analytical skills and a practical approach to solving complex issues.
• Curiosity & continuous learning: Passion for learning and growth.
• Influence & impact: Positively influence the technical direction of your team, driving the adoption of best practices and high standards.
  
  

Why Cover Genius?

Cover Genius not only cares about being the best in our industry, we care about our team. We’re a business that understands life can be fluid and so we flex to ensure we provide the environment to suit that. What does that mean?

• Flexible Work Environment - our teams are hybrid. We work from home on Wednesdays and Thursday and attend the office on Monday, Tuesday and Friday with flexibility around start/finish times.
• Employee Stock Options - we want our people to share in our success, we reward them with ownership for their contribution in creating a world-class company.
• Work with like-minded people who are passionate about both the work we're doing and giving back. Our CG Gives programs enables us to all become philanthropists through our peer recognition and rewards system.
• Social Initiatives - pictures speak a thousand words!
  
  

Sound interesting? If you think you have the best composition of the above, send us your resume and let's chat!

• Cover Genius promotes diversity and inclusivity. We don't tolerate discrimination, demeaning treatment of anyone, or harassment due to race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or any other legally protected status.
  
  

By submitting your application, you acknowledge that we may collect, store and process your personal data for recruitment purposes. To ensure a fair evaluation, we may use AI to assist in sorting applications, but all final decisions are made by our hiring team and no candidate dispositions are automated. We will keep your information on file for three years from the date of your application. For detailed information about how we handle your data and our use of AI, please review our full Privacy Policy.

• This position offers a cash compensation range of C$116,000 to C$145,000 annually.