Lead Platform Configuration Analyst

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

Role Summary

As a Policy Configuration Analyst, you own the full lifecycle of our AI-augmented policy delivery model for configuring hundreds of insurance products across global partners. Your mission is to move beyond manual processes by executing an AI-first configuration strategy. This includes gathering requirements, managing the policy build portfolio, directing the Policy Agent with structured inputs, and acting as a fluent Python practitioner to supervise, validate, and correct the agent's output. You will also develop comprehensive automated testing, build custom agent skills to automate repeating build patterns for shared tooling, own post-launch resolution, and ensure accurate documentation.

Key Responsibilities:

• Requirements & Discovery: Own the requirements gathering process for every policy build. You know which stakeholders to engage, which questions surface the information you actually need, and how to structure what you learn into clear requirements. You work with technical and GTM teams; resolving ambiguity early, chasing down what is missing, and documenting requirements in a form that needs no follow-up.

• Portfolio Ownership: Manage a concurrent portfolio of policy builds across sprint cycles across the team. Maintain a clean backlog with delivery estimates that hold, and give transparent status updates without being chased. 

• Policy Configuration: Translate your requirements into structured inputs that the Policy Agent can build from. You are responsible for directing the agent clearly enough that it produces correct configuration output, and for validating the Python it writes. The Policy Agent builds in Python and you supervise that output as a fluent Python practitioner. You can read what the agent produces, identify where it has gone wrong, and correct it. You own the result, not the keystrokes.

• Testing: Build and execute comprehensive test plans for all policy configurations prior to production deployment. Build and maintain automated test suites using our internal tooling across multiple demographic and scenario variations.

• Agent Ecosystem Development: Build custom skills and workflows within our existing agent ecosystem to automate repeating build patterns. Identify opportunities to push more of the pipeline to automated execution and contribute every improvement back to shared tooling. When you solve a build problem, you close it for everyone.

• Post-Launch Ownership: Your responsibility doesn't end at go-live. You own the resolution of post-launch bugs and change requests — triaging issues, coordinating fixes, and seeing them through to closure. Partners and internal teams will come to you when something isn't working, and you are the person who gets it resolved.

• Documentation: Keep product and configuration documentation accurate and current across the full build lifecycle. Good documentation is not a finishing task — it is how the next build starts faster and how institutional knowledge stays in the team rather than in someone's head.

What You Will Bring:

• The Technical Foundation: 5 years in a technical analyst, platform engineering, or configuration role. You can write Python, read an API spec, interpret a JSON response, and debug a broken booking flow without needing to escalate.

• The Practitioner Mindset: You aren't just a user of AI; you are a builder. You have hands-on experience building agents, automated workflows, or custom tools

• The Builder Mindset: You aren't just someone who uses the tools; you build on top of them. You have hands-on experience with APIs (Postman, cURL), test automation frameworks, and the instinct to deploy AI Agents or automate anything you do more than twice.

• The Translator Ability: You possess the rare ability to meet non-engineering stakeholders where they are, create a desire for progress, and then translate their needs into technical, engineering-ready specifications.

• Analytical Precision: You are strong numerically. You can read pricing requirements, interpret actuarial inputs, and validate financial structures without switching off - you enjoy solving interesting puzzles! 

Proficiencies and Attributes:

• Innate Technical Curiosity: You know what AI models dropped this week and have already tried them. You don't wait to be onboarded to the Platform Agent — you read the documentation before the meeting.

• Bias for Action: You encounter a blocker and you resolve it. You bring solutions to standup, not problems. You prefer a rough first build over a perfect brief.

• Systemic Pattern Recognition: You hate doing the same thing twice. When you build a new policy configuration, you are already thinking about how to template it for the next ten.

• Self-Sufficient: Ambiguity does not stall you. You identify what you need, find it, and move. You escalate when genuinely blocked — not to offload thinking.

• Collaborative but Independent: You build trusted relationships with Insurance, Actuarial, Data, and Partnerships teams. But you do not need to be managed. You manage yourself.

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 PTO. Taking time out is important for our teams to enjoy life and stay fresh.

• 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 base salary range of C$135,000 to C$175,000 annually.