Engineering Manager - Agentic Insights

The Company

Cover Genius is the global infrastructure for embedded protection. Active in over 60 countries and all 50 US States, we protect the customers of the world’s largest digital companies, including Klarna, Revolut, Stripe, Priceline, Agoda, Booking.com, Turkish Airlines, Tongcheng Travel, eBay, and Uber, with seamless, end-to-end experiences. Cover Genius has protected more than 73M customers globally across 240M policies with USD $3.2BN in gross written sales.

Coming off a stellar year with 40% YoY revenue growth and a recent $100M capital raise, putting our valuation at $1.9BN, we are accelerating into our next phase of growth. As part of our team, you’ll help drive our AI-first roadmap, developing hyper-personalization engines, agentic distribution, and automated claims infrastructure, while building the scalable technology powering the fast-growing $70B embedded protection market.

Our people are: Accountable, customer-obsessed, collaborative, driven

Our people are not: Passive, defensive, siloed, hesitant

About the Role:

As the Engineering Manager, Agentic Insights, you will lead the team that turns Cover Genius's cross-portfolio data into products our partners can act on. You will own two existing products — Claims Benefit Intelligence and the Sales Dashboard — and the technical roadmap beyond them that includes agentic AI features for analysts, an expanding portfolio of data products, and more.

You will have taken LLM-powered products from prototype into production, built analytics products for non-technical external users, and worked at warehouse scale. Regular collaboration with a dedicated Product Manager partner and Product, Data Platform, Data Science, Insurance Operations, the AI team and partner-facing commercial teams will be key in creating insights partners act on.

Key Responsibilities:

• Lead and grow a team of engineers building partner-facing data products, fostering technical excellence, ownership and psychological safety in line with Cover Genius values.

• Own the technical roadmap for existing data products such as Claims Benefit Intelligence and the Sales Dashboard, and for future products — including onboarding both products into the team.

• Own BrightWrite Metrics service, the metrics delivery surface queried by partners and dashboards, ensuring metric consistency, alignment with audited internal definitions, and a robust governance framework.

• Establish engineering and operational excellence for partner-facing services: reliability and latency SLOs, observability, CI/CD, IaC, testing and data quality.

• You are accountable, alongside Product, for partner engagement and the value of insights delivered — not just shipping.

What you will bring:

• 8+ years of experience in software or data engineering and 2+ years leading or managing engineering teams in a fast-paced, high-growth environment.

• Track record of building data or analytics products for external, non-technical users.

• Hands-on depth in agentic systems with experience taking an agent from prototype to a production system that has defined evaluation and guardrails

• Practical experience with Data Platforms at warehouse scale with dbt and an orchestrator such as Airflow; expert SQL and strong Python.

• Our estate spans Python/Django and BigQuery on the data and ML side, and Node.js/TypeScript on the Partner Portal side, on Kubernetes across AWS and GCP, with Terraform and Datadog — you will be comfortable leading a team that works across diverse tech stacks.

• Demonstrated experience adopting AI-assisted development practices within a team — evaluating tools, setting standards for their use, and measuring productivity and quality impact.

What you will have:

• Exceptional leadership and communication skills. You know how to inspire, motivate and develop a team of technical experts.

• Genuine product instinct. You think in terms of the decisions partners make with our data, not the features we ship — and you measure success by insights acted on, not dashboards delivered.

• Judgement to know when AI earns its place and when a well-defined metric or clear chart is the better answer. You prefer pragmatic engineering over trend-driven solutions.

• Integrity to hold a privacy or data-quality line under commercial pressure.

• Strategic mindset — you align data initiatives with business goals and manage stakeholder expectations across engineering, product and commercial functions.

• Strong problem-solving ability and a deep sense of ownership, from technical architecture through to team performance and product outcomes.

• Self-motivated and reliable, able to drive projects to completion in a fast-paced environment.

🤔 Why Cover Genius?

At Cover Genius, we create magic by turning the archaic into the extraordinary. We take one of the world’s oldest and most complex industries and reinvent it with world-class technology. Cover Genius doesn’t just disrupt legacy insurance; we make the impossible feel effortless. Our operating principles guide our mission:

• Make today matter: We deliver with urgency and excellence. We act decisively, move with intention, and hold a high bar.

• Act with accountability: We own our commitments and take pride in delivering results that move us forward.

• Grow together: We are a collective of curious minds. We learn from wins and setbacks, share knowledge generously, and elevate each other every day.

• Inspire Each Other: We push each other to think bigger and pull together to go further.

• Champion Our Customers: We lead with empathy and center the customer, turning complex disruptions into seamless moments of trust.

• Flexible Work Environment - Our teams are hybrid. We work from home on a Wednesday and Thursday and attend the office on Monday, Tuesday and Friday with flexibility around start/finish times.

• Don't just take our word for it - hear about our culture straight from our people here: story time.

Ready to make an impact? If you’re looking for a place where you’ll be challenged, trusted, and empowered, we’d love to meet you.

The Legal & Privacy Stuff

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 compensation range of C$150,000 to C$190,000 annually.