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 Senior Product Designer on our Embedded Insurance team, you'll lead the design of high-converting insurance purchase experiences that live within our partners' retail, travel, fintech, and banking platforms. You'll design the moments where customers discover, compare, and buy protection products — embedded directly into checkout flows, booking journeys, and account dashboards. Your work ships on partner websites and apps, so you'll need to balance conversion performance with seamless integration into diverse brand environments and tech stacks.

You'll own the end-to-end design of insurance offer surfaces, sales panels, product comparison flows, and post-purchase experiences that directly impact attach rate, conversion, and customer trust. If you've designed ecommerce checkout, upsell, or add-to-cart experiences, the pattern will be familiar — you'll be applying those instincts to insurance products. Working closely with Product, Engineering, Growth, and Marketing, you'll drive design strategy, build scalable and testable UI solutions, and lead rapid experimentation to deliver measurable commercial outcomes across partner integrations.

This role is AI-forward by design. You'll integrate AI tools into every phase of your workflow from using generative AI for rapid prototyping, variant generation, and copy exploration; leveraging AI-assisted research and synthesis to accelerate insight development; and applying AI within experimentation workflows to scale personalization and testing velocity. Beyond your own practice, you'll pioneer AI-augmented design methods and champion their adoption across the design team.

We're looking for someone who has already operated at a senior level, leading design work streams, mentoring others, presenting to external stakeholders, and owning commercial outcomes. You should bring a portfolio that demonstrates leadership, not just execution.

Key Responsibilities:

Design & Execution

• Lead the design and optimization of embedded insurance purchase flows, offer surfaces, sales panels, and product comparison experiences that drive attach rate and conversion within partner platforms

• Design clear information architecture for complex insurance journeys — structuring product options, coverage details, pricing, and legal disclosures so customers can make confident decisions quickly

• Apply strong interaction design craft to multi-step flows: progressive disclosure, smart defaults, inline validation, error recovery, and trust-building patterns (social proof, security signals, transparency cues)

• Map end-to-end user journeys across embedded contexts, identifying where insurance touch points sit within a partner's existing flow and designing seamless handoffs

• Design responsive, cross-platform experiences that perform across desktop, mobile web, and in-app webviews — accounting for the constraints of embedded iframes and partner viewport limitations

• Design insurance experiences for partner contexts — adapting UI solutions to align with diverse brand guidelines, platform constraints, regulatory requirements, and integration patterns

• Create high-fidelity prototypes and specifications that work within our design system while flexing to partner requirements and insurance product complexity

• Ensure accessibility standards (WCAG 2.1 AA minimum) are met across all insurance experiences, with particular attention to form design, error states, and screen reader compatibility

• Manage multiple concurrent projects across partner integrations while maintaining quality and momentum

• Collaborate with engineers to ensure high-quality implementation of insurance experiences across varying partner tech environments

Growth & Experimentation

• Define and create component variations and UI treatments for insurance offer surfaces, purpose-built for A/B testing and rapid experimentation across partner environments

• Translate growth hypotheses into testable design solutions in partnership with Product and Growth teams; advocate for design-led experimentation on insurance attach and conversion

• Identify and reduce friction across insurance product discovery, quoting, comparison, and checkout flows through data analysis and user research

• Own the design side of insurance conversion optimization including thinking in attach rates, quote-to-bind funnels, and revenue impact, not just usability

AI Augmented Design Practice

• Use generative AI tools (e.g., LLMs, image generators, code assistants) to accelerate prototyping, variant generation, copy exploration, and asset creation

• Apply AI-assisted research and synthesis workflows to rapidly distill user insights, competitive analysis, and data patterns into actionable design direction

• Integrate AI into experimentation workflows — generating test hypotheses, producing personalized content variants at scale, and analyzing experiment results faster

• Evaluate and introduce new AI tools, plugins, and workflows to the design team; build lightweight playbooks so others can adopt them

• Pioneer AI-native design methods (e.g., prompt-driven UI generation, AI-assisted design QA, automated accessibility checks) and document learnings for team-wide adoption

Research & Insights

• Plan, conduct, and facilitate generative and evaluative user research — from discovery interviews and journey mapping workshops to usability testing — to inform design direction and validate decisions

• Build repeatable testing practices within the domain, including lightweight unmoderated testing for rapid iteration cycles

• Leverage AI-powered synthesis tools to process qualitative and quantitative research data at speed, surfacing patterns that inform design decisions

• Partner with content designers to ensure insurance language, disclosures, and trust messaging are tested alongside UI patterns

Systems & Leadership

• Drive the evolution of our design system, building flexible, scalable components that perform across partner contexts and insurance product types

• Articulate design rationale clearly to internal teams and external partners, including presenting insurance experience designs directly to partner stakeholders

What you will bring:

• 8+ years of experience in product/UX design with a strong track record in ecommerce, marketplace, fintech, or conversion-focused digital products, not SaaS or enterprise platforms

• Proven growth design experience: A/B testing, funnel optimization, and experiment-led iteration with measurable commercial outcomes (attach rate, conversion, revenue). Case studies required, we want to see the numbers

• Strong UX fundamentals: information architecture, user journey mapping, interaction design, and form/flow design for complex multi-step transactional experiences

• Experience designing embedded or white-label experiences that integrate into third-party platforms, understanding the constraints of designing for someone else's brand context

• Deep interaction design skills: progressive disclosure, error handling, trust patterns, smart defaults, and edge case thinking for flows where clarity and confidence drive conversion

• Experience designing responsive experiences across desktop, mobile web, and in-app webviews — bonus if you've worked within embedded iframe or widget constraints

• Strong product discovery skills: identifying user needs, mapping competitive landscapes, and surfacing design opportunities

• Sharp attention to detail in visual design: micro-interactions, spacing, typography, and pixel-level craft matter to you

• Working knowledge of accessibility standards (WCAG 2.1 AA) and experience designing inclusive transactional experiences

• Proficiency in Figma, including interactive prototyping and working within design systems

• Familiarity with analytics platforms (e.g., GA4, Amplitude) and experimentation tools (e.g., Optimizely, LaunchDarkly) to inform and measure design impact

• Excellent communication skills: able to articulate design rationale to both internal stakeholders and external partners, with experience presenting to senior or external audiences

• Proven experience leading design workstreams within cross-functional teams spanning product, engineering, growth, marketing, and content — not just contributing

• Comfortable producing campaign and marketing design assets alongside core product work

AI Specific Requirements

• Demonstrated, active use of AI tools in your design workflow — not theoretical interest, but shipped work or documented process improvements. Show us in your portfolio or case study

• Experience using LLMs (e.g., Claude, ChatGPT, Copilot) for tasks like copy generation, UX writing variants, research synthesis, or design exploration

• Familiarity with AI-powered design and prototyping tools (e.g., Galileo AI, Figma AI features, Mid-journey/DALL-E for concept exploration)

• Experience or strong interest in using AI within experimentation workflows — generating test variants, personalizing content, or accelerating analysis

• Curiosity and initiative to evaluate emerging AI tools and introduce new workflows to the team

What you will have:

• A pixel-perfect eye for detail and a passion for data-informed design

• Deep UX craft: You sweat the details on form design, error states, loading patterns, and edge cases that most designers skip

• Strong visual and interaction design fundamentals with a portfolio that demonstrates both

• Systems thinker who can zoom from IA-level structure down to micro-interaction polish

• Proactive mindset with the ability to identify opportunities and drive solutions independently

• Exceptional time management and ability to prioritize multiple concurrent projects

• Comfortable working autonomously while collaborating effectively across multiple teams

• A/B testing mindset with experience designing experiments and measuring impact

• Demonstrated ability to mentor and elevate the work of other designers

• AI-native working style which defaults to using AI tools to accelerate and augment work rather than treating them as optional add-ons

• Willingness to experiment publicly, share AI learnings, and help the team build new muscle

• Growth-oriented commercial instinct: You think in attach rates, quote-to-bind funnels, and revenue impact, not just user satisfaction

• Bold, authentic and solutions-focused mindset aligned with CG's value

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.

• 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.

*The base salary range for this role is C$120,000 - C$150,000