Insuring Growth

Designing Insurance zero to one

DESIGN THINKING. STRATEGY. RESEARCH. TESTING. DESIGN SYSTEM

SUMMARY

Executive Snapshot

Situation

Questrade aimed to launch its first home and auto insurance offering in the highly competitive $57 billion Canadian P&C market.

The challenge was that most digital insurance journeys in Canada were complex, filled with jargon, and led to over 60% of users abandoning their quotes. Meanwhile, brokers faced difficulties due to fragmented tools and excessive manual work, undermining efficiency and the customer experience.

My Role

As Lead Product Designer and Manager, I owned the end-to-end design strategy for the insurance initiative. I managed a team of four designers and partnered with one Discovery squad and two cross-functional Delivery squads (Product Owners, Engineers, QA, brokers, and compliance) to build the platform from the ground up.

Actions and Outcomes

Reduced cognitive load and friction throughout all journeys by redesigning the quote-to-bind flow and policy management, leading to 10,311 projected first-year policies sold (2025–2026) and a significant increase in the overall conversion rate.
Facilitated cross-sell integration within the customer portal, enabling targeted insurance offers for Questrade’s existing customer base, contributing to a projected cumulative revenue of $208M and projected gross written premiums of $450M from 2025 to 2030.
Optimized agent workflows and automated low-value tasks, which reduced agent SLAs for both sales and service teams by 25%, significantly enhancing operational efficiency.
Leveraged and expanded Questrade’s design system with insurance-specific components, accelerating time to market and reducing the iteration/testing period by 30%. This also enhanced engineering hand-off efficiency by 40%, facilitating smoother collaboration and faster releases.

BACKGROUND AND CONTEXT

Disruption in a stagnant industry

Questrade, a leader in digital investing, aimed to introduce its first home and auto insurance product in Canada, a $57 billion market historically marked by complexity, poor user experiences, and outdated legacy platforms.

Recognizing the pain points (high abandonment rates, manual broker inefficiencies, and unclear digital journeys), Questrade’s mission was to provide a unified, seamless experience that could attract both new and existing customers. This case study illustrates how a design-led approach facilitated rapid market entry, cross-sell synergies, and a measurable business impact.

Our North Star Revolutionizes insurance for Canadians by providing the easiest and most flexible experience through an advice-based, humanized digital journey using simple language that makes them feel confident they have the coverage they need at a price they can afford.

CONSUMER PERSPECTIVE

Problem space and Opportunity

Make Insurance Easy to Buy

Consumer Behavior

70% of shoppers start their journey digitally, yet most insurance journeys feel outdated, jargon-heavy and disjointed.

Insight

Consumers optimize for price because they assume they’ll never use the product not because it's what they want, but because they don’t trust the value.

Opportunity

Build a digital-first experience that uses Questrade’s trusted brand to make insurance feel clear, trustworthy, and simple to act on.

Empower Smart Customization

Consumer Need

60% of Canadians want the ability to adjust coverage in real-time based on needs and budget.

Insight

People are willing to pay more if they understand what they’re getting. But most quoting tools feel like black boxes.

Opportunity

Build an interactive coverage selector that shows the real-time price trade-offs for informed decision-making.

Build Trust Through Claims

Consumer Behavior

Half of buyers investigate claims experience before purchase but 35% of users who actually make a claim find it confusing and judgmental.

Opportunity

Design a self-serve and transparent claims experience that prioritizes empathy.

Empower Agents with Better Tools

Insight

Agents spend 65 % of their time on fragmented admin tools, limiting high-value advising.

Opportunity

Automate manual workflows and enhance the overall experience, allowing agents to focus on building strong client relationships.

TARGET AUDIENCE

Segmentation and Cohort

The key target cohorts we focused on were Innovative and Price-First mindsets, which make up 36% of the total addressable market.

They have also demonstrated the greatest likelihood of switching to providers, as they have the least attachment to their current insurer.
There is a considerable likelihood that individuals will utilise digital self-help resources first when faced with insurance-related questions and making digital purchases.
There is an overlap with over 80% of Questrade's investment users who fall into one of the “price first” segments.

The mindset approach allows us to comprehend the insurance landscape, identify key segments grounded in market realities, and enable us to succeed in both the short and long term as we scale and become a significant player in the Canadian insurance landscape.

PROCESS

Mapping the Journeys

We synthesized the Discovery and market research sessions into journey maps to identify moments of friction and opportunity across the quote-to-renewal lifecycle.

01.

Pre-Awareness & Awareness

Customers rely significantly on family, friends, and personal networks for their initial research.
There is uncertainty regarding the type of insurance required and whom to trust.
They seek clear and educational content to build confidence in their early decisions.

02.

Consideration

Customers feel overwhelmed by confusing quotes, jargon, and unclear trade-offs. A lack of personalized help is a common pain point; many wish a broker or agent would “just tell them what’s best.”

03.

Purchase

Frustrations peak because of the repetition of information, unclear pricing, and a lack of clarity regarding what is included or excluded.
Customers expect fast, seamless digital quoting but often encounter slowdowns or friction.

04.

Renewal

At this stage, many individuals are indifferent and typically switch only when prompted by a significant event or a price increase.
Customers prefer to be proactively informed about changes rather than simply reminded to renew.

PROCESS

Studying the competitor landscape

I categorized our competitors in the Home and Auto insurance sector into two groups: Direct and Challengers. GenAI has been particularly useful in this research, serving as an initial turbocharger to not only identify challengers outside the North American market but also to summarize insights, conduct SWOT analyses, and perform a gap analysis comparing them to competitors.

I took that initial research and analyzed the detailed journey based on:

Quote Initiation and Data Collection

How many fields before showing a price? How does Pre-fill data work, and what information is being pre-filled?

Coverage and Pricing

How are different coverages explained? Are exclusions buried? How are price impacts and changes communicated?

Post-Purchase experience

Policy management and overall self-serve experience.

Omini-Channel

Are customers able to start online and complete the process with a broker without having to repeat information? What channels do they use?

EXPERIENCE PRINCIPLES

Consistency and clarity with principles

Establishing guiding principles acts as a North Star throughout the design process. They ensure that every feature, interaction, and interface choice consistently addresses core user needs and aligns with the underlying business outcomes.

Principles

Transparency, Hassle-Free Experience, Personalization, Value, Proactivity and Flexibility.

PROCESS

Design through ideations and testing

After gathering insights from the empathy and discovery interviews, journey mapping exercise, and competitor analysis, we started brainstorming concepts for the quote and bind experience.

I used Questrade’s design system to create three versions (short, medium, long) of the experience, which were then tested on the grounds of speed v/s accuracy while balancing simplicity and value creation.

Test 1 method

Moderated interviews with a total of 11 interviews.

Insights

There was no strong preference for speed over accuracy or vice versa. Reactions for the initial quick quote/price in the short flow were polarized.
No difference of opinion were founds between the two target cohorts.
Unsatisfactory evidence to prove that the medium flow was preferred over the short.

Unfortunately, The results weren't conclusive enough to choose one flow over the other. This meant we had to go back to the drawing board. We conducted a detailed analysis of all the fields required for obtaining a quote as well as binding a policy, narrowing it down to only those fields that impact pricing and eligibility.

Working through the ideations and design, we conducted additional tests for the Auto and Home flows, both on Desktop and mobile, based on the insights and findings from the previous test, stakeholder feedback, and internal playback sessions.

Test 2 and 3 method

Moderated usability tests with 8 interviews each (Home and Auto).

Insights

Education through the pre and post-quoting experience was critical, leading to transparency and trust.
Providing personal information, such as a driver's license, VIN, or home address, that resulted in data being pre-filled came with the expectation of generating a more accurate quote.
Details regarding individual coverages, inclusions, and exclusions in your policy offered a greater understanding of what was being purchased.
Seeing individual monthly costs per coverage, having the ability to customize them, and understanding their impact on price facilitated easier decision-making.

Simultaneously, I ran design workshops to explore what a Self-serve customer portal could potentially contain, aligning with the pain points we uncovered for consumers. With the help of our Research team, conducted usuability test on the customer portal to uncover alignment with expectations and need.

Test 4 method

Moderated test with 11 interviews

Insights

Providing a simple structure for policy details made it easy to understand.
Access to old policy data was useful especially when switching or comparing while shopping around for another insurer.
The claims process was considered a crucial part of their self-serve experience, typically with access to help either digital or in-person on demand.

OPPOSITE SIDE OF THE COIN

Understanding agent workflows

In 2022, Questrade acquired an insurance brokerage to gain market exposure. We initially leveraged the broker’s existing tools for Questrade Insurance. Once we reviewed workflows, tools, and processes, we spotted many redundancies, brokers were spending excessive time on low-value work like document uploads and switching between systems, which hurt SLAs and strained client relationships.

I conducted shadow sessions with sales and service brokers to better understand their pain points and identify optimization opportunities. Meanwhile, the design team began revamping the legacy platform into a version 1 broker test release.

Common pain points in the current Sales and Service workflows

Extreme Cognitive Overload

Brokers must remember where to find each piece of data, slowing them down and increasing errors. Heavy training is required, with a risk of mis-keying, and there is no inline help or tooltips to explain the jargon.

Poor Information Hierarchy

Critical, time-sensitive information gets lost in the noise.

Manual, Multi-Step Upload Process

Context-switching and repeated clicks add minutes per policy and frustrate brokers.

SOLUTIONS

Make Insurance Easy to Buy

Based on the insights from our testing and design iteration rounds, we decoupled the purchasing experience into pre- and post-quote phases, which simplified the overall journey, allowing users to focus on one decision at a time and see real-time pricing impacts.

By integrating OCR-powered license scanning, we eliminated 80 % of manual data entry fields. While using a mobile device, users can even snap a photo of their driver’s license within a few seconds. The system auto-populates drivers, vehicles and history, cutting the average quote-start time from 4 minutes to under a minute.

Unfortunately, we were unable to implement an API service (OPTA) for the home insurance experience due to cost, but we were able to take a balanced approach between gathering information from users and making assumptions based on the field framework.

SOLUTIONS

Empower Smart Customization

We built collapsible ‘Coverage Cards’ for each policy element (liability, collision, comprehensive). Each element displays an individual price, a tooltip and a dynamic limit adjuster. As users adjust their deductible or sub-limit, the monthly premium updates in real-time, empowering informed trade-off decisions.

The Digital Advice Center (DAC) provides personalized recommendations based on user profile and risk tolerance (e.g., suggesting 'Sewer Backup' if a user’s ZIP code indicates a high flood incidence). We used an AI engine tied to the claims data to generate these contextually relevant tips at each step.

With the help of guided bottom sheets and interactive alerts on the screen, users are able to understand coverage details and changes that are happening to their coverage as well as justify trade-offs while making decisions easier to take.

SOLUTIONS

Build Trust Through Claims

We designed a unified portal allowing users to view active and expired policies, access documents, submit change requests and initiate claims. Implemented features like ‘Schedule a call’ that allows the agents to call back customers at their preferred time.

Policy details for home and auto helps customer get access to all their documents as well as allows to request any changes to the policy or coverages.

We made it seamless for an existing Questrade customer to now utilize the customer portal and sign-up for insurance products.

SOLUTIONS

Empower Agents with Better Tools

We streamlined the platform pages, search, and dynamic forms to reduce average policy entry time by up to 30%, allowing agents to quote and bind more business.

Real-time validation and contextual guidance help reduce manual correction cycles by 20%, saving on compliance and support overhead. With agents freed to focus on consultative selling rather than data entry, we can expect a 10-15% increase in cross-selling and renewal rates.

WHAT'S NEXT

Journey post launch

Post-launch, our design roadmap centers on three pillars: Optimize, Expand and Scale. First, we'll continuously monitor support metrics to identify high-impact tweaks, fine-tuning our quote-to-bind flows, error states, and microcopy via rapid A/B tests.

Next, we'll roll out Phase 2 features, including AI-driven coverage recommendations, enhanced OCR scanning for other areas of the purchasing experience, and a proactive notifications hub prioritized based on direct feedback.

Finally, we'll deepen platform reach by extending insurance-specific components into new verticals (commercial) and embedding our design system into Questrade's native mobile app, all while maintaining our bi-weekly design reviews to keep alignment with Product, Engineering and leadership.