Senior UX Designer (Contract, Remote First)

Posted Yesterday
Be an Early Applicant
Hiring Remotely in Toronto, ON, CAN
In-Office or Remote
95K-115K Annually
Senior level
Insurance
The Role
Lead end-to-end UX design for customer-facing and internal insurance applications, from research and discovery through prototyping, launch, and optimization. Simplify complex insurance workflows, create service blueprints, use analytics and A/B testing, collaborate with product and engineering teams, evolve the design system, ensure accessibility, and mentor junior and intermediate designers.
Summary Generated by Built In
About Us:
Zensurance is redefining commercial insurance for Canadian businesses. 
 
As a leading InsurTech, we make getting the right coverage simple, fast, and accessible through a digital-first experience. Our platform combines advanced technology with deep industry expertise to deliver tailored insurance solutions that help businesses thrive.
 
Zensurance has been recognized for its rapid growth and industry impact:
 
✅ Deloitte’s Technology Fast 50 (2023, 2024, 2025)
Deloitte’s Technology Fast 500 (2024, 2025)
Top Insurance Employers (2022)
 
At Zensurance, we value ownership, collaboration, and innovation. Our team thrives on solving complex challenges, challenging the status quo, and making a real impact in an industry ready for change. 
 
If you're looking to build something meaningful in a fast-growing, customer-focused company, we’d love to hear from you!

We're looking for a Senior UX Designer to join us for a 9-month contract.


As a Senior UX Designer, you will be the champion for our users—small business owners, brokers, and internal partners. You will lead the design strategy across our product domains, including both customer-facing and internal applications.

This role will take ownership of key product areas, contribute to the application-wide design system and guidelines, and seek to improve design processes and collaboration. 

Key Responsibilities:

  • End-to-End Ownership: Lead the design process from initial discovery and user research to high-fidelity prototyping and post-launch optimization.
  • Complex Problem Solving: Simplify intricate insurance logic into clear, accessible user journeys. You’ll create service blueprints that map out the entire lifecycle of a policy.

  • Data-Driven Iteration: Use product analytics and A/B testing results to validate your designs and drive conversion improvements.

  • Cross-Functional Leadership: Partner closely with Product Managers and Engineering Tech Leads to ensure technical feasibility and alignment on our product roadmap.

  • Design System Evolution: Contribute to and advocate for our internal design system to ensure consistency, accessibility (AODA/WCAG), and scalability across our platform.

  • Mentorship: Provide thoughtful feedback during design reviews and mentor intermediate/junior designers to help elevate the team’s collective craft.

  •  

Qualifications:

  • 5+ Years of Experience: Proven track record in UX/Product Design, ideally within Fintech, Insurtech, or complex SaaS environments.
  • Portfolio of Impact: A portfolio that showcases your thinking process—not just final screens. We want to see how you handled constraints and navigated complex user flows.

  • Tool Mastery: Expert-level skills in Figma and familiarity with modern hand-off and research tools.

  • Strategic Mindset: Ability to balance "blue-sky" vision with the "MVP" reality of an agile, fast-moving startup.

  • Communication: You can articulate the why behind your design decisions to stakeholders, turning data and research into compelling narratives.

Join Our Engineering Team - Where Growth Meets Innovation
 
At Zensurance, we believe engineering is more than just writing great code. It’s about learning, growing, and building something meaningful together. Our remote-first team is a place where you’ll be challenged, supported, and encouraged to thrive. Here’s what makes our team special:
 
✔ A Leadership Team That’s Got Your Back
Our experienced and approachable engineering leaders aren’t just here to manage - they’re here to mentor, guide, and help you unlock your full potential.
 
✔ Fuel Your Growth
We invest in your learning with training budgets, professional development programs, and mentorship opportunities. Want to explore a new tech stack or level up your skills? We can help get you there.
 
✔ A Culture of Sharing & Support
From Power-Ups and book clubs to tech talks and hackathons, we believe in learning from each other. Have a cool idea or an interesting challenge? Let’s solve it together.
 
✔  Hack, Build, and Innovate
Twice a year, we hit pause on our regular work for company-wide hackathons, giving you the chance to experiment, push boundaries, and build something awesome.
 
✔ Clear Career Growth, No Guesswork
We don’t do vague career paths. Our well-defined growth tracks show you exactly what’s needed to take your career to the next level, in a way that aligns with your skills and ambitions.
 
And the best part? You’ll work on exciting projects using cutting-edge technologies like TypeScript, NestJS microservices, and micro-frontends with React. If you're looking for a team that values learning, collaboration, and impactful work, we’d love to meet you!
 
Perks at Zensurance:
 
At Zensurance, we know that when our people thrive, so does our business. That’s why we offer a flexible, people-first work environment designed to support your well-being, growth, and success.
 
💻 Work Your Way
 
• Remote-first setup for added flexibility 
• Home office allowance to create a comfortable workspace
• Top-tier tech: "Office in a box" with all necessary tech equipment
• Half days before public holidays: Enjoy half days before long weekends
 
🤝 Staying Connected
 
• Weekly Friday huddles to share updates and connect across teams
• Virtual & in-person team-building events to strengthen our culture
 
We’re building something special. Come be a part of it!
 
Who We Are:
 
Business is hard work, but insurance doesn’t have to be!
 
We empower business owners with simple, tech-driven insurance solutions through our online platform. 
 
Our success is fueled by our team-oriented culture and four core values:
 
DELIVER – We set ambitious goals and achieve them.
INCLUDE – We foster an open and safe space for all.
INTEGRITY – We do what’s right.
INVENT – We create straightforward, innovative solutions.
 
AI Tools and Your Interview:
 
We know AI is a valuable tool, and you're welcome to use it to prepare for your interview. However, please don't use AI assistants during the live interview itself. We want to have an authentic conversation with you, and using AI during the interview could affect our evaluation of your suitability for the role.
 
Just so you know, we use an AI scribe to help us take notes and review interviews, ensuring a fair and clear process.
 
Diversity & Inclusion:
 
Zensurance celebrates diversity and is committed to creating an inclusive environment. We welcome applications from all backgrounds and provide accommodations throughout the hiring process. If you need support, let us know, we’re here to help.
 
Thank You!
 
We review every application with care to find the best fit for our team.
 
While we may take a little time to get back to you due to the high volume of applications we receive, know that a real human (not a bot!) is reviewing yours. We appreciate your patience and can't wait to learn more about you!

Skills Required

  • 5+ years of experience in UX or product design
  • Portfolio demonstrating design thinking, handling constraints, and navigating complex user flows
  • Expert-level proficiency in Figma
  • Familiarity with modern design handoff and user research tools
  • Ability to balance long-term vision with MVP delivery in an agile startup environment
  • Ability to communicate design rationale and translate data and research into stakeholder narratives
  • Experience in fintech, insurtech, or complex SaaS environments
Am I A Good Fit?
beta
Get Personalized Job Insights.
Our AI-powered fit analysis compares your resume with a job listing so you know if your skills & experience align.

The Company
HQ: Toronto, Ontario
232 Employees
Year Founded: 2016

What We Do

Zensurance is a Toronto-based technology company and leading source for small business insurance in Canada. We make it easy, quick, and affordable for startups, self-employed professionals, contractors, and small businesses to get insured. Through our highly regarded client support team and network of over 50 insurance providers, Zensurance provides customers with industry-leading premium savings and the confidence to thrive in today’s market. #Zensurance #WeAreZensurance

Similar Jobs

Block Logo Block

Software Engineer

Blockchain • eCommerce • Fintech • Payments • Software • Financial Services • Cryptocurrency
In-Office or Remote
8 Locations
12000 Employees
264K-395K Annually

Cash App Logo Cash App

Software Engineer

Blockchain • Fintech • Mobile • Payments • Software • Financial Services
Remote or Hybrid
8 Locations
3500 Employees
264K-395K Annually

Zapier Logo Zapier

Automation Strategist, Customer Success

Artificial Intelligence • Productivity • Software • Automation
In-Office or Remote
3 Locations
800 Employees
158K-238K Annually

CrowdStrike Logo CrowdStrike

Consultant

Cloud • Computer Vision • Information Technology • Sales • Security • Cybersecurity
Remote or Hybrid
6 Locations
11000 Employees
90K-135K Annually

Similar Companies Hiring

MassMutual India Thumbnail
Big Data • Fintech • Information Technology • Insurance • Financial Services
Hyderabad, Telangana
Granted Thumbnail
Artificial Intelligence • Healthtech • Insurance • Mobile • Financial Services
New York, New York
23 Employees
Vega Thumbnail
Artificial Intelligence • Automotive • Insurance • Transportation
US
43 Employees

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account