Staff Product Designer - Insurance

About The RoleHello! I’m Colin, the Senior Design Manager at Jane. Having been part of this remarkable team for over two years, I have the privilege of collaborating with a dedicated group of designers who are passionate about crafting intuitive and enjoyable experiences. Our Design team is committed to empowering practitioners to focus on their true calling - serving their clients - by alleviating obstacles and simplifying complex tasks.On a personal note, I reside on BC’s upper Sunshine Coast. When I’m not immersed in design, I enjoy biking, creating experimental music, playing tabletop games, or diving into small-press comics.We are seeking a Staff Product Designer for our Insurance team. This team is pivotal in shaping and executing Jane’s long-term strategy to support practitioners in setting up, managing, and processing insurance claims for their clients. Insurance billing is crucial for the success of clinics, yet it often comes with challenges. We believe in enhancing this process, and your contributions will help transform how thousands of clinics manage payments, serve patients, and expand their businesses.This role is particularly exciting as it merges significant customer impact with intricate problem-solving and robust design leadership. You will play a vital role in transitioning from merely delivering features to addressing the core issues, while designing an insurance experience that feels trustworthy, human, and genuinely beneficial.What Impact We’re Looking for You to MakeDesign insurance billing experiences that are efficient, transparent, and as hassle-free as possible for both clinics and patients, ensuring prompt and confident payments.Champion our customers by anchoring decisions in thoughtful user research, clearly articulating their needs, and keeping teams focused on actual problems.Embrace leadership opportunities by aligning stakeholders, communicating the rationale behind your work with clarity, and utilizing storytelling to engage cross-functional partners.Elevate design quality by consistently delivering strong outcomes, iterating based on real-world feedback, and creating experiences that foster trust and delight over time.Transform vague and abstract challenges into concrete, well-defined solutions that guide teams from feature-centric execution to genuine problem-solving.

This is a fully remote position available to candidates across Canada.At Jobber, we empower small businesses to thrive by revolutionizing how they deliver services through innovative technology. Our platform enables home service professionals—such as plumbers, electricians, painters, and landscapers—to efficiently quote, schedule, invoice, and collect payments, all while enhancing their customer experience. As the landscape of service delivery evolves, we equip small businesses with the flexibility and tools they need to succeed in a digital age.Recognized for our commitment to transparency, inclusivity, collaboration, and innovation, Jobber has been honored by Great Place to Work and featured in Canada’s Most Admired Corporate Cultures. We are also proud to be listed among the Globe and Mail’s Canada’s Top Growing Companies and Deloitte Canada’s Technology Fast 50™, Enterprise Fast 15, and Technology Fast 500™. Since our inception in 2011, our executive team—boasting over thirty years of combined industry experience—has been dedicated to enhancing our offerings for our customers, and we are just getting started for our customers.Your Role:As a key member of our Product Design team, you will transform conceptual ideas into engaging user experiences. By harmonizing user interface (UI), user experience (UX), research, and content design, you will address user and business challenges, creating polished and impactful interfaces. You will work under the guidance of a Design Manager dedicated to fostering your growth and skill development.In this role, you will be part of our vital Fintech team, which focuses on empowering small business owners by providing them with tools to understand, manage, and optimize their financial standing. By offering insights and seamless financial solutions, our aim is to deliver effortless experiences tailored to our customers' needs. As the lead designer within the Fintech group, you will collaborate with cross-functional teams to drive strategy and uphold the quality of our product design.Join Our Team:As a vital contributor to the broader Product Development team, you will collaborate closely with Product Managers and Engineers to achieve our business objectives and enhance our customers' experiences.

Location: North America (Canada or US), Remote Narvar is on a remarkable growth trajectory! We are seeking a highly skilled Staff Product Designer to assume a crucial leadership position within one of our key product pillars. This is a distinctive chance to tackle intricate, high-stakes challenges and reshape the essential experiences that fuel Narvar's success for some of the world's most cherished brands. In the role of Staff Product Designer, you will serve as a strategic design partner, accountable for enhancing the user experience across a suite of products that cater to both retailers and their end customers. Your contributions will be vital in transforming multifaceted challenges into straightforward, guided, and intelligent solutions. Day-to-day Responsibilities Drive the UX vision and strategy for your designated product pillar, crafting seamless and interconnected experiences for both retailers (merchants) and their end customers (consumers). Design for intricate systems: Address ambiguous problem spaces and lead design efforts for sophisticated workflows, configuration tools, and data-rich interfaces that are both powerful and user-friendly. Deep collaboration: Engage closely with product managers and engineering leads to translate complex business needs into elegant and effective design solutions. Mentor and elevate: Act as a guiding figure and mentor within the design team, enhancing the craft, refining our processes, and fostering the growth of junior talent. Communicate effectively: Clearly express your design rationale and vision to stakeholders at all levels, from your immediate team to the executive leadership. Champion a robust foundation: Collaborate with peers to establish and refine a scalable information architecture and consistent interaction models for the future of the Narvar platform. What We Are Seeking 7+ years of experience in product design, showcasing a robust portfolio that highlights your work on complex B2B SaaS applications, enterprise tools, consumer-facing applications, and your ability to lead projects from concept through to launch. Strategic product thinker: You possess a passion for understanding the rationale behind your work and can effectively partner with product management to define the product vision, beyond just executing features. Systems thinker: You have demonstrated experience in untangling complex, fragmented systems and designing logical, user-centric solutions. Proficient in design tools: Expertise in using design tools such as Sketch, Figma, or Adobe Creative Suite to create high-fidelity prototypes. Excellent communication skills: Ability to articulate design concepts and collaborate well with cross-functional teams.

We are seeking a talented and innovative Staff Product Designer to join our team at GitLab. In this role, you will play a pivotal part in shaping our Knowledge Graph product, collaborating closely with cross-functional teams to enhance user experience and drive product evolution.Your responsibilities will include conducting user research, creating wireframes, prototypes, and high-fidelity designs, as well as advocating for user-centered design principles throughout the development process. If you are passionate about crafting intuitive and impactful designs that improve user engagement, we want to hear from you!

Affirm, Inc. seeks a Staff Product Designer to influence the direction of financial technology products. This fully remote position is open to candidates living anywhere in Canada. Key responsibilities Create user experiences that help people make better financial decisions Collaborate with teams across disciplines to develop and refine Affirm’s products Offer design ideas that align with Affirm’s goal of making finance more accessible Location This role is remote and available to applicants based in Canada.

Join Jobber as a Staff Product Designer, Sales and play a pivotal role in shaping user experiences for our sales platform. Collaborate with cross-functional teams to design innovative solutions that drive customer engagement and satisfaction. You will be responsible for creating user-centered designs, conducting user research, and iterating on designs based on feedback and testing.

Be a Part of Our Innovative Design TeamAt Planera, a dynamic Series A Construction Scheduling Startup, we are on a mission to revolutionize one of the most significant industries globally. Our products are setting new standards for how General Contractors and their teams create world-class construction schedules. This is a unique opportunity to establish the design vision at a rapidly scaling organization, supported by the resources of a well-funded startup and energized by a fast-paced environment.We are seeking a Staff Product Designer with a keen emphasis on mobile application design to help shape and deliver Planera’s mobile experience. This position is for a senior individual contributor who can navigate complex problem spaces, spearhead impactful initiatives, and enhance mobile design in new product experiences.You will collaborate closely with product managers, engineers, and company leadership to translate real-world construction scheduling workflows into intuitive, high-quality mobile experiences that are utilized daily in the field. This role is perfectly suited for someone who thrives in uncertain environments, pays attention to interaction details, and can think strategically about systems and products.If you are passionate about crafting elegant product experiences that have a tangible impact on the real world—and you want to leave your mark on the future of construction—this is your platform.

POS-29684Location: Ontario, Canada - Remote, Flexible, or OfficeJoin HubSpot’s Innovative Design TeamAt HubSpot, we are on a mission to accelerate our growth by leveraging AI to transform how we support our customers and empower our Go-to-Market (GTM) teams. The Flywheel Product Line is at the forefront of this initiative, focusing on three key areas:AI Concierge Development: We're creating an AI-powered concierge that enhances the customer journey by autonomously addressing support issues, uncovering goals, and maximizing the value customers derive from HubSpot. This involves sophisticated design challenges across various modalities, including chat, voice, and AI-generated video.AI-First Tools for GTM Teams: We're revolutionizing the efficiency of our support, sales, and customer success teams by streamlining administrative tasks and empowering managers with advanced coaching capabilities. These enhancements are designed to significantly boost revenue and optimize performance.Partner Ecosystem Experiences: We are dedicated to enhancing the experiences of our global partner network, which generates over $1B in revenue annually. By developing tailored AI solutions and unique tools, we aim to help our partners thrive and contribute to HubSpot's ongoing success.As a Senior Product Designer, you will not be confined to one team or feature. Instead, you'll have the opportunity to influence the product line direction across diverse domains. Your work will span 3-12 months ahead of delivery, engaging in exploratory design, prototyping innovative concepts, and crafting narratives that will shape decision-making across R&D and GTM teams.This role is centered around strategic vision and impactful influence, pushing the boundaries of applied AI to define the future for a company valued over $30 billion.Why Choose Flywheel?Join us for a transformative career opportunity where you can:

Discover OktaAt Okta, we are redefining identity management, empowering individuals to securely access technology on any device and application. Our innovative solutions, including the Okta and Auth0 platforms, are designed to provide robust security, authentication, and automation, placing identity at the forefront of business growth and protection.We value diversity and are committed to creating an inclusive environment. We seek passionate and curious individuals who are eager to contribute their unique perspectives and experiences to our team.Join us in our mission to make identity a personal asset.The Design TeamOur design team operates in a collaborative, distributed environment where we prioritize early sharing of work and constructive feedback. We are detail-oriented yet focused on continuous progress and learning.As a designer at Okta, you will have significant ownership over your work. You will collaborate with engineering and product management to influence product directions and create user experiences that impact millions globally.Your role will involve refining existing user flows and conceptualizing the future of identity and developer tools. We leverage asynchronous tools like Loom and Figma comments to maintain connectivity across time zones, and we foster an environment that encourages experimentation and personal growth. At the Staff level, you will also mentor fellow designers and establish best practices that elevate our entire team.The OpportunityJoin our Emerging Products team at Auth0, where we are dedicated to pioneering the next generation of identity and security solutions. We transform innovative concepts in areas such as AI, fine-grained authorization, and developer experience into tangible products ready for our customers.Our current projects include:AI + Identity: Enhancing AI assistants with identity-aware authorization.Cross-App Access: Creating seamless, policy-driven interactions between applications and user accounts.

Join Us in Revolutionizing Grocery Shopping!At Instacart, we are on a mission to make food accessible for everyone, allowing people to share love through meals. We recognize that grocery delivery is more than just convenience; it’s about meeting the diverse needs of our community. Our platform provides a vital service that countless customers depend on for their groceries and household essentials, while also creating flexible earning opportunities for our Personal Shoppers.As Instacart continues to serve as a lifeline for millions, we are expanding our team to drive our shopping cart forward. If you are eager to make a significant impact and do the best work of your life, we invite you to join us!Flexibility is Key at Instacart!We believe that there is no single way to achieve excellence. Our team members have the freedom to choose their ideal workspace—whether that’s at home, in an office, or at their favorite coffee shop—while fostering connections through regular in-person events. Discover more about our flexible work approach.ROLE OVERVIEWEvery year, people worldwide spend nearly one trillion dollars on groceries. This timeless industry is not just about sustenance; it embodies daily rituals, cherished memories, and shared moments. Food should always be easily accessible, whether for a special occasion or a regular meal.The Instacart Design Team is committed to transforming grocery shopping into a seamless experience for all, tackling large-scale challenges that will redefine how individuals nourish themselves and their loved ones. Our design efforts cater to a four-sided marketplace, addressing the needs of Consumers, Shoppers, Retailers, and Advertisers.We are currently seeking a Staff Product Designer to join our Lifecycle & Growth team. In this role, you will lead the design of experiences across Instacart’s subscription and growth ecosystem, shaping how users first discover, evaluate, and commit to our platform.

Shakepay seeks a Senior Staff Product Designer to help define the future of Bitcoin financial services for Canadians. This remote position is open to candidates living anywhere in Canada. Founded in 2015, Shakepay makes it easier for Canadians to buy, earn, and use Bitcoin. With the Shakepay Card, launched in 2022, users can earn Bitcoin rewards on daily purchases. Over one million Canadians trust Shakepay to manage their Bitcoin savings. The company operates under full regulation across Canada and has secured $44M in funding from top venture capital firms. Role overview This Senior Staff Product Designer will set the design strategy for important product areas and take on the most challenging design problems at Shakepay. The role focuses on raising the standard for design quality, influencing the direction of products, and supporting teams in delivering strong outcomes. Collaboration with Product and Engineering leadership is central, with an emphasis on building seamless, high-quality user experiences at scale. What you will do Lead high-impact projects: Take ownership of complex product challenges, turning ambiguous problems into clear, actionable solutions from beginning to end. Shape product and design direction: Work closely with Product and Engineering to influence the roadmap and ensure teams focus on the most important problems. Design for results: Craft user experiences that improve key metrics such as activation, engagement, retention, and conversion while maintaining high standards. Work across teams: Collaborate with multiple departments and product areas to deliver a consistent experience across the platform. Advance design systems: Build and evolve scalable design systems and patterns to boost quality and efficiency.

Shakepay creates financial tools that help Canadians access and benefit from Bitcoin. The mission centers on making Bitcoin simple, secure, and rewarding for people across Canada. Founded in 2015, Shakepay offers a platform for Canadians to buy, earn, and save Bitcoin. In 2022, the company launched the Shakepay Card, allowing users to earn Bitcoin rewards on everyday purchases. Today, over a million Canadians use Shakepay to build their Bitcoin savings and manage their finances. Shakepay operates under regulation in every Canadian province and territory. Backed by $44 million in funding from well-known investors, the company continues to grow and foster a strong community. Culture and work style Shakepay values meaningful work, collaboration, and celebrating team achievements. The group works quickly and encourages open sharing of ideas. Growth and timely delivery matter here, and those who appreciate teamwork and a fast-moving environment will likely thrive.

Shop Builder provides game developers with a no-code and low-code platform for building branded web stores. Teams can quickly launch stores to sell virtual goods, currencies, and subscriptions directly to players. By connecting an App Store or Google Play URL, developers enable the platform to generate a store that matches their game's branding within minutes. Shop Builder supports desktop, mobile browsers, and Progressive Web App (PWA) formats. Role overview Xsolla is seeking a Senior Staff Product Designer located in Canada to lead UX architecture and strategy for Shop Builder. This position shapes the product's direction and works closely with engineers throughout the development process, moving beyond traditional design handoffs. What you will do Guide the overall user experience and strategic direction for Shop Builder Collaborate directly with engineering teams to ensure seamless integration of design and technical requirements Engage deeply with technical details, including reading pull requests and using Git Requirements Experience leading UX architecture and product strategy Ability to communicate clearly and work closely with engineers Comfort with technical tools such as Git and reviewing pull requests Strong motivation to drive product innovation Based in Canada

As a Lead Product Designer at Alpaca, you will spearhead our design initiatives, creating user-centered solutions that impact our diverse customer base. You will collaborate closely with cross-functional teams, guiding the design process from concept to execution. Your expertise will help shape our product strategy and elevate the user experience across our platforms.

Role Overview Affinity is looking for a Senior Product Designer based in Canada (remote) to help turn complex ideas into clear, engaging designs. This role works closely with product, engineering, and other teams to understand user needs and create solutions that improve the experience across the Affinity platform. What You Will Do Partner with cross-functional teams to identify and address user needs Design intuitive, visually appealing interfaces that support product goals Apply design thinking and user-centered methods throughout the product development process Contribute to product strategy by shaping how users interact with the platform What We Value Strong creativity and a keen eye for detail Collaboration across teams and disciplines Commitment to design excellence and user-focused solutions

Join Us in Empowering Employees:At ZayZoon, our mission is to empower 10 million dedicated employees to save $10 billion. We have developed a cutting-edge financial empowerment platform designed to enhance employee financial wellness across businesses of all sizes.Our suite of financial wellness services includes earned wage access, allowing employees to access their earned wages before payday. With 74% of our customers reporting decreased financial stress, we are proud to contribute to happier, more productive workplaces. ZayZoon has been recognized for its rapid growth in the 2025 Deloitte Technology Fast 50, 2025 Deloitte Technology Fast 500, and as one of the top-10 growth companies in Canada by CIX awards. Our recent funding round has successfully raised nearly $50 million USD . Be part of our journey in revolutionizing employee financial wellness and developing solutions that meet the immediate needs of today’s workforce.While we list various locations, there’s no need to worry about being based in any specific city! We are fully remote and welcome applicants from across Canada and the U.S.About the Role:As the Director of Product Design at ZayZoon, you will lead and nurture our Product Design team while remaining hands-on in creating impactful, user-centered experiences that empower individuals to access their earnings confidently. Collaborating closely with Product, Engineering, Data, and Product Marketing, you will oversee the entire design process—from initial discovery and research to refined user interfaces—while developing scalable systems and workflows that facilitate rapid yet thoughtful progress. This role uniquely combines strong leadership with deep design expertise, advocating for user empathy, experimentation, and ongoing enhancement as we expand products that genuinely enhance lives. You will have meaningful ownership and the opportunity to make a significant difference.

Luxury Presence is on a mission to redefine growth for real estate professionals through innovative AI-driven solutions. As a Series C company backed by Bessemer Venture Partners and top-tier investors, we are poised to reach $100M in annual recurring revenue within the next six months. Currently, over 87,000 real estate professionals, including more than 30% of the WSJ Real Trends top 100 agents in the U.S., trust our platform to enhance their business operations. **Design at Luxury Presence** is pivotal to our vision of empowering real estate entrepreneurs with distinguished, user-centered digital experiences. We empower our designers with ownership and encourage them to challenge the status quo while driving both craft and strategy forward. We believe that exceptional design is rooted in empathy—it's functional, resilient, and developed from a thorough understanding of genuine customer needs. Our best work begins with curiosity about our users, their objectives, and the friction points that impede their progress. The role of design is to translate these insights into intuitive, elegant, and effective user experiences. Moreover, we uphold a high standard for visual quality. We recognize that strong craftsmanship builds trust, conveys care, and fosters delight. Our designers expertly balance usability with aesthetics to create product experiences that genuinely serve our users. Regardless of whether your passion lies in system design, product strategy, or mentoring teams, we collaborate with you to elevate our standards and create a lasting impact.

Join Upwork, the premier global marketplace that integrates human talent with AI capabilities to connect businesses with top-tier independent professionals worldwide. With a mission to facilitate growth and transformation, Upwork empowers companies from startups to Fortune 100 firms to harness over 10,000 skills across vital domains such as AI & machine learning, software development, marketing, customer support, and finance.As a leader in the industry, Upwork has created more than $25 billion in economic opportunities for talent around the globe. Explore more at Upwork.com and connect with us on LinkedIn, Facebook, Instagram, TikTok, and X.We are seeking a Lead Product Designer to enhance our Growth & Monetization team. This team focuses on translating customer value into sustainable revenue through fees, advertising, pricing strategies, and promotions.In this role, you will design and optimize impactful growth mechanisms and monetization features within our two-sided marketplace. Your work will emphasize user acquisition and retention, collaborating closely with Product, Data Science, Engineering, Marketing, and Research teams to implement experiments and enhance pricing and packaging experiences that are transparent and motivating for our customers.

At Hiive, we are transforming the way private companies and their shareholders access liquidity. Our institutional-grade platform connects buyers, sellers, and issuers to streamline secondary transactions in venture-backed, pre-IPO companies. We prioritize efficiency, transparency, and standardization in a traditionally opaque asset class.Recognized as one of Canada’s fastest-growing companies and supported by prominent U.S. investors, Hiive is not only profitable but also well-capitalized. We are actively building a high-performance team to meet increasing demand and explore new market opportunities.Curious about life at Hiive? Visit our careers page to discover how you can grow with us!As a Senior Product Designer at Hiive, you will be part of a dynamic, high-impact product team. You'll collaborate with talented Design, Product, and Engineering partners within a modern tech stack. We're seeking a fast learner who excels in cross-functional collaboration and can contribute to meaningful, measurable outcomes for our business.Your responsibilities will include:Leading the design of key product features and initiatives, from initial concept through to high-fidelity execution.Collaborating with cross-functional teams, including product managers, engineers, and fellow designers, to define product requirements and craft solutions that satisfy user needs and align with business objectives.Creating and maintaining a cohesive, scalable design system to ensure consistency across products and platforms.Conducting user research, usability testing, and gathering feedback to iteratively enhance design solutions.Designing for both web and mobile platforms, focusing on creating intuitive and delightful user experiences across devices.Owning and evolving the visual and interaction design of the product, ensuring high-quality, pixel-perfect designs.Leading design reviews and effectively presenting design concepts to stakeholders throughout the company.Supporting team members and championing company values with a positive and proactive attitude.Responding respectfully and effectively to diverse working conditions with a growth mindset.

Shakepay Inc. seeks a Senior Product Designer to influence the direction of its digital products. This is a remote role available to candidates living in Canada. Key responsibilities Create user-centered designs that enhance the customer experience and foster engagement Partner with teams across Shakepay to develop, iterate, and refine product concepts Deliver design work that meets high standards for consistency and quality Collaboration Expect to work closely with colleagues from different disciplines, helping turn ideas into features while ensuring the product remains cohesive and intuitive.