Conquest Planning is a leading financial planning software company with a purpose-driven approach to delivering financial advice. Established in 2018, Conquest Planning was founded by a team of financial technology veterans whose track record of success spans over 30 years in the financial planning software space. The company’s mission is to ensure that everyone has access to great financial advice, transforming the financial planning landscape and improving outcomes for all clients. Users of Conquest Planning leverage its intuitively designed product, simple onboarding process, and data-driven artificial intelligence to accelerate the delivery of beautifully designed, hyper-personalized financial plans. We are based out of Winnipeg, Manitoba and have team members located across Canada, the United States, and United Kingdom.

We are seeking a Product Designer – 1 Year Term to join our dynamic team! Ideally, the term will be until March 2027.  

As a Product Designer at Conquest Planning, you’ll own meaningful product areas end-to-end – taking complex financial concepts and turning them into clear, confident user experiences. You will work across discovery, definition, design, and delivery, using research, analytics, and strong systems thinking to guide decisions. You will collaborate closely with the Product and Development teams, and help elevate our design practices and design system as we scale.

This role is ideal for a designer who can balance high craft with pragmatic execution, and who thrives in a product environment where evidence, iteration, and cross-functional alignment matter.

This is a remote / work from home opportunity.
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Duties of the role include:  

Product Design Delivery

• Own features and workflows from early discovery through shipped UI, including interaction design, visual design, and content-level clarity.
• Translate ambiguous problem spaces into structured opportunities, user journeys, and testable design hypotheses.
• Produce high-quality outputs in Figma: flows, prototypes, UI specs, and design system contributions.

Research and Evidence-Based Decisions

• Partner with other Product Designers and Product Owners to plan and run usability tests, concept tests, and iterative validation.
• Use behavioral analytics (e.g., event-based insights) to identify friction, measure adoption, and evaluate design impact.
• Utilize research tools like PostHog and Maze to synthesize qualitative + quantitative signals into crisp findings and actionable recommendations.

Systems Thinking and Design Ops

• Contribute to and extend our design system and patterns to support consistency, accessibility, and white-label scalability.
• Collaborate with development teams to ensure designs are feasible, instrumented, and implemented with quality.
• Improve how we work, including templates, critique practices, documentation, and ways of collaborating across teams.

Stakeholder Collaboration

• Work closely with Product Owners, Developers, QA, and client-facing teams to align on scope, outcomes, and trade-offs.
• Present work clearly, showing rationale, evidence, options, and recommended paths.
• Navigate enterprise constraints (compliance, partner requirements, data considerations, and product configurations) while advocating for user value.

Qualifications required:

• Strong interaction design and UX problem-solving abilities – especially across complex, multi-step workflows.
• Has a portfolio that displays solid visual design craft with a high standard for hierarchy, readability, and polish.
• Ability to work end-to-end: discovery → design → delivery → iteration.
• Comfortable using research and analytics to guide decisions and assess outcomes.
• Clear communicator who can explain trade-offs and bring stakeholders along.
• Strong documentation habits (decision logs, specs, rationale, Jira/Confluence fluency).
• Bias toward collaborating with peers, iteration, testing, and learning over “big reveals.”
• Comfortable partnering deeply with Product and Development teams.
• Pragmatic about constraints, but not passive – pushes for better outcomes with smart framing.

The following are nice to have:

• Fintech, wealth-tech, or regulated-industry experience.
• Familiarity with event-based analytics and experimentation practices.
• Experience designing for enterprise platforms, role-based access, or multi-tenant/white-label products.
• Accessibility knowledge (WCAG-informed design decisions).
• Experience contributing meaningfully to a design system (patterns, components, governance).

What to expect:

• An inclusive culture comprised of extremely talented individuals.
• A leadership team with a proven track record of success.
• The opportunity to join a company as it expands across the globe.
• Competitive compensation and generous benefits.

How to Apply:

We’re excited to learn about you and want to give you the opportunity to set yourself apart from everyone else. Along with your Resume, send us a personalized Cover Letter, Email or Video telling us why you are interested in this job, the fintech industry, and the reason you would like to work with us.

Next steps:

If this exciting opportunity is of interest to you, please forward your application as described above with Product Designer – 1 Year Term in the subject line to Human Resources at human.resources@conquestplanning.com by February 18, 2026.

We thank all applicants for their interest. Only those invited for an interview will be contacted.

Conquest Planning Inc. is an equal opportunity employer. Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please contact human.resources@conquestplanning.com.