Senior UX/UI Designer – Enterprise Applications

8–12 Month Contract | Remote-First | Greater Toronto Area

Contract Rate: $60–$75/hour CAD, based on experience and qualifications

Position Status: This posting is for an existing vacancy.

Location: Remote-first within the Greater Toronto Area, with occasional in-person meetings at TSG's Thornhill office and client locations. Preference will be given to candidates located in the northern GTA who can readily attend in-person meetings when required.

Contract Term: Initial 8-month engagement with anticipated extension up to 12 months based on project requirements.

The Siroky Group Inc. (TSG) is a Canadian software development and consulting company specializing in technology solutions for the Out-of-Home advertising industry.

TSG is undertaking a significant modernization of a suite of enterprise applications used to manage complex advertising operations. We are looking for an experienced Senior UX/UI Designer to lead the UX direction for this initiative and help establish a scalable design foundation that can be applied across TSG's broader product suite.

This is not a marketing website or consumer application design role. Our applications support complex workflows involving campaign planning, inventory, mapping, pricing, contracts, production, operations and financial processes. The challenge is to make sophisticated functionality significantly easier and more intuitive for users without sacrificing the capabilities they rely upon.

The Role

Working closely with TSG's Product Owner, Business Analysts, Project Manager, technical teams and client subject-matter experts, the Senior UX/UI Designer will lead the UX discovery and design process for a major enterprise modernization initiative.

A key part of the engagement will be establishing the UX standards, design system and working practices that can be maintained and extended by TSG's internal product team following completion of the engagement.

Key Responsibilities

• Lead UX discovery sessions with business users, subject-matter experts and product stakeholders.
• Understand existing workflows, user behaviours, pain points and opportunities for simplification.
• Translate complex business requirements into intuitive user experiences.
• Establish the overall UX direction and interaction patterns for the modernized applications.
• Lead the design of complex workflows involving campaign planning, inventory selection, mapping, pricing, dashboards, approvals and operational processes.
• Develop user flows, information architecture, wireframes, interactive prototypes and detailed interface designs.
• Establish and maintain a scalable design system, reusable components and UX standards across the project.
• Modernize complex legacy desktop workflows for responsive web-based applications.
• Work closely with Business Analysts and Product Ownership to ensure designs accurately reflect business requirements and user needs.
• Collaborate directly with development teams to ensure designs are technically practical and implemented as intended.
• Lead iterative design reviews with client stakeholders and incorporate feedback throughout development.
• Support usability testing and refinement throughout development and UAT.
• Ensure accessibility, usability and responsive behaviour are considered throughout the design process.
• Produce development-ready designs, specifications and supporting documentation.
• Review implemented functionality for consistency with approved designs.
• Provide UX leadership and mentorship to an intermediate UX/UI Designer.
• Review and provide direction on designs produced by other UX/UI resources.
• Help establish sustainable UX practices and documentation that allow TSG's internal team to continue evolving the products following completion of the engagement.

What We're Looking For

• 7+ years of UX/UI, product design or enterprise application design experience.
• Significant experience designing complex enterprise, B2B or SaaS applications.
• A portfolio demonstrating sophisticated application design, including information-heavy screens and complex workflows.
• Demonstrated ability to simplify complex business processes without removing functionality users genuinely require.
• Experience modernizing legacy desktop or enterprise applications for the web.
• Strong proficiency with Figma or comparable modern UX/UI design tools.
• Experience creating information architecture, user flows, wireframes, interactive prototypes and production-ready interface designs.
• Experience establishing and maintaining design systems and reusable component libraries.
• Strong understanding of responsive web application design.
• Strong understanding of accessibility and modern usability principles.
• Excellent written and verbal communication skills.
• Experience facilitating discovery sessions and working directly with business users and enterprise stakeholders.
• Experience collaborating closely with Product Owners, Business Analysts, developers and QA teams.
• Ability to provide constructive design direction and mentorship to other UX/UI resources.
• Comfortable working iteratively within an Agile software development environment.

Experience with mapping/GIS applications, media planning, advertising technology, CRM, ERP, financial systems, dashboards or other complex operational platforms would be considered an asset.

The Person We're Looking For

You enjoy complicated problems.

When presented with a screen containing 40 fields, six buttons and three decades of accumulated business rules, your instinct isn't simply to make it prettier — you want to understand why the user needs each one and whether there is a better way to accomplish the same task.

You understand that good enterprise UX isn't about removing complexity that the business genuinely requires. It's about organizing that complexity so the application feels understandable, efficient and predictable.

You are comfortable leading conversations with experienced business users, challenging assumptions, testing ideas and collaborating closely with developers until the experience works in the real world.

You are also comfortable building something that will eventually be handed over. Success in this engagement means not only delivering excellent designs, but leaving TSG with a strong design system, clear UX standards and an internal UX resource capable of carrying that work forward.

Contract Engagement

This engagement is intended for an individual contractor who will personally perform the role throughout the engagement. TSG is seeking a dedicated individual resource rather than an agency-based or rotating consulting model.

The engagement is expected to average up to 40 hours per week, based on project requirements.

How to Apply:

Our online application will give you the option to apply to this role as a complete person – not just a resume. The application will assess your qualifications, personality traits and workplace preferences. It should take 10 to 15 minutes to complete. After submitting, you'll receive an email inviting you to log in and view your assessment results.

We will review applications submitted via the online application, with priority given to those who have completed the assessment. We will not consider or accept applications sent directly via email or standard post.

We thank everyone for their interest. We will only contact individuals selected for the next step in our hiring process.

Accessibility & Accommodations
TSG is committed to providing an accessible recruitment process. Accommodations are available upon request for applicants with disabilities throughout the recruitment and selection process. If you require an accommodation during this process press the help button and send us a note.