VP of Design & Experimentation

Caseware is one of Canada’s original Fintech companies, having led the global audit and accounting software industry for over 30 years, with more than 500,000 users across 130 countries and available in 16 different languages. While you might not have heard of us (yet), over 36,000 accounting and audit professionals list Caseware as a skill on their LinkedIn profiles!

The audit & assurance profession is the foundation of trust in our financial system and global economy—an essential mission undergoing profound transformation. In a rapidly evolving technology landscape, accountants require world-class tools to enhance trust, drive efficiency, and elevate their impact.

At Caseware, we are at the forefront of this transformation, defining and building the future of Accounting technology.

We are seeking a VP of Design & Experimentation to join our Product & UX Team at Caseware, a leading SaaS organization. As VP, UX, you will play a critical role in shaping the future of design, experimentation, and AI-powered innovation, ensuring that our products are both cutting-edge and user-centric.

You will work closely with Product, Engineering, AI, Data Science, and GTM teams to define a UX strategy that is AI-first, data-driven, and customer-obsessed—transforming complex workflows into seamless, intuitive experiences.

📍 Location:

This is a hybrid role requiring the successful candidate to work three (3) days a week in our downtown Toronto office, located at 351 King St E, Toronto, ON. GTA preferred, but open to remote candidates within Canada for exceptional hires.

Contact:

Chengeer Lee - Principal Talent Acquisition Partner & Coach

What will you be doing:

• Lead AI-Centered Design & Experimentation – Define the vision for next-generation UX, integrating AI-driven prototyping, rapid iteration, and user-centered experimentation into product development.
• Build Scalable, Customer-Driven Design Systems – Establish and evolve a highly adaptable, componentized design system that supports rapid innovation and ensures consistency across products.
• Prototype & Test at Speed – Lead high-velocity design sprints and hypothesis-driven experimentation, ensuring product iterations are grounded in real customer insights.
• Optimize Workflow Intelligence – Solve complex, regulated, and high-trust workflows in audit, compliance, and fintech, ensuring solutions are both innovative and deeply relevant to professionals.
• Cross-Functional Leadership – Work closely with Product, Engineering, AI, and Data Science teams to ensure a seamless, end-to-end product experience that aligns with the broader company vision.
• Scale & Mentor a World-Class UX Team – Recruit, develop, and lead a high-performing design team, fostering a culture of creativity, experimentation, and executional excellence.
• Shape the Future of AI-Driven UX – Champion AI-powered tools and workflows, ensuring that AI is embedded into the design process to create intelligent, adaptive user experiences.
• Drive Data-Informed Decision-Making – Implement and advocate for a hypothesis-driven, experimentation-led approach to UX, ensuring continuous learning and innovation.

What you will bring:

• Proven Design Leadership: 10+ years in UX, including leadership roles at the Director/VP level in a SaaS or B2B environment.
• AI & Automation Expertise: Strong understanding of how AI is transforming design, prototyping, and workflow automation.
• Design Systems Mastery: Experience leading scalable, enterprise-wide design systems that drive consistency and efficiency.
• Prototyping & Hands-On Execution: Ability to prototype, iterate rapidly, and work closely with developers to bridge design and engineering.
• B2B SaaS Experience: Background in high-trust, workflow-heavy products such as fintech, audit, compliance, or enterprise platforms.
• Customer-First Mentality: Passion for solving real customer problems and ensuring that UX enhances efficiency and usability.
• Cross-Functional Leadership: Strong collaboration skills with Product, Engineering, AI, and Data Science teams to drive innovation.
• Thought Leadership in UX & AI: A track record of pushing boundaries in design, AI experimentation, and user research.
• Toronto-Based (Preferred): Strong preference for GTA-based candidates; however, open to remote candidates in Canada for exceptional talent.

What's in it for you?

• Lead the Future of AI-Driven Design – Define and execute a bold vision for AI-powered UX, workflow automation, and rapid experimentation in fintech.
• Own a Greenfield Opportunity – Build and scale next-gen design systems and AI-driven prototyping with no legacy constraints, shaping the future of our products.
• Be a Strategic Executive – Report directly to the CPO, influence cross-functional teams (Product, Engineering, AI, Data Science), and operate as a peer to VP-level leaders.
• Drive High-Impact, Customer-Centric Innovation – Solve complex, high-trust workflows in audit, compliance, and fintech, transforming professional-grade software into intuitive experiences.
• Scale & Mentor a World-Class UX Team – Build a best-in-class team focused on experimentation, AI-first design, and high-impact product development.
• Join a High-Growth SaaS Leader – Be part of a fast-scaling, investor-backed fintech company redefining how accounting, audit, and compliance professionals work.
• Hybrid Work, Toronto HQ – Work onsite 3 days a week at our downtown Toronto office, fostering collaboration with top-tier design and product talent. Remote flexibility available for exceptional candidates across Canada.

About Caseware

Caseware’s cutting-edge software products are meticulously designed for accounting firms, corporations, and governments. Our teams continuously collaborate, innovate, and build upon our existing suite of products. With a customer-focused mindset, we are shaping the future of audits, financial reporting, and financial data analytics.

With a strategic investment from Hg Capital in 2020, Caseware is now in its next major growth phase, doubling down on the people and products that have made us successful.

One of our core values is Many Voices, One Team, and we are dedicated to building diverse, equitable, and inclusive teams that reflect our global customers. We welcome candidates of all backgrounds to apply.

If you require accommodations or have any questions during the application process, please contact our People Operations team at [email protected].

Any candidates receiving an offer will need to successfully complete a background check through Certn.co, including an Identity Verification and Criminal Record Check. Executives and Senior Managers may also undergo a Soft Credit Check.