Full-Time

VP of Design & Experimentation

Posted on 3/6/2025

Caseware

Caseware

501-1,000 employees

Provides software for audit and practice management

No salary listed

Expert

Toronto, ON, Canada

Hybrid role requiring three (3) days a week in the downtown Toronto office; GTA preferred but open to remote candidates within Canada for exceptional hires.

Category
Product & UX/UI Design
UI/UX & Design
Required Skills
UI/UX Design
Data Science
Requirements
  • 10+ years in UX, including leadership roles at the Director/VP level in a SaaS or B2B environment
  • Strong understanding of how AI is transforming design, prototyping, and workflow automation
  • Experience leading scalable, enterprise-wide design systems that drive consistency and efficiency
  • Ability to prototype, iterate rapidly, and work closely with developers to bridge design and engineering
  • Background in high-trust, workflow-heavy products such as fintech, audit, compliance, or enterprise platforms
  • Passion for solving real customer problems and ensuring that UX enhances efficiency and usability
  • Strong collaboration skills with Product, Engineering, AI, and Data Science teams to drive innovation
  • A track record of pushing boundaries in design, AI experimentation, and user research
Responsibilities
  • Define the vision for next-generation UX, integrating AI-driven prototyping, rapid iteration, and user-centered experimentation into product development
  • Establish and evolve a highly adaptable, componentized design system that supports rapid innovation and ensures consistency across products
  • Lead high-velocity design sprints and hypothesis-driven experimentation, ensuring product iterations are grounded in real customer insights
  • Solve complex, regulated, and high-trust workflows in audit, compliance, and fintech, ensuring solutions are both innovative and deeply relevant to professionals
  • 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
  • Recruit, develop, and lead a high-performing design team, fostering a culture of creativity, experimentation, and executional excellence
  • Champion AI-powered tools and workflows, ensuring that AI is embedded into the design process to create intelligent, adaptive user experiences
  • Implement and advocate for a hypothesis-driven, experimentation-led approach to UX, ensuring continuous learning and innovation
Desired Qualifications
  • Strong preference for GTA-based candidates; however, open to remote candidates in Canada for exceptional talent

Caseware provides software solutions focused on audit, assurance, and practice management for the financial and accounting sectors. Its main product, Caseware Cloud, is a cloud-based platform that allows accounting firms, government agencies, and corporate finance departments to securely store files, collaborate effectively, and manage operations efficiently. This platform organizes data, making it easily accessible and simplifying the audit process. Unlike many competitors, Caseware operates on a subscription model, ensuring clients receive continuous updates and support. The company's goal is to help clients deliver deeper insights and operate more efficiently, ultimately driving success for both clients and Caseware.

Company Size

501-1,000

Company Stage

Growth Equity (Venture Capital)

Total Funding

N/A

Headquarters

Toronto, Canada

Founded

1988

Simplify Jobs

Simplify's Take

What believers are saying

  • Growing demand for cloud-based solutions supports Caseware's market expansion.
  • AI integration in audit processes aligns with industry trends and Caseware's offerings.
  • Strategic partnerships, like with Validis, enhance Caseware's data collection capabilities.

What critics are saying

  • Emerging AI-driven audit tools increase competition for Caseware.
  • Rapid technological changes may challenge Caseware's feature integration speed.
  • Multiple acquisitions could lead to integration challenges and operational inefficiencies.

What makes Caseware unique

  • Caseware's cloud platform enhances collaboration and data accessibility for accounting firms.
  • The acquisition of Extractly.ai boosts Caseware's intelligent document processing capabilities.
  • Caseware's AI-powered auditing tool, AiDA, improves efficiency and compliance in audit processes.

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Benefits

Hybrid Work Options

Flexible Work Hours

Company News

Montreal Gazette
Apr 8th, 2025
Barry Melancon, Former CEO of AICPA, Joins Caseware as Chair of Global Advisory Board

Barry Melancon, former CEO of AICPA, joins Caseware as chair of Global Advisory Board.

Canadian Business Journal
Jan 21st, 2025
Caseware Acquires Extractly.ai for Innovation

Caseware announced the acquisition of Extractly.ai, a provider of intelligent document processing solutions for accounting and finance teams. This strategic acquisition includes Extractly.ai’s software solutions, Validate and Extractly+, which automate financial statement reviews and optimize workflows. Caseware aims to enhance integration and user experiences. This marks Caseware’s ninth acquisition since Hg Capital's majority ownership in 2020.

GlobeNewswire
Jan 21st, 2025
Caseware Announces Acquisition of Extractly.ai

Toronto, Jan. 21, 2025 (GLOBE NEWSWIRE) - Caseware, a global leader in cloud-enabled audit, financial reporting and data analytics solutions, today announced the acquisition of Extractly.ai, the provider of intelligent document processing solutions that streamline the audit process for accounting and finance teams.

Financial Post
Jan 13th, 2025
Caseware Appoints David Marquis as Chief Executive Officer

Caseware appoints David Marquis as Chief Executive Officer.

Accounting Today
Jan 7th, 2025
Caseware to acquire lease software company

Audit and accounting data solutions provider Caseware announced the acquisition of Atlanta-based SaaS provider LeaseJava.

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