Barry O'Sullivan

Barry O'Sullivan

Product Design in Toronto, He/Him


Hi, I'm Barry, a product designer and design lead with over 10 years of experience, based in Toronto. With a background in visual identity, I bring a craft-driven approach to creating human-centric digital experiences. Currently open to new opportunities.



Work Experience

2020 — 2022
  • Joined the leadership team at Willful to guide and advise the executive team on product and design strategy and to be the advocate for the end user
  • Established and fostered DesignOps and organizational practices, introducing Notion as a company and department wiki to establish and document workflows and streamline processes
  • Principle designer on major product releases such as our product expansion into Quebec, new features such as a new asset list document, new plan bundles, notifications and testamentary trusts flexibility
  • Established a rolling UX research program to conduct regular semi-structured interviews and usability testing with existing and new users, ensuring constant user feedback, derisking releases and establishing UX benchmarks
2020 — 2020
  • Founding designer of a zero-to-one startup establishing visual identity, information architecture, design patterns and product strategy for Willful’s marketing website and web app
  • Introduced usability testing frameworks for the initial and subsequent product launches and cultivated user-centric product and design strategy
  • Designed project plan frameworks that align business and user goals, gather leading data, establish and track success metrics and employ user feedback
  • Facilitated the launch of a redesign of the Willful platform that helped accelerate sales from 10k/month to over 200k/month within the first year
2018 — 2020
  • Visual Design lead on key projects including the Dicks Sporting Goods design system documentation website, responsive website and Zept's react native app
  • Worked closely with the Director of Design and senior executives to establish DesignOps practices to improve our internal workflows
  • Conducted interviews and usability testing with stakeholders and users
  • Regularly met with and mentored two junior designers
  • Delivered three lunch and learn presentations to the wider Rangle team with 100-150 participants
2015 — 2018
  • Established and improved user experience methodologies, introducing agile concepts and usability testing to outdated waterfall practices
  • Lead the design for key accounts such as Aviva Canada, Deloitte and Sun Life Financial
  • Mentored junior designers and design interns