Stefan Regehr Product Design Leader Waterloo, ON
Stefan Regehr
Work Experience
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Director of Product Design
Knak - Remote 2025-Present
I lead the incredibly talented Design team at Knak, where we’re reimagining how marketers build and launch world-class email and landing page experiences. My role combines strategic vision with hands-on design leadership—shaping product direction, advocating for user needs, and helping our teams deliver beautiful, intuitive, and accessible experiences at scale.
Key Accomplishments
- Strategic UX leadership and design vision setting
- Cross-functional collaboration with Product, Engineering & Execs
- Team building, mentorship, and performance management
- Opportunity mapping, UX strategy, and continuous discovery
- Scalable design systems and operational excellence
- Accessible, inclusive, and technically feasible design execution
- Executive communication and design advocacy
- Innovation, experimentation, and industry thought leadership
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Principal Product Designer
Knak - Remote 2022-2025
As Principal Product Designer at Knak, I lead the design of our email and landing page creation platform, driving product excellence and innovation in collaboration with cross-functional teams. My work has significantly improved user experience, contributed to strategic product direction, and elevated the role of design across the organization.
Key Accomplishments
- Led the end-to-end design of major features including AI Assistants, Global Navigation, Dynamic Content, Bulk Sync, Carousels, and Figma integration—ensuring scalable, user-friendly experiences.
- Drove the redesign and implementation of our design system, introducing responsive components, CSS variable theming, and full Light/Dark mode support.
- Built and mentored a high-performing design team, introducing team rituals, feedback frameworks, and growth plans that foster creativity and ownership.
- Established UX research and opportunity mapping processes to align design priorities with customer needs and business outcomes.
- Championed cross-functional collaboration through workshops, backlog triads, and product vision sessions—strengthening alignment between Design, Product, and Engineering.
- Contributed hands-on front-end expertise, designing and developing high-quality prototypes and production-ready UI enhancements in Vue.js.
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Senior UX Manager
Arctic Wolf - Hybrid 2021-2022
As Senior UX Manager at Arctic Wolf, I led the strategic evolution of UX across the organization, building a scalable research practice and design team while embedding user-centered thinking into product development. I was responsible for setting the UX vision and aligning it with the company’s broader goals.
Key Accomplishments
- Founded the UX Research department, hiring the first researcher and establishing a framework of responsibilities, competencies, and team culture focused on continuous discovery.
- Drove a 30% increase in user engagement through strategic product and UX improvements informed by user research and behavioral insights.
- Co-led the development of a scalable React-based design system that reduced design debt by over 20% and improved consistency across the product suite.
- Mentored a multidisciplinary team of 8 designers, researchers, and interns—supporting multiple internal promotions and fostering a high-performing, collaborative team culture.
- Worked cross-functionally with Product and Engineering to integrate UX strategy into roadmap planning, helping shape product direction at a strategic level.
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Design Lead
InFlight Corporation - Hybrid 2015-2021
As Design Lead at InFlight, I led the design vision and execution for the InFlight UX platform—modernizing legacy enterprise workflows through a system of advanced UI components and design patterns. I played a cross-functional leadership role across multiple product verticals and large-scale client implementations.
Key Accomplishments
- Directed the creation and maintenance of a robust design system that powered multiple enterprise products, improving design consistency and reducing UI development effort across teams.
- Led the UX strategy and delivery for key product lines including Aura (Candidate Experience), Employee Experience Portal, and Student Experience Portal—used by Fortune 500 companies, government agencies, and universities.
- Improved user satisfaction by 30% through iterative, data-driven design informed by feedback and usability testing.
- Collaborated with Sales, Marketing, Product, and Engineering to align UX efforts with customer pain points and business priorities.
- Served as a design consultant for large client implementations, guiding user experience decisions and integrating best practices tailored to each enterprise’s needs.
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Senior Product Designer - Team Lead
D2L Corporation - Kitchener Office 2007-2015
As Senior Product Designer and Team Lead at D2L, I led the design of the Brightspace Learning Environment—used by millions of students, educators, and parents globally. I drove end-to-end product design, integrating user insights and agile practices to deliver impactful, scalable experiences in education technology.
Key Accomplishments
- Led the design and implementation of new core features, collaborating with the UX Platform team to resolve usability issues and elevate design consistency across the product suite.
- Championed a transition to agile UX workflows, embedding user feedback into every sprint and development cycle to accelerate iteration and reduce design-to-release time.
- Conducted extensive user research with diverse audiences including teachers, administrators, students, and parents—translating insights into actionable product improvements.
- Created personas, journey maps, and task flows that shaped product priorities and guided design strategy.
- Designed and facilitated workshops, focus groups, and on-site research sessions to align stakeholders and surface high-impact user needs.
- Mentored and hired all new Product Designers, fostering a collaborative and user-centered design culture across the UX team.
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Senior Business Information Specialist
Manulife Group Benefits - Kitchener Office 2005-2007
As Senior Business Information Specialist at Manulife, I designed and developed internal tools to improve operational efficiency and streamline complex business processes for claims management and analytics. Reporting directly to the Director of Business Intelligence, I played a hands-on role in system design, front-end development, and stakeholder collaboration.
Key Accomplishments
- Designed and built web-based applications that automated business workflows—reducing manual input and turnaround times for claim processing.
- Led requirements gathering sessions with internal stakeholders, translating business needs into functional specs and interface mockups.
- Developed interactive dashboards and reporting tools that enabled ongoing data-driven analysis and performance tracking for leadership teams.
- Produced detailed technical documentation and design assets to ensure maintainability and cross-team clarity.
- Collaborated closely with a small internal development team to deliver scalable internal tools that enhanced decision-making and operational visibility.
Competencies
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Design Leadership
Knak, Arctic Wolf, InFlight, D2L, Manulife - 2003 - Current
With over 15 years of experience, I’ve led and scaled high-performing design teams in both enterprise and SaaS environments. At Knak, I built a growing Product Design team from scratch, introducing career development frameworks and strong design rituals. At InFlight, I established the design function and hired a cross-functional team of Product Designers and UI Developers. I believe in leading with empathy, building inclusive teams, and aligning design impact with business goals. My leadership style emphasizes trust, transparency, and continuous learning.
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Product Design
Knak, Arctic Wolf, InFlight, D2L - 2007 - Current
I specialize in crafting intuitive, user-centered digital products that deliver business and user value. I’ve led the design of key features across platforms—ranging from enterprise security tools to low-code marketing platforms. I focus on turning complex problems into elegant solutions, always grounded in research, data, and iterative prototyping. I foster strong design critique cultures and ensure design work aligns with user goals, technical feasibility, and strategic direction.
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Web Development
Knak, Arctic Wolf, InFlight, D2L, Manulife - 2002 - Current
My background in front-end development enhances my ability to design scalable, production-ready UI. I’m fluent in HTML, CSS, JavaScript, and have built apps with frameworks like Vue.js, React, and Angular. My current focus is Vue, which I use to develop design systems, components, and interactive prototypes. I bring a pragmatic approach to front-end development, bridging the gap between design and engineering for seamless execution.
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Lean UX & Agile Development
Knak, Arctic Wolf, InFlight, D2L - 2012 - Current
I work closely with product managers and engineers to define, prioritize, and execute design work in agile environments. I’m experienced in backlog grooming, story mapping, sprint planning, and leading design sprints. I use rapid prototyping and usability testing to validate ideas early, and I regularly facilitate Design Studios and workshops to align teams and accelerate discovery.
Speaking
Monthly R&D Demos
Arctic Wolf 2021-Present
I lead monthly UX demos for all of R&D to share new updates to our Design System, UX Research and product updates that impact the user experience. The demos are short videos that summarize the new features and functionality and usually involve a few bad jokes.
InFlight Annual Offsite - Introducing the InFlight Design System
InFlight 2021
I was the headline speaker at our annual company offsite where I introduced the InFlight Design System to the company. In this presentation I dig deep into the value that the Design System brings and how investing in it will lead to better design, a better product and a more successful business strategy.
From PeopleSoft Developer to UX Designer
Alliance Conference - Las Vegas 2017
In 2017 I travelled to Las Vegas to deliver a presentation on how to use UX Principles as a foundation for UI Development in PeopleSoft.
Making PeopleSoft Accessible
Alliance Conference - Seattle 2016
In 2016 I travelled to Seattle to deliver a presentation on Accessibility best practices and guidelines and how to use the InFlight solution to transform any PeopleSoft application into a modern and mobile optimized fully accessible experience.
Getting PeopleSoft in Shape for Mobile
Collaborate Conference - Las Vegas 2016
In 2016 I travelled to Las Vegas to deliver a presentation on Mobile use cases and how InFlight technology can make mobile so much better.
Design Presentation - Grade 9 class at St. John's-Kilmarnock High School
D2L Office - Waterloo 2014
In 2014 I presented to the Grade 9 class of St. John's-Kilmarnock High School about product design and the design process at D2L.
Planning and Presenting Courses in Learning Environment
Fusion Conference - Denver 2011
In 2011 I travelled to Denver to deliver a presentation on the new Calendar and Task Management tool.
Seating Charts - A New Virtual Classroom for Managing Participation and Attendance
Fusion Conference - Denver 2011
In 2011 I travelled to Denver to deliver a presentation on the new Seating Chart tool. The turnout for the presentation was close to 150 people and a lot of interest in the Product and User Testing.
Architecting Your Course with Desire2Learn Course Builder
Fusion Conference - Chicago 2010
In 2010 I travelled to Chicago to deliver a presentation on the new Course Builder tool. The turnout for the presentation was close to 200 people and I was nervous to say the least. I ended up getting voted as one of the top 3 sessions at the conference and I presented a follow up Webinar later in the year.
Education
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Raw Signal Group Blueprint Management Training
Raw Signal Group - Waterloo 2024
Completed the Blueprint Management Training program from Raw Signal Group, focused on leadership in product design organizations. The program covered core management skills including feedback frameworks, one-on-one structures, delegation, goal setting, and building high-performing, inclusive teams. This experience strengthened my ability to lead design teams with clarity and empathy, and to scale design practices within growing product organizations.
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UX Strategy Program
Jared Spool's Center Centre - Online 2022
When I was the Senior UX Manager at Arctic Wolf, I founded the UX Research department and enrolled the UX team in a 9-month intensive UX Strategy Program led by Jared Spool. The program included multiple weekly sessions directly with Jared and focused on integrating strategic UX thinking into product development. We applied these insights to evolve Arctic Wolf’s product prioritization process and elevate the role of UX in shaping product direction.
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Technical Writing Diploma
Humber College - Online 2005
Earned a diploma emphasizing business writing, copywriting methodologies, and graphic design principles, strengthening the ability to communicate complex technical concepts clearly—a crucial skill in design documentation and cross-functional collaboration.
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BA - Honours Philosophy
University of Waterloo - Waterloo 2003
I completed an Honours Philosophy degree with a Minor in Journalism, where I honed my analytical thinking, logic, and persuasive communication skills—key foundations for problem solving in technical and design roles. The program emphasized critical reasoning, structured argumentation, and clear writing, which continue to influence how I approach complex product challenges and cross-functional collaboration.
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Life-long Learning
Coursera, Code Academy, Raw Signal Group - Online 2004-Present
Engaged in continuous learning through platforms like Coursera, Codecademy, Pluralsight, and LinkedIn Learning. Self-taught technical skills, particularly in HTML, CSS, and JavaScript, and applied them directly to projects. This proactive approach to education demonstrates adaptability and a commitment to staying current with evolving technologies.
Volunteering
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Basketball Coach
Wildhawks Basketball - Kitchener 2022-Present
Coach youth teams fostering skill development, teamwork and sportsmanship.
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Campaign Designer
Colleen James Election Campaign - Region of Waterloo 2022-2023
Designed marketing materials and branding for a successful electon campaign, resulting in Colleen James election as Regional Councillor
References
Available upon request