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Craig E.
Halifax, NS, Canada
Builder of Products, Brands & Teams | From Chaos to Scale | Startup Product & Design Leader
I'm a product and design executive with a 22-year career dedicated to building brands and delivering impactful digital experiences. My journey from design and branding to product leadership gives me a unique perspective, allowing me to see every product as a complete brand and user experience. I specialize in leading product organizations by balancing strategic vision with a hands-on approach. I excel at translating business goals into user-centred solutions and navigating constraints to deliver…
Work
Rafflebox: Evolving into a Scalable SaaS Product
The Challenge: As Rafflebox transitioned from a service-based model to a SaaS platform, its fragmented dashboard and non-linear user flow hindered usability, compliance, and scalability. Users struggled to navigate, complete raffles, and self-serve effectively.
The Impact: I redesigned the product structure and dashboard into a guided, intuitive system that supported all SaaS tiers. The new experience improved accessibility, reduced support dependency, and enabled users to confidently manage raffles end to end.
Provincial Court Scheduling: Streamlining Justice Through Design
The Challenge: The Nova Scotia Provincial Court relied on disconnected spreadsheets and paper calendars, causing delays that conflicted with the Jordan principle of timely access to justice. Each court operated in isolation, creating inefficiencies and scheduling conflicts.
The Impact: I led discovery and design to create a unified, digital scheduling system that gave judges, assistants, and administrators real-time visibility and control. The solution reduced errors, improved coordination, and established a province-wide standard for efficient court scheduling.
Office of Teacher Certification: Digitizing a Paper-Based System
The Challenge: The Nova Scotia Department of Education’s teacher certification process relied on outdated systems and paper workflows, causing delays, data errors, and frustration for both teachers and administrators.
The Impact: I led the product design and service modernization, creating a digital platform that let teachers apply, track, and manage certifications online while streamlining internal review and approvals. The new system reduced admin workload, increased transparency, and improved satisfaction across all user groups.
Rafflebox Play: Transforming the Ticket Buyer Experience
The Challenge: Ticket buyers lacked visibility and control over their raffle experience, leading to confusion, support overload, and lost trust. The initial Player Portal proved the value of self-service but was limited in scope.
The Impact: I led the evolution into Rafflebox Play — a full e-commerce platform where users could purchase, track, and manage raffles seamlessly. The new experience simplified complexity, strengthened transparency, and embodied Rafflebox’s community-focused brand.
Digital Evidence Management: Building a public sector digital system
The Challenge: The Public Prosecution Service relied on a debilitating paper-based system, which was inefficient and insecure for managing, sorting, and sharing legal evidence and documents between various government agencies.
The Impact: I led the full product design and UX research to develop a new digital system from the ground up. This project successfully created a more efficient and secure way for police, prosecutors, and defense teams to access, store, and transmit critical documents.
Rafflebox: Scaling a B2B SaaS platform
The Challenge: The Rafflebox platform’s organic growth had outpaced its original architecture, leading to a confusing user experience and a lack of control over features. The system was non-linear, bloated, and required a full reorganization.
The Impact: I led the product strategy and design to restructure the platform, identifying and monetizing services that immediately increased revenue. By creating a new product taxonomy and a simplified user experience, I established a clear, intuitive system and authored the product guides that now serve as a single source of truth across the company.
Experience
The Wink Collective
Founder/Principal
Sep 2025 - Present
Wink exists to reframe design as a driver of SaaS and business growth, strategic impact, and to close the gap between design education and the realities of the workplace. We work at the intersection of creativity and business: • For Organizations and Startups: Through Wink Consulting, we embed design and product strategy, leadership, user-centred design, and operations to transform design from a cost centre into a growth driver. • For Designers & Teams: We provide mentorship, training, and practical frameworks that build confidence, clarity, and collaboration skills beyond software and craft. With decades of experience spanning product, brand, and user-centred design, Wink helps people and organizations connect creativity with measurable results.
Rafflebox Technologies
Director of Products
Feb 2024 - Sep 2025
Rafflebox Technologies assists charities and non-profits in fundraising through online and in-person raffles, coupling technology with hands-on support to enhance fundraising efforts.
- Built Rafflebox's first Product Department, formalizing the vision into a 10-year roadmap.
- Implemented defined product documentation and AI workflows, boosting cross-functional efficiency by 40%.
- Launched a new user portal, reducing customer support calls by a predicted 50% and achieving 100% customer satisfaction.
- The portal created a new unique market offering and established a connection with a previously ignored user group.
- Identified and monetized free value services, increasing weekly recurring revenue by 12% and strengthening long-term financial health.
What We Make It
Product and Service Design Director
May 2017 - Feb 2024
What We Make It™ is a user experience (UX) design agency specializing in government and public sector agency services. We collaborate with government and public sector team members, stakeholders, and citizens to reimagine the digital delivery of public services.
- Co-founded a sister agency to Kula Partners, building the brand, business model, and core service design processes from the ground up.
- Led consulting on 10+ government digital transformation projects, streamlining critical public services and reducing manual labor and security risk.
- Modernized a legacy teacher certification product into an efficient, self-serve platform, reducing service times and resources by a predicted 40-50%.
- Grew and led a service design team, consulting executive government leadership on product strategy and growth.
- Championed a strategy shift, transforming a legal document product into a comprehensive digital evidence management system that served the full user stream and enhanced security.
Kula Partners
Creative Director
Dec 2015 - Feb 2024
Kula Partners helps B2B manufacturers navigate digital landscapes through tailored marketing strategies, including web design, content creation, and lead generation.
- Successfully conducted countless design pitches, securing approval on design and creative solutions with a 95% first-time success rate.
- As a senior leader, maximized the value of design and contributed directly to company growth and market standing.
- Served as Scrum Master, optimizing project workflows for cross-functional teams (design, dev, marketing) and increasing sprint ship rates from 65% to a consistent 95%.
- This optimization led to faster go-to-market solutions for clients.
- Led creative direction and produced conversion-optimized e-commerce and inbound experiences for a portfolio of global clients.
- Boosted client conversion and business profitability by an average of 25%.
m5
Art Director
Apr 2014 - Dec 2015
A marketing firm that believes real creativity is about going beyond the surface to help solve our clients' big, tangly problems. As one of Canada’s largest independent agencies, they offer all the services you’d expect, plus a few more you might not. All served up in an unpretentious style befitting their East Coast roots.
Think Marketing
Art Director
Mar 2012 - Apr 2014
Generated unique and specific role-related highlights for this experience.
University of Prince Edward Island
Senior Graphic and Web Designer
Jun 2010 - Apr 2012
The University of Prince Edward Island (UPEI) is a public university, offering a diverse range of programs and focusing on research, innovation, and community engagement.
- Played a key role in the university's rebranding initiative, creating a new visual identity that resulted in a 20% increase in international student applications.
- Designed and launched a responsive website that improved user experience, contributing to a 25% increase in online course registrations.
- Collaborated with the academic departments to develop digital marketing materials that highlighted the unique value of UPEI's programs, significantly enhancing student engagement.
- Initiated and managed a social media campaign that raised the awareness of UPEI's sustainability projects, attracting external funding and partnerships.
Graphic Communications Group
Senior Designer
Mar 2008 - Jun 2010
Graphic Communications Group offers a suite of design and advertising services in PEI, specializing in web design, branding, and social media engagement.
- Revitalized a major client's brand identity, leading to a 40% improvement in customer engagement and a significant increase in social media followers.
- Designed a comprehensive online advertising campaign for a tourism agency, resulting in a 30% increase in website bookings during the peak season.
- Implemented a streamlined process for content production, reducing project turnaround times by 25% and increasing the team's project capacity.
- Introduced innovative web design solutions for small businesses, enhancing their online presence and driving an average sales increase of 20%.
Sekonda Limited
Art Director
Jun 2005 - Oct 2007
Since 1966, Sekonda, the top British-designed watch brand for men's watches and ladies watches has taken a 'no time for nonsense' approach to providing customers with great quality watches at a great price.
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