The Person Behind The Strategy
Hi, I’m Wyndsor. I am a design consultant and strategist with over 20 years of experience leading brand systems and print and digital products.
My focus is the work that happens before production begins. I analyze user flows, commercial goals, and operational limits to build the structural foundation for your visual identity. I provide fractional creative leadership that ties design directly to business revenue, not just aesthetics.
Professional Summary
I specialize in bridging the gap between business objectives and design execution. My career includes designing the foundational e-commerce systems that scaled a startup to a $100M acquisition by Live Nation and directing brand overhauls that yielded 43% increases in sales. Whether building a digital product or launching a print campaign, I ensure the visual output serves a clear commercial purpose.
Core Expertise
Creative Direction & Strategy: Brand Architecture, Product Positioning, Stakeholder Alignment, Client Relations
Digital & UX/UI Design: User Experience (UX) Wireframing, High-Fidelity UI Design, Design Systems, Typography & Color Theory
Print & Packaging: Concept-to-Completion Packaging, Print Production Oversight, Vinyl & CD Layouts, Retail Merchandise Systems
Technical Compliance & Systems: Web Accessibility (WCAG Audits), High-Conversion E-Commerce, Digital Asset Management
Tools: Figma, Adobe Creative Suite, WordPress, Pre-Press Production, Remote Workflows
Professional Experience
Graphic Design Consultant
Wyndsor—Design (Founder)
2006–Present
Wilmington, NC (Remote)
Partner with business owners, marketing leaders, and agencies to solve deep branding and positioning problems that surface-level design cannot fix.
Turn 20+ years of multi-disciplinary business strategy into clear visual assets, digital products, and brand rollouts.
Led the Starr Hill Brewery Rebrand, developing the commercial strategy before designing the visual identity and packaging system from concept to completion. The project led to a 26% YoY portfolio turnaround and a 43% increase in sales for their flagship beer.
Created the brand strategy and visual identity for the Charlottesville Ale Trail, building a flexible brand system that helped grow a grassroots website into an official 501(c)(6) non-profit backed by regional economic development and tourism bureaus.
Embed directly into client remote teams, providing senior strategic guidance while staying hands-on to keep projects moving forward.
Design Director / Senior Designer
Storyware (Contract)
Aug 2021–Present & Early Startup Phase
Charlottesville, VA (Remote)
Note: Re-engaged in 2021 to provide high-level digital product direction after serving as a key creative contractor during the agency's initial startup phase.
UX Wireframing & Architecture: Review client content documents and sitemaps to map out user flows, turning them into structured wireframes that improve user experience and make content easy to read.
Figma-to-WordPress UI: Apply digital branding, typography, and visual design systems to approved wireframes within Figma, organizing clean components for developers to build into responsive WordPress themes.
Web Accessibility: Audit and update digital brand identities for web screens, ensuring color contrast, font legibility, and layouts fully comply with modern WCAG standards.
Collaborative Refinement: Present layouts directly to client stakeholders, leading active feedback sessions to align user experiences with core business goals.
Art Director / Lead Designer
Dave Matthews Band (Full-Time, Contract)
2006–2016
Charlottesville, VA (Remote)
Brand Strategy & Management: Directed the daily visual identity, digital presence, and commercial styling for a globally recognized touring brand over a 10-year tenure.
Album Packaging: Designed the visual concepts and print layouts for the ongoing Live Trax series (35+ CDs/5 vinyl box sets) and updated the iconic Fire Dancer for the Stand Up album cover, which debuted at #1 on the Billboard 200.
Digital Marketing: Designed high-volume email marketing campaigns, website layouts, and targeted web banners to maximize fan engagement and ticket sales.
Merchandise & Product Design: Designed commercial fan merchandise, apparel graphics, and the official annual 12-month wall calendar, consistently reaching a 100% annual sell-out rate.
Creative Director (Startup Acceleration)
Musictoday
1998–2006
Crozet, VA (On-site)
Brand Evolution & Launch: Joined as a Graphic Designer during the early startup phase and earned promotions to Art Director and Creative Director to define the corporate brand and build its digital presence.
Enterprise E-Commerce Systems: Designed the visual strategy and UI layouts for a custom e-commerce portfolio, growing the platform to support 500+ major entertainment clients and driving over $100M in gross annual sales by 2005.
High-Profile Client Management: Managed the digital branding, fan club UI, and custom e-commerce setups for elite global artists, including Dave Matthews Band, the Rolling Stones, John Mayer, Kenny Chesney, the Bonnaroo Music and Arts Festival, Christina Aguilera, AC/DC, and the Grateful Dead.
Team Building & Leadership: Recruited, managed, and mentored an in-house creative team, connecting business goals with daily production to deliver digital products on time and under budget.
Operational Infrastructure: Built and managed internal production lines for high-volume product photography and digital asset management, scaling web image pipelines to support thousands of active commercial items.
Strategic Acquisition Success: Maintained a dual role as senior advisor and hands-on designer, directly contributing to the company's value ahead of its majority-stake acquisition by Live Nation.
Education
The University of Texas at Austin
Bachelor of Fine Arts (BFA) in Design
Selected Client History