Aaron Shepard
Verified Expert in Design
Designer
San Diego, CA, United States
Toptal member since January 9, 2019
Aaron Shepard is a product designer with 20+ years of experience designing complex digital systems, AI-driven products, and data platforms. His work has delivered measurable results, including $70 million in savings at Anthem.ai and a 600% increase in adoption at Deloitte. Aaron specializes in simplifying complex systems, aligning design with business strategy, and creating products that help organizations make better decisions.
Experience
- UI Design - 15 years
- UX Design - 15 years
- Product Design - 15 years
- Prototyping - 15 years
- User Research - 15 years
- Wireframing - 15 years
- Market Research & Analysis - 10 years
- User Flows - 8 years
Portfolio
Caterpillar | Increasing Efficiency for the World's Largest Manufacturer of Heavy Equipment
Renovate America | Improving Financing for Energy Conservation
Beachbody on Demand | Fitness App
Solar Tech
Fitness on Demand
Work Experience
Lead Product Design & Strategy Consultant
Independent Product Design & Strategy Consultant
- Led product design and strategy engagements, helping organizations identify complex product challenges, align design with business strategy, and deliver measurable user and business outcomes.
- Partnered with founders, product, and engineering teams as an embedded design and systems lead across AI platforms, healthcare systems, and enterprise products.
- Led 0 to 1 product definition, system modeling, and platform design across engagements.
- Established system behavior and interaction foundations early to support scalable product growth.
- Aligned product, engineering, and AI teams around clear system direction and decision frameworks.
- Designed for real-world use at scale, translating complexity into usable, trustworthy systems.
Senior Product Designer
Hearst
- Led design of HearstGPT, an AI-native platform supporting multi-model orchestration and agentic workflows.
- Defined how AI agents initiate, surface, and execute actions within real user workflows.
- Designed interaction patterns for system state, feedback, and outcomes to make AI behavior understandable and trustworthy.
- Translated emerging AI capabilities into usable product experiences and actionable product direction.
- Aligned stakeholders by making abstract AI concepts tangible and actionable.
Lead Product Design & Strategy Consultant
Deloitte
- Led design for an enterprise data platform enabling B2B teams to manage, optimize, and evaluate campaign performance across complex workflows.
- Directed a cross-functional team of 20 across Product, Engineering, and stakeholders to align platform strategy and execution.
- Translated fragmented inputs into clear, actionable decision systems for enterprise marketing teams.
- Increased product adoption by 600% through improved system clarity, usability, and decision confidence.
Lead Product Design & Strategy Designer
Compass
- Defined authorization, authentication, and RBAC models for an enterprise platform supporting complex roles and access scenarios.
- Translated complex access logic into clear permission structures, interaction patterns, and predictable system behavior.
- Partnered with Product and Engineering to align permissions architecture across workflows, roles, and product areas.
- Improved usability for access, ownership, and role-based behaviors.
UX Designer
Anthem
- Led the design of an AI-driven platform embedded in clinician workflows for evaluating treatment options.
- Defined how model outputs are surfaced, explained, and interacted with within real-time decision-making contexts.
- Designed interaction patterns that made AI reasoning, confidence, and trade-offs visible to support trust in high-stakes environments.
- Balanced system intelligence with clinician control, ensuring recommendations were actionable without removing human judgment.
- Delivered $70 million annual cost savings while improving adoption, usability, and patient outcomes.
Product Designer
Caterpillar
- Consolidated fragmented workflows into a unified platform, reducing weekly workload by 75%.
- Replaced spreadsheet-driven processes with structured product experiences that improved visibility, planning, and decision-making.
- Facilitated alignment across cross-functional stakeholders to ensure the platform reflected real-world usage and operational needs.
Senior UX Designer
Walmart Labs
- Led product design for Walmart Labs' enterprise testing ecosystem, supporting 30,000+ engineers across continuous integration, functional testing, and performance testing workflows.
- Partnered with engineering leadership to define customer experience strategy, user journeys, and interaction models across a suite of developer productivity tools.
- Redesigned complex testing and execution workflows, reducing task completion time by 25% while supporting 900+ concurrent tests across distributed systems.
- Unified previously fragmented testing experiences into a single platform, helping deliver an estimated 635,000 hours of annual engineering productivity gains across 74 global teams.
Product Designer
Becton Dickinson
- Led research and product design for a tablet-based healthcare investigation platform focused on medication diversion, clinical safety, and operational efficiency.
- Created the information architecture, user flows, journey maps, wireframes, and prototypes needed to support complex investigative workflows from triage through reporting.
- Translated fragmented medication, patient, nurse, and policy data into clearer review experiences, helping clinical teams quickly identify flagged activity and required action.
- Conducted user task and functionality testing to validate proposed features, improve workflow clarity, and deliver up to 50% time savings for nurse managers.
Associate Design Director, Product Marketing
Renovate America
- Led the fintech platform relaunch for Renovate America, a $1 billion financing company, spanning brand, marketing, product architecture, lending flows, and design system foundations.
- Directed a 12-person cross-functional team and external agency to create clearer financing experiences for homeowners, contractors, and lending partners.
- Translated complex qualification, eligibility, and lending logic into guided decision paths that improved trust, clarity, and customer confidence.
- Designed and tested user flows, wireframes, prototypes, and scalable design patterns across discovery, education, application, and conversion journeys.
- Improved the customer eligibility experience, reduced bounce, and contributed to a 44% increase in qualified leads and stronger application and loan performance.
Art Director, Digital Design
Beachbody
- Defined and executed design strategy and art direction for the launch of the digital streaming platform, Beachbody On Demand, generating a significant portion of Beachbody's $1+ billion annual revenue.
- Directed digital art strategy and visual design for multichannel initiatives, including display advertising, social media, affiliate marketing, Amazon marketplace, and broadcast media campaigns across a portfolio of 30+ brands.
- Managed a team of designers, mentoring them to enhance their skill levels and boost their confidence when working with stakeholders.
Creative Director, Principal
Mineral
- Designed award-winning integrated digital solutions, multi-channel marketing initiatives for Fortune 500 and eCommerce clients at a full-service creative agency.
- Leveraged extensive professional network to expand client list, enabling company to become profitable for the first time in eight years and achieve record revenue.
- Acted as principal, refined brand identity, restructured pricing model, and set long-term business objectives that boosted value and competitiveness.
- Cultivated a sterling reputation among clients for delivering work that exceeded expectations, resulting in high-volume referrals from renowned companies across tech, entertainment, auto, and energy industries.
- Worked with various clients, including Toyota, GE, Disney, Gibson, Fender, and Interactions Magazine.
Creative Lead, Web Analyst
ValueClick
- Increased conversions, development of an eCommerce ecosystem through building, delivering and managing creative initiatives, user experiences, promotions and all aspects of site re-design.
- Obtained critical insights, measured customer lifecycles, focusing on reach, acquisition, conversion, retention, and A/B test analysis.
- Decreased annual marketing spend by 600,000, and managed 11 eCommerce properties with annual sales of $28 million.
Director of Advertising
One America Wireless
- Integrated advertising strategy, insights, and creative development to deliver successful advertising programs aligning with brand and marketing initiatives.
Freelance Art Director
Vita Innovations
- Provided art direction at multi-disciplinary design firm serving clients across auto, tech, hospitality, and marketing industries with clients including Ford Motor Company and Squaw Valley Ski Resorts.
Multimedia Designer
Digital Business Products
- Created interactive CD-ROM marketing and sales tools, advertising campaigns, and branded design solutions for HomeStore.com, Realtor.com, Coldwell Banker, 21st Century, Prudential, and RE/MAX.
Web Designer
Digital Imagination
- Developed user interface designs for small to large-scale projects; clients included: Universal Studios, Proctor & Gamble, Morey Body Boards, and Mayfair Capital Group.
Art Director
DotTV Productions
- Delivered innovative and engaging media concepts for clients including Bissell Cleaning Appliances and Coleman Outdoor Products.
Education
Bachelor of Arts Degree in Applied Design with an Emphasis in Graphic Design, Marketing, and Economics
San Diego State University - San Diego, California, USA
Certifications
Design Strategy: Design Thinking for Business Strategy and Entrepreneurship
University of Sydney
Entrepreneurship Bootcamp
MIT
Web Development and Design
Learning Tree University
Skills
Tools
Adobe CC, Zeplin, InVision, InVision Studio, Sketch, Excel 2016, Microsoft PowerPoint, Adobe Photoshop, Adobe Illustrator, Affinity Diagrams, Litmus, Jira, Confluence, Trello, Google Analytics, Miro, Adobe Creative Suite, Microsoft Excel, Adobe Analytics, Flash, Lookback, Zoom, GitHub
Platforms
iOS, Figma, Mobile, Web, MacOS, Apple, Omniture, Dovetail, Vercel, Microsoft
Industry Expertise
Information Technology, Marketing, Pharmaceuticals, Fitness, Sports
Languages
HTML, CSS
Other
Design Leadership, User Testing, Qualitative Research, UX Design, UI Design, Product Design, User Experience (UX), User Interface (UI), Enterprise SaaS, Empathy, User Research, Wireframing, Prototyping, Design Systems, Visual Design, User Flows, Digital Strategy, SaaS, User-centered Design (UCD), B2B, Design Strategy, Pixel Perfect, Responsive Web Apps, Interactive Prototypes, Complex Application User Interfaces (UI), Software as a Service (SaaS), SaaS Design, Journey Mapping, Marketing Tools, UX Research, Usability, Quantitative Research, User Empathy, B2C, Mobile Apps, Mobile App Design, eCommerce, Stakeholder Engagement, Communication, Stakeholder Management, Web App Design, Web Applications, iOS App Design, Leadership, Responsive Web Design (RWD), User Journeys, Mobile UX, Customer Journey, Complex Web Systems, User Workflows, Ideation, Service Design, Direct to Consumer (D2C), Strategy, Research Synthesis, Web App UX, Web App UI, Data Visualization, Dashboards, User Interviews, Interaction Design (IxD), User Stories, Storytelling, Analytics, A/B Testing, Multivariate Testing, UX Pattern Design, Brand Positioning, Information Architecture (IA), User Psychology, Market Research & Analysis, Human-centered Design (HCD), User Profiles, Jobs, Branding, PowerPoint Design, Email Marketing, Performance Marketing, Dashboard Design, Mobile UI Design, Mobile UX Design, DataViz, Workshops, UI Guidelines, Google Drive, Ethnio, Fintech, Residential Real Estate, Testimonial Videos, Jobs to be Done (JTBD), Style Guides, Task Analysis, Personas, Mobile Design, Display Advertising, Brand Guidelines, Photography, Videos, Nutrition & Supplements, User Needs, Solar, Environment, Interviews, Forms, Art Direction, Management, Landing Page Design, Landing Page Optimization, Team Leadership, Entrepreneurship, UX Strategy, Complex Problem Solving, Web Design, Web UI Design, Total Addressable Market (TAM), Research, Startups, Problem Statements, Market Segmentation, Demographic Data, Psychographics, User Personas, Customer Experience, Value Proposition, Customer Acquisition, Financial Projection, Artificial Intelligence (AI), Web UX, Planning, Analysis, Product Strategy, Concept Modeling, High-fidelity Prototypes, Low-fidelity Prototypes, User Validation, Web App Testing, Data Synthesis, Cursor AI, Notion, Supabase, AI-powered Product Design, AI Product Strategy, Systems Design, Data Platforms, AI Systems, Decision Support Systems (DSS), Complex Workflows, CX Strategy, Generative Design, Visual Identity, Collaboration, Creativity, Economics, Business Administration, Finance, Strategic Planning, Business Communication, Competitive Analysis, Value Creation, Value Innovation, Visual Communication, Problem Solving, Design Thinking, Enterprise UX, Human-centered AI, Human-machine Interface (HMI), Bots, Models, ChatGPT, Chatbots, Transparency, Stateflow, Reporting, Marketing KPIs, Growth Metrics, Framing Tradoffs, Cross-functional Team Leadership, Systems Thinking, Stakeholder Alignment
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