Hi, I'm Jacob Medley.

UX/UI Designer & Digital Strategist


I believe there’s always a better way, and together we can find it. In this portfolio, you’ll see highlights from my design journey so far.

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Case Studies


WebMD

eCommerce Website


Summary:

Internet Brands wanted to open up new opportunities for growth across their portfolio. One of these efforts was combining the strength of WebMD's brand and DentalPlans product.


DentalPlans.com

Product Framework and Design System


Summary:

I led the design and front-end development of product-focused sites for DentalPlans.com. Over the course of a year, what started as a tiny product site initiative evolved into a core component of DentalPlans' business. This initiative developed into a framework for rapidly designing and launching product eCommerce websites for Cigna, Aetna, WebMD, and Lower My Dental Bills (LMDB).


BumblebeeMD

Brand and Product Development


Summary:

I had the privilege to partner with a brilliant brand manager, Tiffany Tibbets, on this project. We worked with executive stakeholders to bring this brand to life. Our goal was to invent a fun and family-focused brand.


Hydra

The Making of a Design System


Summary:

I championed and implemented the Hydra design system, a large-scale project that unified the customer experience across the company's products and streamlined the design and engineering processes.


One Park Financial

Redesign Corporate Website


Summary:

I partnered with the CEO and SVP of Marketing at One Park Financial to redesign its corporate website and lead flow.


Full-Stack Designer


Here are some examples showcasing the diverse skill sets and methods I’ve used to create better user experiences and business outcomes.

Resume


Design Leadership

  • Design Leadership: Directed cross-functional teams to create scalable design systems, ensuring consistency across digital ecosystems and delivering measurable business impact.
  • Strategic Vision: Aligned product and brand design with user needs and business objectives through comprehensive UX roadmaps and prioritized initiatives.
  • Inclusive Design Culture: Fostered a culture of collaboration and innovation by mentoring designers, promoting accessibility standards (WCAG), and encouraging experimentation.
  • Conversion Optimization: Spearheaded conversion rate optimization (CRO) strategies, enhancing user funnels and driving substantial increases in engagement and revenue.
  • SEO and Content Strategy: Developed SEO-optimized website structures, blending technical performance with engaging user experiences to boost search rankings and user retention.
  • AI-Powered Tools: Designed and implemented GPT/LLM-based products, including conversational chatbots and intelligent search tools, to improve customer engagement and operational efficiency.
  • Data-Driven Insights: Applied qualitative and quantitative research to inform design decisions, continuously iterating to exceed user expectations.
  • End-to-End Design Process: Managed all phases of design, from ideation and prototyping to testing and implementation, delivering seamless user experiences across web and mobile platforms.
  • Business-Centric Design: Created user-centered solutions that achieved business goals, such as increasing sales by 47% and reducing project timelines by 66%.
  • Collaboration & Alignment: Partnered with marketing, engineering, and product teams to deliver cohesive brand and product experiences across all touchpoints.

“With the right team, anything is possible. Anything!”


Experience

Director of User and Experience Design
Health-E Commerce, New York, NY (Remote)
Feb 2026 to Present
Director of Design
Feb 2025 to Feb 2026

I joined Health-E Commerce to restructure creative marketing and build an experience design practice the company had never had. Rather than absorbing more requests, I applied systems thinking and UX research methods to identify the right problems to solve, rebuilding intake, process, and creative operations around them. The first year closed with roughly a 70% increase in output against a temporary 6.7% increase in contractor headcount, and one of the smoothest Surge seasons on record — the company’s highest-volume period of the year.

With creative operations stable, we split the department and I moved full time to building the experience design side of the business, a function that had not previously existed. I defined the practice and hired the company’s first dedicated XD/UX designer.


Sr. UX Designer
Mutual of America Financial Group, Boca Raton, FL
2023 to 2025

At Mutual of America, I collaborate with stakeholders and cross-functional teams to identify and resolve key user experience challenges. I lead strategic planning sessions and facilitate workshops to align design objectives and strategies. By defining user-centric epics and crafting detailed user stories and acceptance criteria for the main website, I ensure that our digital products meet and exceed user needs. I established best practices for A/B testing to inform design decisions and optimize usability. Additionally, I contributed to the design and development of a GPT/LLM conversational search application within Salesforce and the public websites.


Director of UX/UI & Product Design
One Park Financial, Coconut Grove, FL
2021 to 2022

At One Park Financial, I oversaw and developed all design processes and workflows, establishing best practices for UX and UI design and usability testing. I collaborated with teams across marketing, product, and engineering, conducting workshops to drive problem-solving and innovation. Partnering with Channel Managers specializing in PPC, SEO, and Affiliate marketing, I helped establish their conversion rate optimization strategies to maximize user engagement and conversion rates.

I evangelized the need for a design system, partnering with the SVP of Marketing to secure executive buy-in for the project. This led to the creation of the Hydra Design System, a unified pattern and component library. This empowered the company to design and engineer rapidly and "fail fast," improving business goals and user experience.


Sr. Manager, UX/UI Design
DentalPlans.com, Plantation, FL
2015 to 2021

I pioneered a design system and code componentization at the company, fostering rapid development and refinement of product features and marketing strategies, crucial for our omnichannel eCommerce platforms. This approach, coupled with DevOps practices and product design for microservices, significantly boosted our testing and iteration capabilities, aligning with product design excellence and business growth.

Leading UX/UI design and development, especially for projects involving product partners, I managed design and development for LAMP stack projects, driving remarkable financial growth. These strategic initiatives resulted in over 47% of new revenue, 27% of total lead generation, and contributed to 20% of the company's overall revenue, highlighting the essential role of strategic product design and development in business expansion and profitability.


Sr. Digital Designer
Bluegreen Vacations, Boca Raton, FL
2011 to 2015

As the design lead, I contributed to the company-wide transition to a data-driven omnichannel marketing platform, incorporating digital signage across 48 resort locations and interactive kiosk interfaces. This role involved crafting engaging user experiences across various marketing platforms and channels, ensuring a seamless integration of digital and physical touchpoints.

In collaboration with stakeholders, cross-functional teams, and external consultants, I played a key role in implementing and integrating a comprehensive marketing experience strategy. This strategy was focused on unifying our messaging and branding across all channels, including the innovative use of digital signage and interactive kiosks, to create a cohesive and dynamic customer journey. My leadership in this area was pivotal in enhancing customer engagement and reinforcing the company's presence in the competitive resort industry.

Expertise

  • Design Thinking
  • Systems Thinking
  • User Experience Design
  • User Interface Design
  • Interaction Design
  • Brand & Visual Design
  • Mobile-First & Responsive Design
  • UX Roadmapping & Prioritization
  • User Testing
  • Facilitating Workshops
  • A/B Testing & Planning
  • Conversion Rate Optimization
  • Wireframing
  • Prototyping
  • Accessibility Standards (WCAG)
  • Designing for B2C & B2B
  • Design Systems
  • Project Management
  • Agile Workflows
  • Writing User Stories & Acceptance Criteria
  • Front-end Development
  • HTML and CSS
  • Less and Sass
  • Bootstrap Framework

Apps & Tools

  • Figma
  • Adobe XD
  • Adobe Creative Suite
  • FigJam
  • Miro
  • Balsamiq
  • Lucidchart
  • Adobe Target
  • Optimizely
  • VWO
  • FullStory
  • SessionCam
  • Hotjar
  • UserTesting.com
  • Userlytics
  • Google Analytics
  • New Relic
  • Splunk
  • Lighthouse
  • ChatGPT
  • VS Code
  • Sublime Text
  • Jira
  • Asana
  • Bitbucket
  • GitHub
  • GitKraken

Education


Degree in Digital Design

Full Sail University, Winter Park, Florida

AI for Designers

Interaction Design Foundation (IxDF)

Design Patterns for AI UX

Interaction Design Foundation (IxDF)

Micro-Usability: How to Design for Frictionless UX

Interaction Design Foundation (IxDF)

Customer Experience: Service Blueprinting

LinkedIn Learning

Hands-On with Design Systems

LinkedIn Learning

Figma for UX Design

LinkedIn Learning

Figma Essential Training

LinkedIn Learning

The Data Scientist’s Toolbox

Johns Hopkins University

Certificate of Membership

Interaction Design Foundation (IxDF)


© 2026 by Jacob Medley

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