Resume

For over 25 years, I’ve been helping teams turn complex ideas into clear, usable products. I’ve led design strategy in healthcare, FinTech, AI/ML, and life sciences, working with both startups and global enterprises. Whether shaping roadmaps, building teams, or contributing hands-on, I bring a mix of strategy and craft that keeps products moving forward and people aligned.

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Skills

Product Design Leadership, UX Strategy, Product Strategy, UX/UI Design, UX Research, Scalable Design Systems, Design Governance & UX Metrics, Design Operations, Human-Centered Design, Accessibility (WCAG), Agile Product Development, Data-Informed Design, Information Architecture, Cross-Functional Leadership, Stakeholder Alignment, Executive Communication

Domains

Healthcare, FinTech, AI/ML, Revenue Cycle Management (RCM), Clinician Dashboards, BPO Platforms

Software

Figma, FigJam, Miro, Google Suite, Keynote, Jira, Confluence, Linear, Trello, Airtable, Slack


Experience

VP, Product & Design
Toothy AI  | Remote

June 2025 – Present

Leading product and design for an AI-powered revenue cycle management (RCM) platform supporting dental clinics with insurance verification and billing.

  • Designed the BPO platform for verifiers and billing specialists, streamlining insurance workflows.
  • Created a clinician-facing dashboard surfacing billing, claims, and eligibility insights.
  • Defined product vision and design strategy across internal and external RCM tools.
  • Built design processes and governance to ensure compliance, clarity, and scale.
  • Partnered with founders, engineering, and GTM leaders to align roadmap with business goals.
  • Served on the senior leadership team, contributing to company strategy and growth planning.

Senior Manager, Product Design
Qualio  | Remote

October 2023 – April 2025

Led the product design team at a compliance platform helping life sciences companies bring products to market faster.

  • Partnered closely with product and engineering on roadmap planning, aligning on goals and priorities.
  • Balanced strategic leadership with hands-on UX/UI design for high-impact, regulated workflows.
  • Led user research, usability testing, and heuristic evaluations to validate product direction.
  • Interpreted analytics and customer feedback to shape features and identify pain points.
  • Helped maintain and evolve the design system to support speed, consistency, and scale.
  • Mentored designers and supported career growth within the product and design organization.
  • Used tools like Slack, Loom, and Zoom to facilitate async collaboration, design walkthroughs, and team alignment in a fully remote environment.

Vice President, Product Strategy and Design
Via Customers  | Remote

September 2022 – June 2023

Joined the senior leadership team to lead design and product strategy at a B2B2C SaaS company supporting e-commerce brands

  • Collaborated daily with product, engineering, GTM, and customer success teams.
  • Led roadmap planning, aligning product design initiatives with organizational KPIs.
  • Designed and launched a flexible, scalable design system used across multiple teams.
  • Mentored designers and created a growth framework to support team development.
  • Synthesized customer interviews, NPS data, and analytics into design strategy.
  • Contributed to key product features while managing and coaching the broader design team.
  • Co-led a women’s employee resource group to support inclusion and equity.

Senior Director, UX Strategy & Design
Guidea  |  Austin, TX / Remote

May 2014 – Aug 2022

Led UX strategy, research, and product design for primarily enterprise clients, while also supporting startups and SMBs. Focus areas included healthcare, FinTech, and AI/ML-driven fraud prevention.

  • Oversaw client engagements and internal design teams, scaling UX capabilities across multi-year projects.
  • Notable outcomes:
    • 7 product launches across 5 brands for a Fortune 25 healthcare company
    • 5 major releases for a Fortune 200 FinTech client
    • UX work that contributed to 4 client acquisitions valued from multi-million to multi-billion dollars
  • Designed accessible enterprise UX systems compliant with WCAG guidelines.
  • Advised clients on hiring, org design, and DesignOps maturity.
  • Facilitated research-driven workshops to clarify strategy and align stakeholders.
  • Clients included Cigna/Express Scripts, Mastercard, Humana, Bloomberg, Dell, PayPal, Kronos/emLogis, and Honeywell

Freelance UX Strategy, Research & Design
Self employed  |  Austin, TX

Aug 2013 – May 2014

  • Led the UX research and UX/UI design for a non-profit helping parents gain access to educational and therapeutic resources for their young children with special needs
  • Designed branding and marketing materials for startups
  • Provided hands-on creative direction, design, and generative UX research for FinTech and consumer products

Director User Experience & Creative
Moboom  |  Austin, TX

Aug 2012 – Aug 2013

  • Served as part of the operations upper management team for an international startup
  • Led and contributed to all aspects of design, both UX/UI and marketing
  • Designed UX/UI for SaaS product that enabled large companies to quickly generate thousands of co-branded websites for sub-companies and franchises
  • Established brand identity guidelines and designed marketing assets

Associate Creative Director UX
projekt202  |  Austin, TX

Feb 2006 – Jul 2012

  • Managed UX design teams providing creative direction, mentorship, and career guidance
  • Both managed and actively contributed to the UX/UI design of SaaS, B2B, B2C, and B2B2C web applications, native mobile applications, and voice (non-GUI) applications
  • Oversaw the successful design launch of dozens of products across multiple verticals including healthcare, retail, consumer electronics, education & public sector, search & analytics, enterprise & ERP, financial services, e-commerce, entertainment, sports, and media
  • Conducted generative and evaluative UX Research including extensive field research
  • Led strategic and design-thinking workshops with clients
  • Clients included SAP, Motorola, Dell, Microsoft, Kronos, Schwab

Additional Positions
Dallas, TX & Austin, TX

June 1995 – Jan 2005

  • Creative Supervisor at VML
  • Creative Director at DigiTerra
  • Lead Interaction Designer at Parallel Group
  • Marketing Manager at RE/MAX,
  • Inside Sales and Marketing Lead at STB Systems

Additional Interests

  • Award-winning, data-driven abstract artist exhibiting fine art in multiple galleries
  • Data visualization artist with long-term multi-year data collection and visualization projects
  • Photographer, primarily international travel documentation

Website: jeszilla.com