I’m a senior product designer who specializes in complex enterprise systems, fintech, and AI-enabled workflows—where the real challenge is getting the rules, permissions, exceptions, and failure behavior right, not just the UI. I translate ambiguous operational requirements into clear, testable behavior: stateful flows, handoffs, escalation paths, and human-in-the-loop patterns that teams can build and verify with confidence. From evaluating live voice agents for claims operations to redesigning core banking experiences under strict legal and accessibility constraints, I focus on outcomes in high-stakes environments. I enjoy aligning design and engineering around measurable behavior and creating systems that help organizations ship faster—like modular interaction patterns and component libraries that reduce friction and improve quality across large, regulated ecosystems.…

Jake Redmond

I’m a senior product designer who specializes in complex enterprise systems, fintech, and AI-enabled workflows—where the real challenge is getting the rules, permissions, exceptions, and failure behavior right, not just the UI. I translate ambiguous operational requirements into clear, testable behavior: stateful flows, handoffs, escalation paths, and human-in-the-loop patterns that teams can build and verify with confidence. From evaluating live voice agents for claims operations to redesigning core banking experiences under strict legal and accessibility constraints, I focus on outcomes in high-stakes environments. I enjoy aligning design and engineering around measurable behavior and creating systems that help organizations ship faster—like modular interaction patterns and component libraries that reduce friction and improve quality across large, regulated ecosystems.…

Available to hire

I’m a senior product designer who specializes in complex enterprise systems, fintech, and AI-enabled workflows—where the real challenge is getting the rules, permissions, exceptions, and failure behavior right, not just the UI. I translate ambiguous operational requirements into clear, testable behavior: stateful flows, handoffs, escalation paths, and human-in-the-loop patterns that teams can build and verify with confidence.

From evaluating live voice agents for claims operations to redesigning core banking experiences under strict legal and accessibility constraints, I focus on outcomes in high-stakes environments. I enjoy aligning design and engineering around measurable behavior and creating systems that help organizations ship faster—like modular interaction patterns and component libraries that reduce friction and improve quality across large, regulated ecosystems.

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Language

English
Fluent

Work Experience

QA Specialist Sr. | AI/Data Foundations Transformation at Sedgwick
June 1, 2026 - Present
Evaluated end-to-end behavior of live-voice agents supporting claims operations, including conversation flows, handoffs, exceptions, escalation, and human review. Translated operational requirements into defined agent behavior, test scenarios, and evaluation criteria. Developed and maintained team-adopted operating processes, evaluation checklists, and project workflows to structure agent development and testing, and organized decisions and dependencies across the voice-agent project.
Senior Product Designer | Independent Practice
September 1, 2025 - Present
Provided senior product design support across compliance-heavy onboarding, enterprise workflows, AI-enabled products, and data-rich internal tools. Translated ambiguous requirements into defined workflows, business rules, permissions, handoffs, exceptions, and failure states. Produced implementation-ready flows, prototypes, and specifications to align product and engineering around complex product behavior.
Lead Product Designer at TD Bank
June 30, 2025 - August 11, 2025
Led UX strategy and delivery for complex financial journeys across web platforms. Mentored cross-functional teams to elevate design craft, accessibility standards, and research-driven decision making. Provided strategic coaching and quality assurance across design teams to elevate craft and ensure timely, high-impact design delivery across journeys and platforms. Collaborated closely with product managers, engineers, and stakeholders to define requirements and prioritize features. Partnered with product, engineering, and compliance teams to design scalable workflows and user flows. Delivered wireframes, high-fidelity mockups, and prototypes using Figma and design systems. Embedded user-centered design practices into enterprise culture via coaching, talent development, and communities of practice.
Senior UX Designer at Purpose Design Co
May 31, 2024 - August 11, 2025
Spearheaded design for embedded AI-chatbot platforms, improving customer engagement. Delivered wireframes, prototypes, and UI systems to streamline onboarding and cross-platform consistency. Mentored junior designers and shaped scalable UX best practices.
UX Designer at OneSpring
December 31, 2023 - August 11, 2025
Designed complex user flows and data-heavy interfaces for enterprise applications. Facilitated design thinking workshops to bridge stakeholder goals and user needs. Built scalable design systems and pattern libraries.
Lead UX Designer at TD Bank
December 1, 2023 - August 1, 2025
Designed and validated core banking flows on a high-availability platform requiring 99.9% uptime across 10M users and 1,050 branch locations. Maintained zero post-launch compliance violations by integrating legal requirements directly into product behavior and interface patterns. Established standardized authentication interaction patterns with deliberate friction for sensitive financial actions and ensured WCAG 2.1 AA compliance through cross-functional alignment among product, engineering, legal, and accessibility teams.
Lead User Experience Designer at TD Bank
December 1, 2023 - August 1, 2025
Online Banking Ecosystem: Lead interaction design for high-traffic financial features; Regulatory & Security Integration: Architect user journeys for compliance while preserving usability; Scaling trust patterns: standardized UI patterns for security and authentication.
UX Designer at Calculai
March 31, 2022 - August 11, 2025
Led UX for MVP launches in AI-powered SaaS platforms. Synthesized user research into elegant, accessible designs with low-friction user journeys.
Senior UX Designer at OneSpring
March 1, 2022 - December 1, 2023
Led transformation of a 15-year-old AS/400 ERP system into a responsive web application, restructuring 100 fragmented screens into 25 scalable interfaces. Reduced executive reporting time from two hours to five minutes by converting 200-field dashboards into clear decision-making interfaces. Enabled three development teams to ship 60% faster by creating a system architecture and component library of 120 reusable patterns, and facilitated design logic workshops aligning 20 stakeholders for enterprise clients handling over $2B in annual transactions.
Senior UX Designer (Contract) at OneSpring
March 1, 2022 - December 1, 2023
Legacy modernization: transform legacy AS400 business software into modern web experiences; Enterprise architecture: apply systems thinking for resilient data flows; Design Systems Management: build scalable UI patterns and libraries.
User Experience Designer (Contract) at Calculai
January 1, 2022 - March 1, 2022
MVP de-risking: synthesize user research into effective UX strategies that support early-stage launches; Engagement optimization: craft intuitive, low-friction onboarding flows.
Business Instructor at Sias University
December 31, 2021 - August 11, 2025
Delivered instruction in CRM, marketing, and strategic management. Created informed learning journeys for online student engagement.
Technical Arts Director at ALIVE Church
August 31, 2020 - August 11, 2025
Led a team delivering worship experiences to a large audience across multiple venues. Created user-centered design strategies, exceeding audience expectations. Conducted weekly reviews to ensure alignment with organizational goals. Managed AV technical systems, delivering high-quality user experiences.
Business Advisor at [Re]THINK Gift Wraps
August 31, 2020 - August 11, 2025
Developed sustainable business strategies through user-focused design thinking. Collaborated with stakeholders to optimize digital operations and environmental impact.
Business Instructor at Sias University
August 1, 2020 - January 1, 2022
Taught business logic and communication principles, refining ability to translate complex concepts for diverse audiences.
Technical Arts Director at ALIVE Church
November 1, 2016 - August 1, 2020
Directed technical production environments, managed cross-functional teams, and ensured operational reliability under tight timelines.
Production Director at Fountain Springs Church
October 31, 2016 - August 11, 2025
Designed and implemented user-centered experiences for worship services. Applied design thinking methodologies, increasing engagement and retention. Managed AV technical systems and budget, ensuring seamless integration with user experience. Designed multimedia content using Adobe Creative Suite, enhancing worship experiences.
Production Director at Fountain Springs Church
January 1, 2015 - October 1, 2016
Oversaw production operations, coordinating teams to deliver events and media across services.
Student Development at Oklahoma Wesleyan University
January 1, 2010 - January 1, 2015
Supported student programs and development initiatives with a focus on communication.

Education

Master of Business Administration at Oklahoma Wesleyan University
August 16, 2010 - May 26, 2012
Bachelor of Science at Oklahoma Wesleyan University
August 13, 2007 - December 12, 2009
Communication Arts
M.B.A. at Oklahoma Wesleyan University
January 1, 2012 - August 11, 2025
B.S. Communication at Oklahoma Wesleyan University
January 1, 2009 - August 11, 2025
Master of Business Administration (MBA) at Oklahoma Wesleyan University
January 11, 2030 - January 1, 2012
Bachelor of Science in Communications at Oklahoma Wesleyan University
January 11, 2030 - January 1, 2009
Master of Business Administration at Oklahoma Wesleyan University
January 11, 2030 - September 23, 2026
Bachelor of Science in Communications at Oklahoma Wesleyan University
January 11, 2030 - September 23, 2026

Qualifications

Add your qualifications or awards here.

Industry Experience

Education, Media & Entertainment, Non-Profit Organization, Transportation & Logistics, Financial Services, Software & Internet, Professional Services
    TD Bank - Online Banking Enrollment Redesign
    TD Bank Online Banking Enrollment Redesign — Jake Redmond Context & Problem TD Bank’s online enrollment was severely underperforming—only 4–9% success rates in self-guided and assisted flows. Friction drove customers to call centers or branches, costing the bank potential adoption by ~700,000 users. My Role & Process As Manager of User Experience Design for responsive web, I led UX and UI redesign—brainstorming, mapping flows, wireframing, prototyping, and testing in partnership with product, legal, architecture, and research teams. Design Sprint & Insights A sprint with cross-functional teams revealed customer frustrations: “It goes sour when trying to enroll for online access.” “Spent hours on hold… still not enrolled.” Users wanted instant access—even before receiving debit cards. Solution Strategy We redesigned the flow into four clear steps: Account Lookup – Tested SSN vs. Last Name + SSN. Findings: most would enter SSN but wanted clarity, confirmation, and transparency on data use. Copy was rewritten to be empathetic and explanatory. Consolidated Terms & Conditions – Moved scattered agreements into one screen, reducing cognitive load. Security Verification – Isolated OTP flow for customization without affecting other areas. Username & Password Setup – Let users choose credentials; avoided auto-filled email usernames due to formatting issues. Design System Integration I pushed for implementing a progress bar from the design system into the responsive codebase, securing a sprint’s resources to deliver it. Outcome & Impact The simplified, step-by-step flow reduced friction, clarified instructions, and improved perceived security. Core improvements: Manageable steps Reduced input burden Unified T&Cs Streamlined OTP verification By aligning stakeholders and applying human-centered design, we positioned TD to exceed industry enrollment benchmarks and convert hundreds of thousands more customers to online banking. UXDesign ProductDesign UserExperience HumanCenteredDesign DesignThinking UXStrategy UIUX CustomerExperience BankingUX DesignSystems UXResearch Prototyping InteractionDesign AccessibilityInDesign DigitalBanking ServiceDesign UXCaseStudy…
    BikeScout
    BikeScout sells bikes on their web experience. I was brought on to improve the conversion from browse to completion of checkout to increase revenue on the product’s web experience. webdesigner designer…
    Wireflow for Stealth mode Startup
    Calculai, a global decision sciences company is working on a new venture - a family-themed app to assist family members as they coordinate their lives around managing their kids well. I was brought on to develop wireframes and user flows for the financial management section of the application. designer uxdesign…