Transforming TIAA.com
TIAA (Teachers Insurance and Annuity Association of America) is a leading financial services organization dedicated to supporting the financial well-being of individuals in the academic, nonprofit, medical, and public sectors. With over 100 years of history, TIAA is trusted by millions for its retirement, investment, and insurance solutions.
Redefining digital experiences inside a complex enterprise environment
TIAA sought to modernize their website to better serve their audience. Initially, they engaged an external agency to lead the redesign, but as the project progressed, it became clear that the ongoing needs of the website required a dedicated internal team. A Creative Director was brought on board and began assembling a foundational team. This new team was tasked with creating a comprehensive UX strategy, building a design system from scratch, and working collaboratively with developers, stakeholders, and senior executives to ensure the website was scalable, user-friendly, and aligned with TIAA’s long-term digital goals.
Project Overview
Role
Sr. Product Designer
Tools
Figma
Timeline
Jan 2023 – Aug 2024
Jan 2025 – Current
My Primary Focus
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Skills Applied: UX Strategy & Research, Design System Development, Cross-Functional Collaboration, Information Architecture, Stakeholder & Executive Communication, User-Centered Design
Background
When TIAA partnered with an agency to overhaul its web experience, the company lacked an in-house product design team to carry the work forward. A Creative Director was brought on board through a creative recruiting agency and began assembling a foundational team.
My Role
I was hired as a Senior Product Designer to support and ultimately lead key facets of this transformation. Though brought on to lead the B2B UX and redesign initiative, I quickly expanded my impact across multiple tracks of work, including the B2C experience.
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I acted as a multi-disciplinary force within a lean team of specialists — including a systems designer, UX designer, and visual designer. Drawing from my background in branding, UX, and design systems, I was able to fill gaps across the entire design process:
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UX & Information Architecture: Leveraged my experience as a UX designer to help restructure the site’s IA and ensure usability across enterprise flows.
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Systems Design: Supported the creation and evolution of a scalable design system to maintain consistency across both B2B and B2C experiences.
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Visual Design & Branding: Applied my background in visual and brand design to align new UI patterns with TIAA’s evolving identity.
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I collaborated closely with business partners, stakeholders, and cross-functional team members to define priorities, shape strategic direction, and ensure the delivery of intuitive, high-impact solutions.
The Challenge
When I joined the team, there was a need for an internal design infrastructure. We had a few incomplete designs passed over from the previous agency. Timelines were tight, direction was unclear, and the environment needed operational structure for meaningful collaboration and delivery.
My Approach
From day one, I recognized the need to establish foundational systems — not just for design execution, but for team alignment and stakeholder visibility.
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UX Collaboration & IA Development: I facilitated and participated in collaborative UX workshops, engaging business partners early to gather insights and co-create solutions. Partnering with our UX designer, I developed key IA flows and made strategic recommendations to bring structure to a fragmented experience.
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Design File Organization & Process Building: I introduced a rigorous file organization system in Figma — including color-coded frameworks, embedded documentation, and scalable in-file components. This system not only helped streamline the team’s workflow, but also gave business partners and stakeholders a consistent, visual way to track progress across both B2B and B2C efforts.
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Enabling Cross-Team Consistency: My organizational frameworks became a backbone for both teams, increasing transparency, reducing duplication of effort, and setting a new standard for how design work was created, managed, and shared.
Navigating Challenges
As with many enterprise-level redesigns, part of the challenge wasn’t just the work — it was shifting mindsets.
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Design Maturity: When I joined, the design function was still in its infancy at TIAA. Business partners weren’t accustomed to collaborating with product designers and often viewed our team as tactical support rather than strategic partners. Much of my early effort involved educating stakeholders on the value of UX, content strategy, accessibility, and the realities of designing within development and CMS constraints.
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Championing Structure in a Chaotic Environment: Leadership struggled with process and team structure. I had to lead from within, often introducing systems and frameworks to help the team stay organized, track work, and communicate effectively. Over time, these efforts helped stabilize our workflow and earned credibility with partners.
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Design vs. Business Control: Business partners would often take over strategy conversations and made design directives that didn’t align with user needs or platform capabilities. I advocated for the role of the design team respectfully when necessary. It sparked deeper conversations about roles, responsibilities, and the importance of trusting subject matter experts.
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Technology Constraints: Designing within AEM (Adobe Experience Manager) came with unique limitations. I had to balance creative intent with technical feasibility, working closely with developers to understand what was possible within the CMS while still advocating for a high-quality, accessible experience.
Role
Sr. Product Designer
Tools
Figma, JIRA
My Primary Focus
Menu Builder
Timeline
Jun 2022 – Mar 2023
Skills Applied: Stakeholder Engagement, Adaptability & Flexibility, Problem-solving, Empathy, Agile & Lean UX Methodologies, User Research, Proto-personas, User Journeys, Assumption Mapping, Impact vs. Effort Matrix, Flow Diagram, UI Kit, Hi-fi Wireframing, Prototyping
Lack of Design Maturity
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When I joined, the design function was still in its infancy at TIAA. Business partners weren’t accustomed to collaborating with product designers and often viewed our team as tactical support rather than strategic partners. Much of my early effort involved educating stakeholders on the value of UX, content strategy, accessibility, and the realities of designing within development and CMS constraints.
Championing Structure in a Chaotic Environment
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Our Creative Director, though talented creatively, struggled with process and team structure. I had to lead from within, often independently introducing systems and frameworks to help the team stay organized, track work, and communicate effectively. It was an uphill battle at times, but over time, these efforts helped stabilize our workflow and earned credibility with partners.
Design vs. Business Control
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One of the more difficult dynamics was with a business partner who often took over strategy conversations and made design directives that didn’t align with user needs or platform capabilities. I advocated for the role of the design team, pushing back respectfully when necessary. While this occasionally led to friction, it also sparked deeper conversations about roles, responsibilities, and the importance of trusting subject matter experts.
Technology Constraints
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Designing within AEM (Adobe Experience Manager) came with unique limitations. I had to balance creative intent with technical feasibility, working closely with developers to understand what was possible within the CMS while still advocating for a high-quality, accessible experience.
Navigating Organizational and Cultural Challenges
As with many enterprise-level redesigns, part of the challenge wasn’t just the work — it was shifting mindsets.
Lack of Design Maturity
​
When I joined, the design function was still in its infancy at TIAA. Business partners weren’t accustomed to collaborating with product designers and often viewed our team as tactical support rather than strategic partners. Much of my early effort involved educating stakeholders on the value of UX, content strategy, accessibility, and the realities of designing within development and CMS constraints.
Championing Structure in a Chaotic Environment
​
Our Creative Director, though talented creatively, struggled with process and team structure. I had to lead from within, often independently introducing systems and frameworks to help the team stay organized, track work, and communicate effectively. It was an uphill battle at times, but over time, these efforts helped stabilize our workflow and earned credibility with partners.
Design vs. Business Control
​
One of the more difficult dynamics was with a business partner who often took over strategy conversations and made design directives that didn’t align with user needs or platform capabilities. I advocated for the role of the design team, pushing back respectfully when necessary. While this occasionally led to friction, it also sparked deeper conversations about roles, responsibilities, and the importance of trusting subject matter experts.
Technology Constraints
​
Designing within AEM (Adobe Experience Manager) came with unique limitations. I had to balance creative intent with technical feasibility, working closely with developers to understand what was possible within the CMS while still advocating for a high-quality, accessible experience.
Navigating Organizational and Cultural Challenges
Discover
The initial phase of the web app redesign was all about understanding. I aimed to grasp their target audience’s needs, desires, and challenges. I was able to gain an understanding of the users, laying the foundation for the design process.
Insight into the problem
User Research
Before Jenny Craig hired our team, they conducted their own survey on their U.S. Menu Builder to gather customer preferences for a more user-friendly interface. After I analyzed the feedback,
I identified four primary user pain points.
These insights were crucial in identifying three main issues with their menu customization:
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An outdated appearance, which was particularly noticeable on mobile interfaces.
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Poor navigation, a significant hurdle for users accessing the menu builder on smaller screens.
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A lack of information, an aspect that needed enhancement for a more informed and seamless 
user experience.
Original U.S. menu customization screen
Because of Jenny Craig’s tight timeframe and limited budget, I utilized Baymard, a reputable source for e-commerce user experience research, saving time and effort. By leveraging their research database and annotated page layouts, particularly those related to websites offering meal plan subscriptions, I was able to understand typical usability issues and learn about established solutions. This enabled me to make informed design decisions, minimizing trial and error and leading to more efficient solutions.
Proto-personas
To guide the redesign of Jenny Craig's Menu Builder web app, I crafted three proto-personas: Sarah, David, and Ella. These personas represented key segments of the audience, helping tailor the design to genuine needs and challenges.
User Journeys
Dive into the user journeys of Sarah, David, and Ella, offering insights into their interactions, emotions, and challenges as they navigate Jenny Craig's Menu Builder web app.
Define
The focus was to efficiently transform gathered data into clear insights, synchronize the team's perspective on major challenges, and identify core opportunities. This ensured my design strategies were rooted in actual user desires and in harmony with business goals. Speedy iteration, complemented by continuous feedback, drove this phase forward.
The area to focus on
Hypothesis Statements
These hypothesis statements were formulated based on initial observations. When combined, they supported the overarching belief that a tailored Menu Builder for the Oceania region could significantly enhance user engagement and satisfaction.
Assumption Mapping
This map steered efforts in highlighting key areas of focus for both users and the business. It also helped prioritize assumptions based on their project importance and our certainty level, ensuring strategic and informed design decisions.
Defining the Minimum Viable Product (MVP)
Using the Impact vs. Effort Matrix helped prioritize features for the MVP. By engaging stakeholders in this process and considering diverse perspectives, we were able to prioritize features that aligned with business goals and gain buy-in for decisions.
Develop
With a well-defined problem in hand, creativity took center stage. This phase was marked by ideation and exploration. I sketched out design solutions, each aiming to address the challenges identified earlier, and prototypes came to life.
Potential solutions
Flow Diagram
Outlined below is the initial flow diagram capturing the user's journey through the Menu Building and Meal Customization process. This flow provided a step-by-step visualization of the user's interactions and decision points, ensuring an intuitive and seamless experience.
UI Kit
I created a basic UI kit for the design team that adhered to Jenny Craig's brand guidelines. As the project progressed, we expanded and refined this kit, adding more elements to better suit the evolving design and functionality requirements of the web app.
Hi-fi Wireframes & Prototyping
I collaborated closely with the design team to maintain a cohesive user experience, ensuring consistent design across all web app components and aligning each element with the overall aesthetic for seamless user engagement.
A mobile-first design approach was adopted. This strategy allowed focus on creating an accessible, intuitive, and engaging user experience on smaller screens, while ensuring smooth adaptability to larger formats.
After creating an account, users could save their dietary restrictions and preferences. If they needed to modify their choices later, such as switching to a diabetic or vegetarian menu, they could easily do so in their account settings.
Deliver
The delivery phase was about refinement and realization. Every piece of feedback was invaluable, guiding me to tweak and polish my designs. Collaborating closely with developers, we were in the process of ensuring the vision was translated accurately into the final product.
Solutions that work
A Shift in Strategy
In the final phase of our UX design process, we had crafted a Minimum Viable Product. However, in early 2023, following Jenny Craig's acquisition by Wellful, the parent company of Nutrisystem, our MVP did not reach its intended market deployment. This shift in company strategy underscored the ever-changing business environment and its impact on meticulously planned projects.
Rich Learning Journey
Despite not launching, the project offered valuable insights and innovation.
Complex Challenges
Successfully navigated through intricate design and user experience challenges.
User-Centric Design
Focused on deeply understanding and meeting user needs.
Agility in Design
Highlighted the importance of adaptability and flexibility in UX processes.
Reflections on the Unlaunched MVP
Embarking on the design journey for Jenny Craig's web app was a path filled with unique challenges and opportunities.
The process itself was a treasure trove of learning and innovation.
Key reflections from this experience:
Positive Stakeholder Feedback
Gained approval from Jenny Craig's executives for the intuitive design.
Enhanced User Experience
Improved navigation and meal selection, optimizing the overall user interface.
Budget & Time Efficiency
Achieved significant improvements within 
tight constraints.
Even though the MVP did not see its market debut, the insights and designs developed during this project remain a testament 
to the team's ability to create impactful and user-centric digital solutions. The experience was invaluable, equipping me with knowledge and skills that will undoubtedly inform future projects.
As I look to the future, I remain committed to applying my expertise to new challenges, always with an eye towards innovation and user satisfaction.