Bryan Connor
Modernizing Tuition Reimbursement in Guild Grow
Project Snapshot
Company: Guild – SaaS platform and marketplace that helps large enterprises offer education benefits to their workforce.
Product Area: Tuition Reimbursement (TR) for Guild Grow. – a core benefit offered alongside Tuition Assistance
Timeline: Q2 2025
As the design lead for this initiative, I was responsible for:
Mapping the existing TR experience for members, employers, and internal Ops teams
Creating prototypes to align stakeholders and gather feedback
Designing a solution mapped to a change management strategy that drives employer adoption, member clarity, and operational feasibility
This project was a high-visibility effort inside Guild: success required coordination across Product Management, Member Ops, and Customer Success, and it directly shaped how some of our largest enterprise customers managed millions of dollars in education benefits.
Problem / Challenge
Tuition Reimbursement (TR) is one of Guild’s most widely used benefits, but the way the offering was structured didn’t effectively serve either members or employers.
Employers were locked into a one-size-fits-all configuration that meant they were often surprised by member (employee) spend. Because eligibility checks were required too close to course start dates, members would enroll and pay out of pocket without their employer having visibility into upcoming costs. That unpredictability made it difficult for employers to manage budgets and led to overspending.
Members had only a short window before starting a course to confirm whether it would be reimbursable. In many cases they were also unaware of eligibility rules and deadlines. These factors resulted in members investing in education that ultimately wasn’t covered.
Our challenge was to redesign the TR benefit and supporting system so that:
Employers could smoothly shift to new rules that enabled better forecasting and spend control or create a custom rule-set.
Members could gain better awareness of rules and had more time to confirm eligibility up front, reducing financial risk.
Support & Ops teams could support the new rules without adding workload or creating manual workarounds.
In short, the product needed to evolve from forcing reactivity to enabling proactivity—all without disrupting ongoing member education and the operation of the benefit at some of our largest accounts.
Approach / Process
We knew that changing the fundamentals of how Tuition Reimbursement (TR) worked would affect three groups at once — members, employers, and our internal ops team. Our approach was designed to uncover and align their needs.
1. Interviews & Journey Mapping the Current State
I started by creating a journey map of the end-to-end TR experience: how members discovered eligibility rules, how employers set policies, and how ops handled exceptions. This helped us pinpoint friction: members often found out about deadlines only when the went to request reimbursement.
In interviews we also uncovered how Member Ops teams had resorted to creating manual workarounds in order to handle exceptions, asking members to submit reimbursement requests with incorrect dates to force the system to accept them.
2. Research & Benchmarking
Internal data showed that 58% of members pay for programs out of pocket before checking whether they were reimbursable. Changing this proportion became one of our overall success metrics.
We also looked closely at competitors’ reimbursement offerings and found that most gave learners more time up-front to confirm eligibility and were more restrictive about post-course reimbursement. These insights reinforced another design goal: shift TR behavior toward proactive eligibility confirmation, while maintaining flexibility for employers with different requirements.
3. Prototyping & Alignment
I created a series of AI-coded prototypes to show how new deadlines, eligibility checks, and exception workflows might look. These prototypes helped us bring Member Ops and Customer Success leadership into the conversation early, building confidence that the new experience would be adopted by employers and could run without adding operational burden.
4. Testing and validation
Making the TR benefit more configurable meant that language in the member experience needed to be dynamic. I ran comprehension testing comparing new language structures against language in the current platform. I found that even the static text in the current state was accurately interpreted by roughly 1 in 2 users. This drove home that new dynamic language had to leave no room for ambiguity.
5. Design Mapped to Change Management
A key challenge was not just redesigning the interface, but designing the transition. Alongside the design work my PM counterpart and I coordinated with Customer Success to craft a comprehensive change management framework that:
Enables new employers to use the functionality on their first day
Included a series of warnings and confirmations in member experience for employers with an existing benefit
Packages suggested comms templates and timelines for employers to use
Introduces the concept of a grace period which could be customized per employer
Defines steady-state enforcement after the grace period ends
Solution
Our research and change management framework directly shaped our solution – reimaging tuition reimbursement as a flexible system encouraging proactive use, rolled out in a phased approach.The solution had three coordinated components:
1. Flexible and Clear Configuration
We introduced a flexible configuration experience that allowed employers to set custom eligibility and reimbursement submission deadlines.
We used data on existing employers to build a series of configuration presets that incrementally increased the tool’s flexibility, and shipped them as defaults for new customers.
The design for the longer term solution didn’t limit employers to presets, allowing them to have total control over reimbursement rules and deadlines. Defaults were set that gave members more time to check eligibility before going out of pocket.
The UX gave administrators a human-readable output that doubled as a preview of the member experience.
2. Dynamic Member Experience
For members, we designed a dynamic, responsive experience that guided them through the new deadlines with clarity and empathy.
The member experience was updated to dynamically reflect any configuration the employer set up.
During the grace period members would be warned about changes to eligibility rules at multiple points in the member journey.
When a member attempted to submit outside the configured window, the product no longer blocked them. Instead, it sent their application into a special queue that enabled Member Ops to have a record of their application in case of future exception requests.
3. Augmented Member Ops Tools
We augmented operations workflows to support the new system without increasing burden.
Ops agents could view configuration details inline, so they understood employer-specific rules at a glance.
Exception handling became easier: if a member secured an exception from the employer, the Member Ops team had access to the member’s original submission rather than starting from scratch.
This reduced back-and-forth and manual and gave Ops more confidence in the accuracy of their case data.
Together, these solutions transformed Tuition Reimbursement from a reactive product into a predictable, configurable benefit that better aligned to employer and member interest without causing a spike in Member Ops workloads.
Results
The redesigned TR benefit positioned Guild to scale Tuition Reimbursement more sustainably. The results of this initiative have a long tail but the initial indicators all point in the right direction.
Adoption: Several key employers agreed to adopt at the start of their benefit year and more employer adoption conversations are ongoing. Newly signed customers launched with the new functionality on day one of their benefit.
Operational Efficiency: Ops measured no decrease in time-to-resolution or increase in volume despite the new workflows and member experience.
Member Impact: We measured an initial increase in the proportion of members who proactively confirmed their program was reimbursable before going out of pocket. In interactions with Ops teams, members reported more confidence in their understanding and ability to use the benefit.
Business Value: Customer Success and Sales teams were able to position TR as a more controlled, predictable benefit, strengthening employer trust in Guild’s platform.