Ever experienced that moment when the company you've known since its scrappy startup days hits its awkward teenage phase? For Buildertrend, that moment arrived in 2024, and the unmistakable pimple on its face goes by the name of design debt.

After 18 years in the game, the core BT product has more quirky characters than a high school yearbook, and our customers are growing up faster than we are. As Buildertrend aspires to fortify its position in the residential homebuilder market, customers' patience is thin. This is evident in the resounding Net Promoter Score (NPS) feedback of 2023— every response highlighted usability issues that users are increasingly unable or unwilling to work around.

As a senior product designer, I see this as a challenge and a golden opportunity. This isn't just a tale of maturing software; it's a narrative of personal evolution. In this 8-minute read, I'm breaking down how I answered the call to action from the Director of Product Design to craft and pitch a pragmatic battle plan to tackle design debt in my focus area.

From training wheels to bicycle

To understand how I tackled the issue of cleaning up design debt in Financial Services, it's essential to know how Buildertrend got to its current state. The company used scrappy practices in the early days to gain ground quickly. They hired key contributors who could cover many bases and made fast moves to stake out the untapped homebuilding market. At the time, Buildertrend was the only software supporting residential homebuilders, so it didn't need to be perfect. However, as the company grew, it became apparent that its aging tech stack, outdated design, and complicated workflows no longer met its customers' high standards. Our users are no longer the stereotypical 'Chuck in a truck' builders transitioning from pen & paper to their first digital solution; they are younger, fresher to the field, and accustomed to polished online experiences.

In 2023, our in-house research and data team extensively researched our customers' experiences. We reviewed the insights collected from NPS surveys, user tests, and interviews with churned customers. The results showed that the overall friction of poor experiences was a much bigger problem than the lack of any discrete feature or capability:

"I have used this program for almost 3 years and have never seen a useful update. Each update has made operations on our end more difficult and less efficient. Is this done on purpose?" – Accountant, established general contractor
"BT seems to stand for big tech. Only worried about profits and product development to increase users not user experience. . ." – Designer, established general contractor
"Application is hard to navigate, Key functions and features are missing. Spend more time trying to figure out how to use the app rather than putting it to work for the team." – Company owner, established general contractor
"The cost keeps going up and the product keeps getting more complex, but what I really need in life is more simplicity." – Company owner, established general contractor

Buildertrend has consistently maintained an NPS score of around 13, with the SaaS industry average being 31. The product design team, led by our Director of Product Design, has long suspected that a focused effort to clean up almost two decades of accrued design debt would yield a more significant boost to feature-specific Customer Satisfaction Scores (CSAT) and overall NPS than introducing net-new features. The research revelations in 2023 created the opportunity to test this theory, so all I needed to do was define actionable steps to lead my cross-functional team to success.

Crafting a persuasive pitch

I work on two cross-functional teams that combine the expertise of product managers, designers, developers, and quality assurance analysts to set a strategy that maximizes both business potential and customer outcomes. From the start, I knew I would need to tailor my pitch to appeal to diverse perspectives. I defined three goals for my pitch:

It needed to include accessible artifacts to help any stakeholder make snap decisions about the potential impact
It needed to emphasize the low-effort, high-reward nature of design debt cleanup work
It needed to define measurable outcomes that would excite and motivate every member of the team

Developing the visual aids

I started by developing a visual model to educate my team about usability principles and help them analyze problems they encountered daily. The Usability Hierarchy of Needs was adapted by the Director of Product Design from Maslow's Hierarchy of Needs; the critical component of this pyramid says that to attain a higher level of satisfaction, the solution must first fully cover the more basic needs. I iterated on her diagram by including a quality attribute scale developed by Adam Erickson, senior architect at DMSi, who recognized that "our brains are good at matching patterns and making predictions, and the best products capitalize on that." This scale helps more technically-minded stakeholders relate to how users learn and anticipate patterns in digital experiences.

The design debt narrative begins with recognizing that most of the software's design debt exists in the pyramid's 'functional' and 'usable' levels. Users regularly report friction for small changes like movement or visual changes to buttons and other UI components, indicating that those adjustments have disrupted their memorized workflows. This buildup of friction results in what the Director calls 'The Chasm' between usable and intuitive software--- she posits that our company's outcomes are fundamentally misaligned with our current capabilities. We will not be able to deliver intuitive experiences when our users are still experiencing gaps in basic functionality and usability.

Once my teammates understood the scope and user impact of our current situation, I needed to give them the tools to evaluate and prioritize the design debt issues they found in our area of ownership. The next artifact I created was a severity scale. My first iteration was simple, with a single axis defining the affected level of the usability hierarchy of needs.

My assumption was that a simpler scale would empower individuals to quickly and intuitively assign a rating to items in our backlog. I wanted to ensure we spent most of our time fixing the problems, not cataloging them. However, the first scale was too ambiguous to be really useful. To make the scale more familiar, I referenced Buildertrend's biaxial bug matrix, which evaluates bugs against customer impact and exposure. My second iteration plots issues against a Pareto principle-inspired discoverability scale and the impacted tier of the needs pyramid.

This iteration had the desired result of helping team members make independent, confident decisions when adding design debt to the backlog.

Defining risk and reward

In 2023, Buildertrend's Product & Engineering teams moved from an older waterfall process to a more modern Agile framework. The two teams I support use Scrum methodology, and the devs can provide pretty accurate Scientific Wild Ass Guesses (SWAGs) about how many story points a given solution would require to finish. I know from experience that most design debt issues are simple; one dev can develop a solution in hours or days. One of the most persuasive elements of my pitch was comparing the low estimated effort of fixing issues to the relatively high severity score. Pointing out the low resource need helped convince the business-minded stakeholders, and showing the potential improvement to our velocity by including small user stories in our sprints was appealing to the tech-minded folks. This helped define our initial prioritization process; we chose to use the Weighted Shortest Job First (WSJF) model.

Setting SMARTER goals

To round out my pitch, I needed to align my team's leadership around some sort of achievable proof of concept. I had no delusions that design debt built up over nearly two decades would be cleaned up in one year, and this initiative needed to hold its own against other business priorities. When I finally made my pitch to the Group Product Manager, Scrum Master, and Application Development Manager, I asked for the latitude to do two things:

A comprehensive audit of all of our core FinServ workflows for design debt issues across the severity matrix, documented with user stories and visual references in a backlog in Asana, by the end of Q1
Clean up all 'major' severity design debt issues in those core workflows by the end of 2024

Admittedly, defining a cleanup outcome was a bit of a gamble before I fully understood the scope and severity of the design debt problem in Financial Services. Still, I knew I would only get this group's attention once during the foundational planning stages for 2024, so I took the risk and assumed personal responsibility for these metrics. I haven't laid out the specifics here, but I defined my goals in Asana using the SMARTER model, ensuring that each had a palatable amount of specificity, measurability, actionability, risk, timeliness, excitement, and relevance. I then used Asana's project capabilities to create a dashboard to track my progress and connected my goal to the parent goal owned by the Director of Product Design to solidify the link from the micro to the macro level.

Response & lessons learned

Crafting and delivering this pitch is one of the most demanding challenges I've tackled in my five-year design career. Though I've dabbled in strategic thinking and systems design under the eye of more experienced mentors, I've never had to persuade a group of cross-departmental leaders to change the direction of their yearly plan to accommodate a design-driven initiative. It is one thing to chase an ideal of customer-centricity and an entirely different beast to prioritize the less flashy work over apparent revenue gain.

My proposal received a positive response from colleagues due to established trustworthy relationships. Convincing executives to reduce capacity for an "underdog" initiative was challenging, but I persisted and won a tentative team-level commitment and time to conduct pilots with my teams. I've selected design debt items for each Scrum team and placed them in the next sprint. I look forward to seeing the results in our sprint review and moving forward with the audit at scale.

Looking back, I realize that I could have adjusted my presentation style to better fit the preferences of my audience. I received feedback that the higher-ups in the company did not have enough time to listen to the entire backstory behind the usability problem. While I prefer to focus on the qualitative aspects that affect customers' emotional response to the product, business and technical leaders can achieve more with less and would have understood the broader picture with just the quantitative data. Essentially, I worked harder than I needed to in order to get their approval.

As I wait to see how our pilots play out, I encourage other designers to leverage similar strategies to address institutional design debt in their focus areas and organizations. In the same way that the work can be low risk and high reward, the effort to build this pitch came naturally to me because the supporting data was already there. My Director of Design played a crucial role in setting the stage for me to make this pitch by priming division leadership to be receptive, and the researchers developed a consistent evaluation model to keep a pulse on customer sentiment. In a situation with less collaborative support, I imagine you could still successfully pitch a cleanup effort by conducting your own first-hand research and auditing your product for ‘quick wins’ that combine business and customer value.

This journey has taught me how to tell a compelling story and leap into the strategic hustle. I’ve taken away a new appreciation for the art of persuasion and the artifacts that prop up the story. Everything from the Usability Hierarchy of Needs to the severity matrix became pieces of a puzzle coming together into a bigger vision of stellar user experience. This cleanup initiative is Buildertrend's coming-of-age story--- the moment when our scrappy startup grows into its potential.

Musings

Bringing institutional design debt into focus