Problem
In 2023, I had the privilege of working with Roadsider®, a forward-thinking company in the towing industry. They approached me with a pressing challenge—the need to revitalize their web app to provide users with a significantly improved experience that would match their competitors in the industry.
For quick context, the B2B SaaS towing industry is quite small, with ~6 major competitors. Within those company options, the top 3 companies have around 90% market share. I think this is because towing software is very sticky. You have to register all your employees, set up custom rates (a LOT of them), connect GPS tracking devices, connect to an insurance carrier API, and more. It's a lot of effort and a big decision to choose a provider. That being said, convincing someone to switch providers is very difficult.
I was brought in to lead the second version of Roadsider's app. At the time I was brought in, Roadsider had already released an MVP. The MVP validated that there was interest amongst tow providers for a new and better product, but users would churn pretty much right away or after only a few weeks of product use.
Upon doing some initial research, users were missing a lot of advanced features for custom setups. This allowed the product to work really well for small providers (1-2 trucks), but made it almost impossible for enterprise operators (5+ trucks) to use the product.
This fact was a glaring obstacle to the Roadsider's potential.
Problem
In 2023, I had the privilege of working with Roadsider®, a forward-thinking company in the towing industry. They approached me with a pressing challenge—the need to revitalize their web app to provide users with a significantly improved experience that would match their competitors in the industry.
For quick context, the B2B SaaS towing industry is quite small, with ~6 major competitors. Within those company options, the top 3 companies have around 90% market share. I think this is because towing software is very sticky. You have to register all your employees, set up custom rates (a LOT of them), connect GPS tracking devices, connect to an insurance carrier API, and more. It's a lot of effort and a big decision to choose a provider. That being said, convincing someone to switch providers is very difficult.
I was brought in to lead the second version of Roadsider's app. At the time I was brought in, Roadsider had already released an MVP. The MVP validated that there was interest amongst tow providers for a new and better product, but users would churn pretty much right away or after only a few weeks of product use.
Upon doing some initial research, users were missing a lot of advanced features for custom setups. This allowed the product to work really well for small providers (1-2 trucks), but made it almost impossible for enterprise operators (5+ trucks) to use the product.
This fact was a glaring obstacle to the Roadsider's potential.
Problem
In 2023, I had the privilege of working with Roadsider®, a forward-thinking company in the towing industry. They approached me with a pressing challenge—the need to revitalize their web app to provide users with a significantly improved experience that would match their competitors in the industry.
For quick context, the B2B SaaS towing industry is quite small, with ~6 major competitors. Within those company options, the top 3 companies have around 90% market share. I think this is because towing software is very sticky. You have to register all your employees, set up custom rates (a LOT of them), connect GPS tracking devices, connect to an insurance carrier API, and more. It's a lot of effort and a big decision to choose a provider. That being said, convincing someone to switch providers is very difficult.
I was brought in to lead the second version of Roadsider's app. At the time I was brought in, Roadsider had already released an MVP. The MVP validated that there was interest amongst tow providers for a new and better product, but users would churn pretty much right away or after only a few weeks of product use.
Upon doing some initial research, users were missing a lot of advanced features for custom setups. This allowed the product to work really well for small providers (1-2 trucks), but made it almost impossible for enterprise operators (5+ trucks) to use the product.
This fact was a glaring obstacle to the Roadsider's potential.
First Steps
Above you'll see a look at the somewhat outdated interface. It's not terrible, but certainly not the most usable. That being said, I conducted some user surveys which showed that users were actually fairly pleased with Roadsider's aesthetics and branding. This informed my decision to do a refresh rather than a complete overhaul.
Next, I had to figure out why customers were interested, but ultimately decided to churn. I started with a deep dive into competitors, even asking a few trusted early users for their credentials to other platforms so I could do an in depth dive of comparing features and functionality. Ultimately, I ended this phase with a very strong idea of what I needed to accomplish to beat competitor value propositions and make sure that users found the best features, functionality, and performance at Roadsider.
After those user interviews and doing the bulk of my competitive research, I learned that the old design got a lot of things right:
Modern UI styling and aesthetics
Action button priorities (meaning that the action buttons often corresponded well to the most frequent actions a user needed to take on any given page).
Good balance of preview vs detail info.
But also got a lot of things wrong:
Deprioritized financial information. This is key to any towing business is to see how much each order is making for them in a clear, listed format. It helps verify order accuracy, which in turn ensures customers aren't over or under billed.
Wrong preview information. The preview information had the right balance of screen space, but often didn't have the important quick supplementary info that providers actually used in their workflows.
Lacking advanced features. Product was missing important features like License Plate Lookup (requires an integration with state DMVs), advanced rate customization, and more.
I then moved to organize critical feature discussions with the company's CTO and marketing officer, covering what was possible, what features they absolutely needed, and got their feedback on these initial ideas and research.
Roadmapping
Getting on the same page with relevant stakeholders was critical for this project.
Through organized meetings with the CTO, CEO, and marketing officer, I was able to craft a product vision with clear milestones, including key features Roadsider would develop and most importantly, why those features were being prioritized (backed by user and competitive research) and how that would set us apart from the competition.
That list included a revision to almost every single part of the platform. Some small tweaks, some major renovations, and some completely new pages and features entirely.
Now came the next, and arguably second most important step: making that product vision become a reality.
Technical Setup
Since the product was getting a UI update, the release timeline and technical methods had to become more nuanced to avoid releasing parts of the product that had a completely different UI style than the existing product. In collaboration with the CTO, we decided the best path forwards was to set up four different environments:
Production - the live product
Staging - the live product's next series of updates in testing
Update environment - dedicated to housing the work done on this update and would eventually become production
Investor Update - used to show progress to key stakeholders (primarily investors and very important users). Stable versions of the update environment were created as needed to make this version. It was also helpful for showing the CMO key new features we were working on and how they actually worked so they could leverage that information in an update awareness campaign.
These different environments would allow the current product to continue functioning while building out an entirely new product in it's own testing environment. From the product roadmap, each major feature was made it's own design initiative, and I worked with engineers in an agile format to submit "releases" to that update environment until the entire update was ready to move to production.
In addition, while the initial design phase was being completed (which would take a bit longer because of the inherent work of creating a new UI style), engineers were able to use the Roadmap and detailed structure document I provided to start doing backend work (which prevented engineers running into a huge roadblock and idling during the first design phase until they received an updated UI library).
The decision to create a new update environment instead of releasing directly to production helped us avoid releasing new UI style parts of the product Frankensteined together with an older UI style, but came at the cost of delaying users getting any new features. I offset this cost by including ample testing with designs and wireframes with real users, ensuring that what developers ended up with was a research backed, confident product.
Design Process
Here's some insight into my general process for approaching each feature during the design stage:
Discovery
Goal: Learn about this feature's history (if existing), what users liked and didn't like, and understand the team's goals for this feature. Loop in engineers early for feature estimates.
Research
Are competitors using any similar features? Are there any ideas worth investigating for this product?
PRD
Create a thorough and understandable PRD that summarizes hours of meeting context into one document with simple goals and context. Confirm plan with engineers.
Design
Collaborate with designer, assist in user testing, demo early versions to the team to make sure we're tracking in the right direction.
Review
Review the complete design with relevant stakeholders, collect feedback.
Test
Test with real users in the form of clickable prototypes or static mockups.
Implement Feedback
Final review
Repeat the process for all features!
Revamping Roadsider and accommodating all of the new features was a daunting task and a lot of work, but little by little we chipped away and kept on schedule while keeping the CEO, CTO, and investors in the loop of my progress with special access to the update environment.
