Project Overview

Project title
Checkfront Memberships

People involved
  1. Product Team - Myself as the lead designer, 7 developers, Product Owner, Product Management.
  2. Marketing - For launch related activities and copy editing.
  3. Sales - For ongoing customer acquisition.

Timeline
  • 1 month research (September 2023)
  • 4 months in development (November 2023 - February 2024)
  • 3 milestones of fully functional Memberships
  • Note that we could have delivered this earlier but our project had staggered development timelines due to shifting priorities

Impact
  • Successfully sold Memberships to sales deals with clients, increasing Checkfront's revenue
  • Provided a new avenue for customer revenue generation, enhancing client profitability and satisfaction
  • Made Checkfront more competitive
  • Retained accounts on the verge of churning, increasing loyalty
  • Achieved early rollout of features despite changing priorities and business strategy pivots
  • Our team demonstrated strategic delivery, delivering value to the stakeholders, the business, and our customers while navigating scope reductions
  • Fixed usability issues in the pages that touched by this project, as a way to fix ongoing UX debt in areas like setting up the discount, setting up a product, and the accounts page.

Medium to enterprise customers wanted more money, loyal customers, and different reward systems, the answer: Memberships

Checkfront is a business for allowing people to sell experiences using a booking software that manages customer's booking, inventory, reporting, messaging, and web hosting in one centralized tool. It has a recurring revenue of $15 M handling more than $1 B in booking revenue volume.

Project duration: Constantly changing

We started researching on September 30, 2023, but it did not go into development until November 2023.

We had 1 month to research, ideate and develop a release plan, technical implementation plan, and design direction. We had 4 months to release a project in three milestones.

Note: Memberships needed to be delivered while I was working on three other projects. The deadline kept changing, and kept getting shorter and shorter.

We wanted to see how many people used it, and if they were making money from it

Increase the amount of recurring active users
Increase the amount of revenue for our customers
Offer exclusive membership benefits to members
Track feature use and adoption rates

Triple Diamond Methodology

I relied on a triple diamond process our product design team at Checkfront created and all the activities under this list was used to deliver this project successfully.
Research
  1. Competitive research - I had to understand what Checkfront's direct and indirect competitors were doing.
  2. User research - As the PM/POs conducted user research, I categorized them in Dovetail to see what insights we could gain from the interviews.
  3. Unmoderated card sorting exercise - Using Useberry, I conducted an unmoderated card sorting exercise for navigation. Memberships will be a new feature in Checkfront, and we wanted to make sure they were easy to find, so we tested where best to include this in the navigation.

Define
  1. Affinity Mapping Session - The team needed a shared context of the research conducted, and we needed to isolate ideas that we wanted to work on that our product could actually support.
  2. Dot voting for priorities - Senior developers, myself, and the product manager went through an exercise to vote on the highest list of priorities that we should have as a team.
  3. User story mapping - With the same team, we began to craft user stories into separate release cycles.
  4. Glossary of terms - Checkfront is slowly improving at creating standardized terminologies across developers, designers, technical writers, and copy shared with our customers. So, we crafted a glossary that the team could use to refer to the new things we were going to create.
  5. Collaborative design sessions - There was a lot of back-and-forth between design and development regarding priorities, but it allowed us to have a smoother start before the project commenced.

Ideate
  1. User flows - I created userflows for each milestone.
  2. Created Lo-Fi to High-Fi mockups - Creating the mockups was easier when the User Flows were approved. Since this project wanted to prioritize speed, I had to sacrifice the level of detail when creating Memberships. I would take screenshots of existing pages and sometimes generate a patchwork mockup at the start.
  3. Stakeholder Reviews - We shared the progress within the team and outside the team with stakeholders weekly to prevent a mishap that happened early in the project when a team decision for a "design" that was made and approved by the team for a month was deemed unnecessary by Stakeholders.

Validate
  1. Prototyping - I created multiple prototypes to test the third milestone. We released the first two milestones in Checkfront Labs
  2. Validation - I had unmoderated and moderated usability testing for the prototypes that tested the following things: Discoverability, Membership settings, adding discounts, adding products, and adding membership pricing.

Consultation and collaboration
  1. Design process - I paired routinely with development to test designs to see if they were up to spec.

QA
  1. Design QA - I helped with the Bug bash, reviewed all the design scenarios and created about 30+ follow-up bug tickets. It was challenging to test memberships individually while the individual parts of the feature were being built. It was only when the feature was "put together" that we could actually start testing it.
  2. Copy QA - I worked with marketing to ensure that Memberships was copy-reviewed.

Post launch
  1. Feature gating - We've isolated the first round of users that tried this in Checkfront Labs and it's now a gated premium feature.
  2. Design support - As the design lead in this project, I am the main point of contact for any membership designs. I usually support the team when any new bugs or issues come up.
  3. Design backlog - During the design QA process, we've filled up possible action items that could further improve the Membership Experience.

Challenges and ways I solved them

Shorter timeline
💡 Challenge
Following the merger with Regiondo and Rezdy, our restructured priorities led to an accelerated timeline for completing Memberships.
🧡 Solution
I and the team efficiently delivered Memberships ahead of schedule, prioritizing core features during downtime amidst work on three other projects, ensuring we hit crucial project milestones.
Usability not a priority
💡 Challenge
With the new leadership, there was very little to no buying on doing further validation or testing.
🧡 Solution
Checkfront was becoming a feature factory and wanted speed over any usability improvements, however I was able to ask for some leeway when we still had time. So research can be done if it did not affect the scope or push back deadlines.
Lost valuable teammates
💡 Challenge
We lost two main product designers whose feedback was critical for ongoing critiques. Our team was reshuffled. Technical leads shifted. The company had new leadership, our PO and PM was supporting two teams.
🧡 Solution
We optimized user learnability by utilizing existing components. I focused on essential designs, collaborated closely with our developers, and conducted frequent design pairing with another designer in Checkfront, overseeing the journey from design to QA to guarantee quality.
Design pivot
💡 Challenge
Mid-project, we hit a snag when a key stakeholder’s feedback necessitated a design pivot, despite earlier approval, even with usability concerns highlighted by SUS survey results.
🧡 Solution
We decided to agree with the Stakeholder's assumption to reuse an existing component to save time on scope even if does not have good user experience especially around copy. I led a collaboration with Marketing to sharpen our messaging. I asked to do usability testing only on new patterns we are introducing.
Sister company dependencies
💡 Challenge
Another team’s integration efforts, rooted in Checkfront’s existing features, couldn’t encompass the expansive Memberships feature.
🧡 Solution
Checkfront Labs enabled immediate customer product testing. Our sales teams now leverage Memberships for new client acquisition, now exclusive to select clients. Feedback from this launch informed leadership’s next steps, which was to gate this Memberships as a premium feature.
Customer wishlist
💡 Challenge
There were some unmet customer demands:
  • Continuously Renewing Subscriptions
  • Guest/Customer-Facing Membership Page
  • Profile Photos for Customers
  • Punch Card Experience
🧡 Solution
We possess the necessary documentation for these features and will only proceed once we get customer feedback. Current priorities lie elsewhere.

My research found that over 70 of our customers wanted this, but a Membership plan can mean 20 different things for each person, so we had to narrow down our options

Many of our customers wanted memberships, and there more than 70 customer requests.
  • People often ask this when considering transitioning to Checkfront from a competitor.
  • Memberships are discussed in the public community forum of Checkfront with about 10 upvotes.
  • However, customers have different needs when they talk about Memberships, but here are some of the similarities:
    • It's a revenue generator because it encourages customers to return to their products. Companies want to reward repeat customers and track their habits.
    • Membership discounts are a primary need - the ability for their members to receive discounted rates for specific products.
    • Tiered Membership also came close. For example, a bronze, silver, and gold membership.
    • Members must have premium products that are only available to them or reserved availability for existing products. They must take priority over non-members.

Customers have different needs, but they all want more revenue and a way to provide VIP services for their loyal customers

Subscriptions, prepayment, season passes, class passes, and punch cards are the different types of memberships that people may need.
  • Some have staff who are the only ones booking for customers, while others want their customers to be able to book the products themselves.
  • Some wanted to see a photo ID and data tracking for members. They said it would be helpful to reward them, send them birthday gifts, and know when it's needed to upsell.
  • Another wanted a community, a way to talk to members and field them the correct information as the service.
  • Others wanted a subscription service, a way to take recurring revenue.

One of our direct competitors cannot provide a self-serve option in creating membership plans, so we saw this as a possible advantage

Fareharbor
  • You are able to create multiple memberships with different discount rates, indicate the type of customers (for example, child or adult) that can access the Membership, set which products it would apply to, and arrange several uses it can be applicable for.
  • A member would be provided with a membership ID (without a need to log in), and they could book that way, applying something that felt like a discount code.
  • We wanted to avoid going in this direction because the most common examples of Membership typically require someone to register for it.
Peek Pro
  • Members can enjoy the following perks: discounts, priority booking, and early access. Peek Pro offers punch cards, where a customer can purchase an activity at a discounted rate a limited number of times. They also have season passes, so people can do an activity an unlimited number of times during a specified season.

I wanted to figure out where should we place it on the navigation and the results were surprising

Card Sorting Resorts

I organized a card sorting survey involving both our customers and our internal team (affectionately known as ‘Goat’). The goal was to determine the optimal placement for the new ‘Membership’ menu once the feature went live. Additionally, I had previously worked on Staff Roles, although it was eventually excluded from the project scope.

The survey itself was conducted using Useberry.

I had to do 7+ workshop sessions to give my team a shared understanding around what we were building
Workshops I did were one to many, aside from the regular meetings with the product team and stakeholders. Some of the members of my team who never participated in these sessions were uncomfortable, but overall we needed clarity which is what these sessions are about.

  • Affinity mapping session - To understand the research.
  • How might we  - To see the most promising opportunities.
  • Dot voting - Helped prioritize our tasks.
  • Now Next Later - Estimate feature development time instead of our usual T-shirt sizing activities.
  • Glossary of terms - Discussion on how we wanted to call new feature functions, and a confluence document as a source of truth.
  • User story mapping - Gave us a high level overview of our three milestones.

User flows saved us time

I created userflows that informed our mockups. These are some of the key interactions in the app. Pairing with development, product owner, product manager, and other stakeholders was crucial during this process.

I collaborated with developers since day one to ensure that Memberships did not look like a Frankenstein design

Below, I've included a few of the low to high fidelity mock-ups that I used to clearly communicate to the product team and stakeholders what we were building and how we were getting there. In the past, the development team would normally receive high fidelity mock-ups from their designers, and in the interest of time, sometimes, I was just making boxes with copy.

I also had the product design team to start using a standardized template, so any designer can easily take a look at the product at a glance and support this project even when I'm not around.

We reused an existing feature as a base, but there are newer features that needed validation which I did through unmoderated usability tests

I evaluated four tasks using four prototypes. Although I can’t share detailed data due to privacy concerns (PII), I tested Pricing, Cancellation, and Activation of Memberships with customers. Overall, the experience was user-friendly with all tasks mostly either 100% task success or close to it. While some users deviated from the most direct path, most successfully navigated through the provided prototypes.

We also had a beta test with a few customers, and I also conducted a few moderated usability testing sessions which helped us iterate on copy

During testing, we focused on whether operators (our primary users) could set up Memberships.

The tests helped verify some of my initial concerns around the placement of where memberships needed to be set up. Further feature work was discouraged so I was happy to sneak in some minor content updates.

Memberships, after successfully being used during the beta testing phase is now available as a premium feature

Memberships has been available for beta and is now gated but here are a few screenshots that I can share. Please note that the customer information is completely fictional.

Memberships was a success, it launched ahead of schedule, helped reduce churn, increase customer acquisition as a premium feature, and allowed us to work on UX debt

✨ Early business deals that hinge on the launch of the Memberships program have been won by the sales team.
✨ Helped reduce churn for customers that required Memberships as a main need for their business.
✨ We were able to launch earlier despite de-prioritization of the feature.
✨ We confirmed the interest of our customers in this newly gated premium feature.
✨ We fixed UX debt of the existing pages that Memberships have touched.
✨ We started working more closely with stakeholders and are trying to identify critical dependencies globally between product teams.
Credits to Storyset for their vector illustrations that made this page look lot better.

Let's Talk

If any of my projects interest you, feel free to reach out! I can elaborate on them better on a call if you want.

I accept freelance work and charge on a per-project basis. I like taking on projects that give me a lot of creative freedom. I enjoy ones that help make the world a better place.

I typically respond to emails within two business days but if I'm busy, expect a reply within a week at most!