Project overview

Project title
Upgrades, Downgrades and Product and Pricing Strategy, also known as Repackaging

People involved
  1. Growth Product team - Myself as the lead designer, 2 developers, 1 senior developer, one product manager
  2. Marketing - Website manager, Copy editor, Marketing Executive
  3. Finance - Finance executive, and team
  4. Customer Success - Research for accounts and pricing
  5. Payments Product team - Similar sized product team in charge of shipping Checkfront Payments

Timeline
  • 4 months from January 2023 to April 2023

Impact
  • $1.3M revenue directly tied to repackaging for the first three months
  • Record high sign-up growth, highest it's ever been in 6 years
  • Helped with Checkfront's acquisition and merger deal with two other large booking software companies Regiondo and Rezdy
  • Optimized upgrade and downgrade flow, reducing finance and support costs and efforts related to manual chasing of payments and implementation of correct plan type features
  • Eliminated costly plan types that offered too many benefits to existing customers
  • Allowed Checkfront to charge at a higher market price, increasing revenue
  • Introduced Checkfront Payments as default payment method to free users, allowing Checkfront to charge per transaction made

The why behind the pricing strategy

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.
For a long time Checkfront knew that they were overcharging some of the pricing plans and underselling others. Checkfront was also lagging behind growth targets.

Project duration: A tight timeline

This project was going in the works for 3 years before it was handed over to my team for execution.

We had 4 months to complete the research and release the updates in an almost waterfall method. We successfully delivered the project within that timeframe.

Goals

Increase the amount of recurring active users
Increase the amount of revenue
Improve customer loyalty and reduce churn due to force upgrades
Make Checkfront more marketable to investors

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 how to make a successful Free Plan and ensure my team and Stakeholders knew what the risks are.
  2. Definition of Success - The data team collaborated with my team the metrics we wanted on a dashboard.
  3. Internal Stakeholder Interviews and Meetings - Researched on the problems, and what outcomes our Stakeholders wanted.. The drivers of the project was the Marketing team, the Sales team, and the Payments team. I scheduled individual meetings to outline their current workflows relevant to the project.
  4. Collaborative Design Sessions - Much of the research around the pricing project content was a joint effort between Marketing and myself. This meant weekly meeting updates with various stakeholders.

Design
  1. User flows - I created userflows for the current workflows, the current state of upgrade and dowgrade, and userflows for new features.
  2. Created high-Fi to mid-Fi mock-ups
  3. Creating reusable paywall templates - We created paywalls for features that should only be enjoyed by the two payment plans and made the template reusable so it was easy to scale for future projects.

Validate
  1. Prototyping - I created a prototype specifically for the downgrade process which was the only part of the flow that needed testing since it was 'new'.
  2. Validation - The part of the flow that needed to be smooth was upgrading and downgrading. I ensured we had time to test this at the very least internally with the customer facing teams and volunteers.
  3. Plan change - Another team in charge of handling the new plan transition conducted interviews with the existing client base and forecast the expected revenue loss and gains post launch.

Collaboration
  1. Ongoing Cross Department teamwork - I made myself available for consultation for various teams on how best to implement the plans page for the website, consultations with what data we need to track, what forms to add, and other new requests from the management or stakeholders that was within the scope of the project.
  2. Design approval - Synthesized and discussed the results of the research, and also got buy in for the designs we were choosing to implement. Where I could, I chose to delegate tasks that wasn't necessarily my forte and take advantage of the design team's ongoing design critiques to gather feedback from other designers.

QA
  1. Design QA
  2. Copy QA - Before the final release, I worked with marketing to create 100+ copy change requests focusing on plain and conversational language.

Pre launch
  1. Documentation - The design efforts, templates, research, and findings were clearly communicated to everyone in the company together with a large Q&A document.

Post launch
  1. Tracking metrics - The project would not be successful if we could not track the engagement, the number of users that were converting from the free plan, and the usage of Checkfront payments. Largely, the project was celebrated as a success.
  2. Design support - Tickets came up for support related to bugs that we did not catch in time, but this is normal. I continued to provide support for things we did not anticipate but they were mostly issues with payment terms in Stripe which is outside of my control. New paywalls needed to be created as well, to keep the managed plan competitive.

Challenges and how I got over them

Top down approach

💡 Challenge
This was a top down project that had a tight timeline.
🧡 Solution
We delivered what they wanted and what the company needed at that time.

Cannot test with customers

💡 Challenge
I had no buy in to test against actual customers because they did not want to fully announce the plans changing.
🧡 Solution
We had internal testing and ongoing critiques with the rest of the product design team. The research with competitors also helped us stick to best practices.

Freemium is not ideal

💡 Challenge
My research indicated that launching a freemium plan might be premature for us. We are better of with a demo-led approach, given the current usability challenges we face—despite the high learnability of our product.
🧡 Solution
Embracing the existing business decision was a strategic move, driven by our ambition to attract investors through the high-growth usage of our product. When we achieved this milestone, we refined our strategy. This involved streamlining our plan offerings and phasing out the freemium option, improving the revenue model and targeting better quality clients.

Too many stakeholders

💡 Challenge
We faced delays in resolving issues due to the many stakeholders in our project, with decisions taking up to two weeks.
🧡 Solution
While our team couldn’t make all the calls, we started weekly cross-team meetings to quicken decision-making. We focused on achievable tasks, met our deadlines, and the project was a success, meeting stakeholders’ financial goals. We’ve identified communication as a key area for improvement in future projects, and I’m playing a significant role in this initiative.

My research suggested Freemium is not a good idea, because of Checkfront's learning curve and considerable UX debt

I found out we either had to:
  • Option 1: Focus on making our experience really good if we go ahead with the free plan strategy, achieving exponential growth but risk not being as profitable.
  • Option 2: Go ahead with a demo led approach which suited powerful tools that took time to learn and implement.

Checkfront has problems in copy, having been initially created by developers without UX design oversight. Our research suggests consider Checkfront learnable but often it takes our clients over a year to master using the app if they are not tech savvy.

At the time, this project needed to attract investors, so despite the risks, we went ahead with launching a free plan with a focus on ensuring it was highly profitable.

Customers who downgraded and got automatically upgraded caused the billing team a LOT of headache

I've uncovered that our plan payment process from 2022 was incredibly manual. We had several problems that needed fixing.
  • We automatically upgraded people once they hit their booking threshold. Customers need to be manually downgraded when they complain.
  • The collective agreement was to stop this automatic upgrade, making some paywalls ineffective because they weren't being implemented.
  • Some customers were taking advantage of this. Support chased these accounts down.
  • It's easy to create new accounts, and it's also easy to upgrade as a customer. However, the downgrade flow, being very manual, was cumbersome for our staff because we let customers downgrade, but staff has to manually adjust customer plan limits.
  • Customers also often don't stick with the same email and account holder. Sometimes, the person who opens the Checkfront account is someone from the finance/tech department. When this person leaves, the actual account holder does not receive the payment reminders.

I was determined to ensure that the problems were solved.

Before: Signup page was difficult to navigate

  • I performed a thorough heuristic evaluation of the copy on the page and found:
    • Links were too close to each other.
    • Number of steps were not displayed.
    • No back buttons.
    • Unreadable text due to bad contrast.

After: Signup became easier to navigate with improved accessibility and better copy

  • New fields were added for marketing and sales.
  • Implemented accessibility enhancements which helps broaden market reach.
  • Showed number of steps to provide more clarity.
  • Better font hierarchy resulted in scannable content.

Before: Customers had to choose from 7 plan options, custom plans, and staff had highly manual workflows

❌ Before - We had 7+ Plans
  • We had too many plans
    • We offered a Trial Plan for those wanting to test our product before committing.
    • Subscription options - Pro, Plus, Soho, Enterprise, Flex, and Hibernation.
    • Custom plans were created by sales.
  • Problems with upgrades and downgrades
    • Assigning benefits to each plan is still manual.
    • The auto-upgrade function turned off = no plan limits = unlimited bookings and benefits for some customers.
    • Staff to actively monitor downgrades, manually adjust limits, and apply fines and fees to ensure compliance.
  • Pricing concerns
    • Our fees have remained unchanged for several years.
    • We wanted to find the right balance that supports both our customers and our business sustainability.

After: Reduced plans, standardized benefits, completely self-serve downgrade and upgrade experience

✅ After - Updated plans now easier to navigate and choose
  • We’ve refined our plan offerings from seven to just three, tailored to specific geolocations.
    • Below, you’ll find the newly introduced Starter Plan, Growth Plan, and Managed Plan.
    • We’ve phased out the older plans for new customers, paving a smoother path for self-directed upgrades when they’re ready to expand.
    • The plan page also had to be replicated in our website.
  • For our free users, Checkfront Payments is now the default payment method, which is a new source of revenue.

After: The new downgrade and upgrade flow removed the headache for the billing and support team for chasing payments and manually updating plan benefits, saving us extra dollars and time

✅ After - Upgrade and Downgrade Process
  • We’ve streamlined the downgrade process into four-steps that required no manual support because plan benefits applied.
  • Additionally, we’ve ensured clear communication throughout, so customers were well-informed about the features they'll be parting with at each step.
  • Upgrade and shifting from an old plan to new plans was also streamlined so customers with custom plans could now have standardized plans.

After: We tracked the best performing paywalls, and created a reusable template as a base for future paywalls

Before we updated our plans, the presence of paywalls was minimal since we relied on usage-based capping of our plans, such as the number of bookings and users. This meant there was no differentiation of premium features across the plans.
  • However, with the introduction of over 20 paywalls for premium plans, we’ve established a framework for future feature gating.
  • This change has also given us valuable insights into which paywalls are most effective at encouraging customers to upgrade.

After: Mobile responsiveness was prioritized for the entire project which is a big win!

  • All pages are mobile responsive or have mobile designs.
  • Because we can now use the MUI design system (an initiative I was part of), we decided to implement some of their components which also had mobile components.
  • The majority of Checkfront customers are desktop users, but we do have a small segment that sign up for Checkfront as mobile customers. We wanted to increase app adoption so mobile designs were a must.

Cross department teamwork established!


  • I optimized feedback requests with marketing .
  • We highlighted areas of improvement through a retrospective.
  • The growth team was broken up and reorganized after this project, but what we learned within this team was something all team members could share with their future teams.

This project achieved $1.3M in just 3 months, record high customer acquisition, Checkfront acquisition and merger deal with Rezdy and Regiondo, and provided data insights that will support future pricing strategy changes

Wins
✨ We grew our user base, hitting our record high signups since the past 6 years.
✨ We reduced churn for higher paying customers that could downgrade.
✨ Checkfront was able to negotiate an acquisition merger deal, and now merged with two other companies namely: Rezdy and Regiondo.
✨ Increased adoption for Checkfront Payments.
✨ Overall since implementation, the project generated 1.3M USD in related revenue in the first 3 months alone, and brought in more people to adopt Checkfront Payments, Checkfront, and upgrade.
✨ Solved the difficulty of manually chasing payments for people who downgraded and manually adjusting their plan type since we allowed them to downgrade right away but they kept all the benefits, reducing finance team's effort in managing customers.
✨ Solved the problem of customers getting automatically upgraded to the next plan when their plan hit their plan type limits, reducing customer support complaints.
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!