How Feedback and Iteration Shaped Our Successful Website Redesign | Cuppa.so

Hey everyone!

I wanted to share our journey of iterating on our website since we started our company. Looking back at our first design, I can't help but laugh—I have no idea what I was thinking back then! As an e-commerce agency, our first version was a simple template, and it showed.

Over the months, we continually refined our site based on invaluable feedback. We received great suggestions on everything from copywriting to design. The challenge was figuring out the right pace for these iterations. While we shipped product updates weekly, we wondered if the same frequency was necessary for our website, especially since our traffic was still growing.

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We eventually pivoted and had to overhaul everything—SEO, copywriting, images—you name it. This major shift meant we couldn’t maintain the weekly iteration schedule. So, we scrapped all the pages except the landing page and decided to build it up gradually as we gathered new information.

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Whenever we added new content, I would tweak the designs. We started with the essentials: an about us page, a pricing page, and slowly expanded. As we did demos and created LinkedIn content, our media assets grew, and we could enhance the website bit by bit. Instead of trying to do it all at once (which didn’t go well before), we focused on consistency and matching themes across all pages.

Here’s a great example of our blog—before and after the redesign.

And that’s been our process. I’m still iterating but also trusting this gradual approach, which is definitely less stressful. Thought I’d share with you all!

Some Lessons we learned when creating our website content:

Staying Close to Our Customers

One of the biggest lessons we’ve learned is the importance of staying close to our customers. From the early days to now, we prioritize direct interaction with our clients. Through 1:1 demos and regular check-ins, we understand which features they find most beneficial and why. This dialogue informs our copywriting, using their own words to enhance our messaging.

Our Iteration Process

To continuously refine our messaging and positioning, we actively engage with our existing users. Here’s a detailed look at our process:

1. Collecting Feedback Systematically - We don't rely on random or sporadic feedback. Instead, we’ve developed a system to collect feedback consistently and objectively. We ask a set of standard questions during client catch-ups and new customer setups to identify what works and where there might be confusion. Additionally, we ask customers to describe how Cuppa helps them and which features they use the most.
2. Analyzing the Feedback - We process the feedback using a mix of AI to extract key words and phrases, which we compile into a spreadsheet. By tracking how often certain words or phrases appear, we can formulate new ways to describe Cuppa.
3. Applying Feedback Strategically - Part of our sales process involves B2B cold outreach via LinkedIn and email. We A/B test cold outreach emails with our new copywriting and measure the effectiveness of our sequences, from open rates to reply rates and demo conversions.
4. Comparing Results - We compare the results of our new copy with the old copy to understand the impact of our changes. For example, our first tagline was:“No matter how big or small you are, Cuppa helps you streamline your team's workflow, so you can give every client the VIP treatment — and a great first impression.”Our new tagline is:“No matter the size of your team, Cuppa streamlines client and project management. From onboarding to project completion, keep your clients in the loop and your teams in sync.”‍
5. Iterating on New Features - We follow a similar process when launching new features. We test with a group of users, gather feedback through Zoom calls, and refine our messaging based on their input. By the time we launch a new feature to our mailing list, we’ve iterated enough to have a solid offering.

Continuous Learning

Feedback is a continuous process of learning and improving. We treat feedback as a valuable resource and a growth opportunity. We remain open-minded, curious, and humble when receiving feedback and strive to be respectful, constructive, and specific when providing feedback to others.

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Here's our current website:

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