The Value of Learning:

Reflections on Five Years at Webflow

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At Webflow, employees who reach their 5-year anniversary are rewarded with a generous 5-week sabbatical to relax and reflect. Although I didn't have much planned for this time off, I made sure to prioritize a few activities. My wife and I enjoyed a 3-night stay in Vegas, marking our first international flight since the pandemic began. I did some reading, including titles such as Sherlock Holmes, Brave New World, and Empowered. I took the opportunity to organize my living space by moving shelves from my office to the living room and completing the construction of our bedroom closet. In between these activities I spent time reflecting on my career in software and this article is me trying to get it down in writing.

My first step into web development was in 2012 with a non-profit organization called the Town and Gown Association. I was volunteering with them when they expressed a need for a new website, and - despite my background in urban planning - I took on the challenge. While it was a "fake it until you make it" situation, I found the experience to be incredibly rewarding and decided to shift my career focus to software and tech. After completing the Town and Gown project, I worked with several friends and family members as clients, honing my skills and learning the basics of web development.

In late 2014, I designed my own website using Webflow and joined its vibrant community of creatives, builders, and freelancers. Looking back, I see this version of my site as a reflection of the awkward transition I was making from urban planner to business owner/freelancer. I enjoyed incorporating full-screen hero sections and fixed scrolling effects into the design. And I took great care in explaining to potential clients who I was and what made me different. While the site wasn't perfect, it effectively communicated that I was a solopreneur and helped me establish a professional online presence.

Front page of my website from 2014
2014 home page

Thanks to my website and active participation in the Webflow community, I generated leads for a wide range of clients, from jewelry stores to restaurants. I am incredibly grateful to these early clients for taking a chance on me. Through these projects, I gained valuable experience in contract negotiations, client management, effective communication, and web development, which all laid the foundation for where I am today.

A year later, in 2015, I decided that I wanted to shift the type of leads that my website was generating. While I enjoyed working with smaller clients, the short engagement times meant that I was in a constant cycle of building the site, handing it off, and wishing the client well. I wasn't getting the opportunity to measure the impact of my work. It was time for a redesign.

home page of my 2015 website, above the fold
2015 home page above the fold
2015 homepage below the fold
2015 home page below the fold

Instead of focusing on a "get to know me" landing page, I shifted the spotlight to the customer experience and their specific problem. I made it clear that a successful website involved a continuous cycle of strategy, launch, and improvement, and that there was much more to success than simply building a site. This change in content and design proved to be incredibly successful. I completed 25 short engagement projects in my first year as a web designer. In contrast, my new approach led to a deep-dive with four clients over the next two years. During this time, I had the opportunity to work with clients such as Shade, a company making wearable medical devices that detect UV exposure; and Cota, a company bringing data and analytics to cancer treatments. Working closely with their VPs of Marketing taught me the importance of asking the right questions to help define problems before jumping into solutions, as well as the need to coach executives on the benefits of iterative development. 

During the summer of 2017, I was active in the community teaching others how to work with clients using Webflow. From that show of dedication, patience and product knowledge I was contracted by Webflow as a Quality Specialist to help them bring new and critical capabilities to market. Though I had experience working on the web, joining the creators of the product I was using daily gave me a large dose of imposter syndrome. This insecurity was reflected in my website. I changed up the design to signal my new role and that I wasn’t available for client work anymore. 

2017 home page of my site
2017 home page

This was a “be back soon” sign in the window of my shop, while also stripping it of any interesting content. That is how my site remained for five years, until my sabbatical. 

Despite my imposter syndrome, when I started working at Webflow I expressed to Vlad Magdalin that if I passed on the opportunity to join the team responsible for making my business possible, I would be kicking myself in five years' time. Looking back now, I was right. And I wouldn’t change a thing. 

In reflecting back on my time, I've had the privilege of working alongside some of the best professionals in the industry, tackling complex problems in visual programming. I've gained invaluable experience in launching products including ecommerce, ecommerce discounts, CMS scale, and Logic. Throughout, I worked with my team to overcome challenges ranging from: team coordination, bug management, defining product requirements, stakeholder management, and team re-organizations. 

2023 home page of my website
2023 home page

When you look at the site today, you’ll notice that the underlying design direction hasn’t changed from the five-year old screenshot above. What’s changed are small improvements, focus, and content with purpose. It’s a reflection of where I’ve been and a toast to the next five years and all of the new things I’ll learn between now and then.