Business Goals

Adding Scheduling to the line-up broadened our position as a true multi-product company. New customers to Scheduling had high intent as their business was typically in the position to accept appointments, and exiting Scheduling customers were active daily users. We wanted to add a new starting point to our line-up, as well as encourage our existing business customers to try out this new product. It was also important that the business didn't do worse after the acquisition!

People Goals

We had to be cognizant that for 40+ of our colleagues joining Squarespace, this was going to be a big change. One day they were going about their daily business, and the next they were flying to New York for 2 weeks of onboarding. It’s likely they were unsure what would happen with their jobs, let alone the product they built. We knew the two products had to integrate, and we couldn’t apply the same practices to people, that we would for technology. On top of this, Acuity was 100% remote, whereas Squarespace was all on site.

About six months into the integration, I presented a case study to my design team about my learning and observations.

Product Goals

The scheduling product was the opposite of Squarespace in a lot of ways; plenty of color, a personable tone of voice, workarounds for everything; and primarily built in a waterfall process. For me, there were two things we needed to figure out:
1. How would we make this product look and feel like a Squarespace product?
2. What people, processes and tools did we need to succeed?

Process

The first part was easiest. I could study the product and figure out a phased approach for how we could iterate quickly, and prioritized tasks based on the number of people that would need to be involved crossed with the highest impact.

The second part I didn’t know what I was getting myself into. I naïvely expected that team would be excited to do things the way we did, but I was met with resistance. There was an overarching fear that any product change we made would hurt the business and disappoint existing customers. Process-wise, the team was used to making updates on the fly with no design input or leadership approvals. I was worried that with these two patterns going together, we were going to see very reactionary product development.

I got buy-in from stakeholders on the for my phased product integration strategy. Though I would be the only person representing Squarespace product in the day to day, working with Acuity’s PM, engineers and designer. We started from the beginning and established a working agreement for the team; how did people prefer to work; what tools were being used; how did we think about deadlines; where would feedback happen.

One of the biggest points of contention was design reviews. The team didn’t want to go through the many-rounds of approval that Squarespace designers followed, as it would slow them down. This was a difficult position for me, because coincidentally on the Squarespace side, I was helping to define even more process for our designers! We had to work out many middle zones where the team could still operate autonomously, but manage to not go rogue.

What would success look like?

A product that looked and felt like part of the eco-system, and employees that were completed folded in to the Squarespace way of working.

Results

The business expected that the product would take one year to be fully integrated. We managed to launch a total re-skin on the product in about a month, and full product integration in eight months. Everyday was different, we didn’t have a template that could translate from task to task. We are now about a year past the acquisition, and continue to tweak our style. The most important takeaway from this project has been to take time to understand what is important to the people you work with. In lieu of any formal process, that tends to draw out the list of negotiables and I could see where my attention would be best spent.

Why is this project important to me?

It was really difficult. When I took on this project, I was in conversations with my manager about working on a new area of the product. They said to me, we have just acquired this company and we are going to need somebody to “make their product like our product”. This blew my mind because I couldn’t immediately envision what the work would entail. In all the product areas I was currently working on, we had an idea of where that product would be in 6 months, 1 year, 2 years … but with this new segment, it was a total blank. I’m drawn towards ambiguous projects but this one offered new interpretations each day.