Did the PM loop at Squarespace for a senior PM role on the commerce side. Sharing what I got because the PM interview content for Squarespace online is nearly nonexistent.
The loop was four rounds: one recruiter screen, two PM-specific interviews, and one cross-functional round with an engineer.
What the PM rounds actually asked:
Product sense questions were rooted in Squarespace's actual product. Not "design an elevator for blind users" type hypotheticals. More like: "One of our templates conversion rates dropped 15% month over month. Walk me through how you'd investigate and what you'd prioritize." Or: "How would you think about expanding our analytics offering for small business owners?"
They want you to know the product and have opinions about it. I used Squarespace for a side project so I could actually reference the product experience, and that mattered. If you haven't used it, use the free trial for a week before you interview.
The strategy question I got: "Small businesses have a lot of options now, Wix, Webflow, Shopify. How would you think about where Squarespace should focus for the next 18 months?"
Execution / delivery questions: "Tell me about a feature you shipped that underperformed. What did you learn?" They want intellectual honesty, not a success story with a bow on it.
The cross-functional round was with a senior engineer. They asked how I typically work with engineering, how I handle scope cuts, and how I communicate when technical complexity changes the roadmap. Very practical. No product design prompts in this round.
What they seem to value: Customer obsession (small business owners are a distinct demographic with real constraints), data-informed decisions but not paralysis, and someone who can work without a lot of top-down direction. The PM culture seemed fairly autonomous.
What I'd change about my prep: I should have studied more of their recent product launches and blog posts about their design philosophy. Some of the questions assumed familiarity I had to fake.