Squarespace Leadership & Management

Updated on August 31, 2026

Squarespace Employee Perspectives

Squarespace develops future technical leaders by tailoring opportunities to employees’ goals and giving them meaningful ways to practice leadership. That can include owning cross-functional initiatives, mentoring teammates or stepping into team lead responsibilities, with clear feedback helping employees turn stretch assignments into practical leadership experience.

“To support future technical leaders on the team, I focus on understanding where they want to grow and making sure they have the right opportunities to get there. That might mean giving them ownership of a large cross-functional initiative, creating opportunities to mentor others or supporting them in a team lead capacity if they are interested in management. The key is pairing clear feedback with intentional stretch opportunities so they can build leadership skills through real experience.”
 

Amanda Jensen
Amanda Jensen, Software Engineering Manager

Squarespace Employee Reviews

My days are usually split between weekly one-on-ones with my team and pockets of time where I can focus on what I need to get done for the week. The dedicated time to speak one on one with my team is the best place for me to hear about their wins, understand and coach them through their challenges, and help them move forward.
 

Employee Image
Trish Craine, Director of Operations, Engineering
Trish Craine, Director of Operations, Engineering

What People Are Saying About Squarespace

  • Strategic Vision & Planning: Leadership has codified a clear growth playbook—“Attach, Stack, Scale”—and reinforced it through the 2025 Refresh that prioritizes AI‑assisted creation, stronger Domains, and integrated commerce. Portfolio simplification, including the Tock sale, further concentrates resources on a coherent core platform direction.
  • Decisive Leadership: Portfolio moves like selling Tock and executing a take‑private with Permira, alongside canceling a planned Investor Day to reflect the new path, show willingness to act quickly in service of long‑term focus. Founder Anthony Casalena’s rollover and continued tenure signal commitment to the chosen course.
  • Collaborative & Aligned Leadership: The organization explicitly unites Product, Design, and Engineering under a shared vision with the founder‑CEO and President Kevin Doerr leading strategy and execution. This structure is presented as aligning teams around the platform roadmap and accelerating delivery.

Squarespace's Benefits

Hosts in-person all-hands meetings

Implements team-based strategic planning

Open office floor plan to encourage communication and collaboration

Uses an OKR operational model to clearly define goals and priorities