Squarespace Career Growth & Development

How do you structure mentorship and technical learning for engineers?

I believe strong mentorship and technical learning work best when a team has a balanced mix of experience. That creates clear opportunities for junior engineers to learn from more experienced teammates, while giving senior engineers meaningful opportunities to mentor and expand their impact. 

As engineers grow into more senior roles, I intentionally create mentorship opportunities for them. I believe mentorship is valuable for the mentor, not just the mentee. Teaching is one of the best ways to deepen your own understanding, reinforce good technical habits, and grow as a leader. On our team, mentorship often looks like having a dedicated person to go to for questions, onboarding support, pair programming or whiteboarding sessions, PR reviews, guidance on architecture docs and feedback on work breakdowns.

Beyond learning through execution, code review and iteration, we also make space for shared technical learning as a team. We have a weekly forum to talk through technical challenges, align on solutions, and share knowledge from recent work, whether that’s something new someone learned, a design decision worth discussing or lessons from something that did not go as planned.

What internal mobility or upskilling programs have you launched recently?

I really value creating an environment where engineers can grow in different directions over time. Internal mobility is an important part of that. At Squarespace, engineers have the flexibility to explore opportunities on other teams when there is a strong fit, and managers work together to make those transitions as seamless as possible.

On the upskilling side, a major recent focus has been helping engineers thoughtfully incorporate AI into their day-to-day work. We’ve encouraged experimentation with new tools as part of the development workflow and created space for engineers to share what’s working, what isn’t and where these tools are most effective. That shared learning has helped the team build fluency quickly while also being intentional about where AI adds real value. I believe upskilling works best when it is built into everyday team culture rather than treated as a separate activity.

How do you identify and support future technical leaders?

In my experience, future technical leaders are usually the people the rest of the team already trusts and naturally looks to. They are strong in their domain knowledge and consistently deliver high-quality work, but what really sets them apart is how they elevate the people around them. These are the people who are always lending a hand, giving actionable feedback, improving team processes and proactively sharing knowledge. They also tend to be strong communicators, keeping stakeholders informed, surfacing blockers early and, most importantly, creating space for different voices on the team to be heard.

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.

Squarespace supports career growth by giving employees opportunities to move across teams, build new technical skills and align their work with long-term professional goals. Engineers can deepen their expertise while gaining exposure to different technologies and challenges, with resources such as peer coaching and employee resource groups providing additional guidance and development support.

“Squarespace has supported that growth through internal mobility. Being able to move into other teams gave me exposure to new technologies and challenges that align more closely with my long-term goals.”
 

What’s the career growth like on the customer success or customer experience team at your company?

On the customer success team at Squarespace, career development is uniquely dynamic because it isn’t limited to a single specialization. As the customer success manager role continues to evolve across the industry, adaptability is key to meaningful career progression. Instead of a narrow path, customer success managers develop a broad skill set that creates natural stepping stones into customer success leadership, product, solutions engineering, sales and operations. 

On a daily basis, customer success managers collaborate with these teams while gaining firsthand experience in how our customers run their businesses. Through that exposure, customer success managers develop essential skills in business strategy, technical problem-solving, data analysis and cross-functional stakeholder management. Understanding how all these moving parts fit together prepares customer success managers for long-term growth both within customer success and beyond.
 

What training or learning resources help team members build product and customer expertise?

Our customer success team learns through a combination of structured onboarding, product training and self-serve learning paths. Customer success managers use product deep dives, enablement one-pagers, internal knowledge bases and playbooks to build confidence across Squarespace’s products and customer use cases. 

The team also benefits from onboarding buddies, coaching, peer knowledge-sharing and direct partnership with product and customer operations. Those relationships help customer success managers connect product capabilities to real customer goals, while customer conversations and feedback loops continuously deepen their expertise.
 

What should candidates know about the skills they can develop in this function?

Candidates should know that customer success builds a surprisingly broad skill set that goes well beyond product expertise. You learn how to understand a customer’s business model, identify risks and connect product capabilities to measurable outcomes like retention and growth.

You also build strong stakeholder management and cross-functional collaboration skills. Customer success managers work closely with internal partners like product, sales, marketing and engineering, giving you a clear view of how a company operates. As a result, you develop the ability to build alignment, influence without authority and serve as a trusted business advisor rather than just a product expert.