Sishir Mohan, a product manager at Squarespace.
Sishir Mohan, a product manager at Squarespace.
| Courtesy of Sishir Mohan

Before Sishir Mohan was a product manager at Squarespace, he was a customer, using the platform to create an online portfolio of his side projects. His goal was to change careers from engineering to product, and he needed a website to help him do it.

“When I chose to make the pivot in 2017, I had to demonstrate to companies that I had product skills,” he says. “The portfolio showcased my side projects that I built as an engineer but thought through like a PM. I loved that there were so many great templates on Squarespace, which allowed me to focus on the content of my portfolio rather than how it looked. That made my life easier, and I was able to apply for product positions right away.”

Flash forward to 2021, and Mohan was job hunting once again. “I started to update my portfolio and I realized that I should apply to Squarespace!” he says. After reading articles about the company’s growth and employees’ positive experiences, he adds, “it was a no-brainer for me to apply.”

Today, Mohan works as the growth PM on Unfold—a Squarespace app that helps individuals and brands capture audiences on and monetize social media—focusing on increasing the number of new trials and subscribers.

Here, he shares how he got a job offer at Squarespace in less than a week, why the company encourages employees to pursue passion projects, and how working at a startup can do wonders for a career in product management.

Tell us about your career journey. What inspired you to pursue a career in product management?

I started out as a software engineer. I really enjoyed studying computer science in undergrad and grad school, and then joined Sumitomo Mitsui right after. During my time there, I found myself constantly concerned with “why” we were building something and less about “how” it was being built. That’s where my mind naturally sat. I was always thinking about the end user and how the web app we were building would be used.

What transferable skills do you currently use from your time as an engineer?

My engineering background allows me to evaluate the effort and impact that come with certain design decisions, and I use that skill on a daily basis when evaluating product features. I am also very much an engineer’s PM. I like to sit in on technical refinement meetings where we pick apart a feature we want to build. This in turn enables me to communicate difficult engineering blockers that make it easy for stakeholders to understand, so that they feel confident in my decision to shift priorities when needed.

How did you know Squarespace would be a good fit?

The ethos of the company around empowering creators and entrepreneurs fit perfectly with what I wanted to work on. I enjoyed the Squarespace product because it empowered me to build a portfolio, which in turn made my job pivot much easier than it otherwise would’ve been. So once I found a match with Squarespace’s goals as a company, it was just about the people I spoke with during the interview process. Everyone I talked to had only great things to say about working at Squarespace, and they were all so genuine, too.

What was the interview process and onboarding experience like at Squarespace?

The interview process was so quick and smooth. I had a phone call on a Monday with a recruiter and I revealed to her that I wanted to work at Squarespace despite having a couple of other offers on the table. She expedited me straight to an on-site, and by the end of the week, I knew I would be a Squarespace employee!

During the process, I spoke with product leaders who gave me the time and attention to ask questions, and they painted an honest picture of what it would be like at Squarespace. I met with quite a few people who had been at the company for four-plus years. It was encouraging to see that the company retention was high.

I was also allowed to explore Unfold, a subsidiary of the organization, as an option. It was something I mentioned to my recruiter and she set up meetings with the Unfold and Squarespace teams so I could determine the best fit for me.

How has your experience as a Squarespace customer impacted your experience as an employee at the company? And in what ways does Squarespace encourage employees to use its own products and services?

One thing I appreciate about being an employee at Squarespace is being more aware of all the initiatives across the organization. When we do big internal presentations like Hack Week, Design Week, or even all-hands meetings, we learn more about the great products that Squarespace is building or improving. And as a customer, I start to really think about how I can expand my goals in my personal passions through the Squarespace platform. I look forward to the product improvements that I see come to fruition as an employee knowing that I’m making a positive impact on other customers like me.

I was so surprised to find out that Squarespace encourages employees to have passion projects because my perception of most companies is that they want their employees to just focus on their job. I also love that we talk about and share our passion projects at work, too. I really value this because it helps me get closer to my coworkers.

What skills are necessary to succeed in your role and why?

I work with multiple teams, from CRM to marketers who run paid acquisition to design and engineering. All of these teams work on the same initiative at a given time, which means I need to have a bird’s-eye view of what we’re doing and also be detailed enough to point out edge cases.

When chatting with engineers, it’s important to really know what you’re talking about and ask the right questions. When chatting with other teams, it’s important to communicate timelines and any blockers as clearly as possible.

What lessons did you learn as an app founder and how do you apply them in your current role?

The truth is, you don’t really know which feature is going to work. Data and customer insights can give you ammo to convince stakeholders or help you make an educated guess, but it might still fall flat. So I typically go back to a couple of questions that I think are important: Can we build an MVP of the feature? And if so, can we test it? Depending heavily on the answer to those two questions, I tend to determine the prioritization for what we build.

What are you working on right now that excites and inspires you?

Creators have changed in the last couple of years with the advent of TikTok, and working on making Unfold a major player in the video space is so exciting. Unfold has such a strong reputation as a story template app, so I’m really keen on building features that position it to compete and win in the video app space.

What is the biggest challenge you’ve faced in your career and how did you overcome it?

Pivoting from engineering to product took much longer than expected. I thought that having the engineering background would allow me to fall easily into a product role, but I realized I was usually going up against more experienced product professionals during the interviews. It took months of freelancing and trying to gain the necessary experience so that I could tell the story about the product work I had done and the impact of that work before I was able to land my first full-time role as a product manager.

What advice do you have for those pursuing a career in product?

If you’re struggling to find opportunities to get experience under your belt, I strongly encourage creating experience by doing a personal project. It’s a great way to understand all aspects of a product, from ideation to execution.

It’s also important to have people who believe in you before you’ve proven anything. This is where networking comes in, but it’s also about articulating your passion for a product and convincing others that you’re willing to do whatever it takes.

This attitude comes especially handy at startups, which is where I recommend everyone pursue their first product opportunity. Startups care less about your past experience and more about your willingness to get things done and figure things out. And the best part is that you’ll start shipping features immediately at startups, so you’ll quickly learn how to be a product manager. In my opinion, one year at a small-yet-growing startup equals five years at a larger organization.

What’s your go-to activity to unwind after work these days? What are you currently reading, watching, and listening to?

It’s always the best time of year when both the NFL and NBA are in action. I’m watching a lot of sports, rooting for the Vikings and Cardinals because I grew up in Minnesota and Arizona. I’ve gotten heavily into sports betting so that is really fun. But I’m being responsible! At any given time I’m either watching sports, listening to sports podcasts, or thinking about what to bet on.

Updated 10/14/2022