The Importance of Feedback, Curiosity, and Confidence — Advice From an Engineering Manager

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Jackie Benowitz

Photo courtesy of Squarespace.

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If you’re interested in growing a career in engineering, Jackie Benowitz, an engineering manager for the Digital Products & Services group within Commerce at Squarespace, has some key advice for you.

“Be curious,” says Benowitz. “Whether that’s understanding a decision, diving in deeper to new architecture, or getting to the bottom of a bug — you’ll learn something invaluable just by being curious.”

Another benefit of curiosity? Well, Benowitz shares how this trait can lead to leadership opportunities! “Curiosity allows you to ask the right questions to understand problems your team is facing or understand the impact and need of a technical design,” she tells us. “You’ll also be able to learn so much if you’re just curious about the systems in place and how they interact with one another.”

To grow your engineering career, Benowitz also emphasizes the importance of taking up space and having an opinion. “I don’t mean to be stubborn and unwilling to change,” she clarifies. “I mean do your research and come up with possible solutions to come to a decision. You’re smart and you have the ability, tools, and resources to come up with an educated decision. That said, allow for diversity of perspectives to change your mind! Sometimes, someone will have a perspective that you don’t, which will make you think differently — that’s great, too! This is a healthy conflict that you should get comfortable with as early as possible.”

In essence, as Benowitz shares, “being confident and humble is a hard balancing act, but is crucial for your own growth and development, as well as your ability to help others.”

For her own career journey in engineering, Benowitz followed this advice of being curious, confident, and humble. 

Before Squarespace, she previously worked in startups where her career fluctuated with the scope of the small business, and she found her curiosity and drive to grow not sated. She wanted more leadership opportunities —including, but not limited to, growing others, moving a larger team to a common goal, and optimizing process.

“I was getting bored solving only engineering problems after nearly a decade of doing so and at a smaller scale,” Benowitz explains. “I knew I wanted to learn both from a more expansive stack, but also how to move many more people toward a common goal.”

So, when an opportunity to join Squarespace arose, she knew she wanted to take it and grow herself. Now, at Squarespace, Benowitz manages two teams that strive to empower site owners to sell their content and build on the work of every other group at Squarespace.

“I’m currently focused on building out the strategy for the two teams and managing new leaders,” she explains to Fairygodboss. “My recent work has also included growing one team into two, managing a mix of independent contributors and managers, and transitioning from day to day execution to longer term outcomes.”

Here, we caught up with Benowitz to learn more about how her career has advanced at Squarespace, why she’s stuck around for three years thus far, and her advice for other women looking to move into leadership roles, too.

You’ve been at Squarespace for three years — congrats! What keeps you at the company?

The people! We have some of the brightest, most empathetic, and passionate people at Squarespace. It makes collaboration easy and enjoyable. For any problem that needs solving, there’s a person willing to help and/or listen if you need someone to bounce ideas off of.

The product is also a draw for me. I’m interested in empowering people who are trying to grow their own business, especially people who, five to ten years ago, wouldn’t have had the ability to do so on their own easily. It’s inspiring to see the positive impact we make on people, and how Squarespace can help them get their businesses and ideas up and running quickly, while not compromising on design in the process.

A lot of people believe that developing your career means changing companies, and not infrequently. What has enabled you to develop/advance your career at Squarespace?

Squarespace gave me the opportunity and flexibility to experiment between being a manager and being an individual contributor. 

I took a Team Lead role here within four months of starting, managing five people with a project that was still getting its sealegs. When I felt overwhelmed, I easily found support in my managers, peers, and team members. When I wanted to dip my toe back into coding and architecting, I had their support in reintroducing this work on top of my people management responsibilities in order to find a balance that worked for me. 

Furthermore, Squarespace allows people the flexibility to explore both independent contributor and management roles, so no decision ever felt final to me. There are a handful of people who have switched between staff/principal and management, paving the way to make it easier for anyone later on. If someone is interested in trying their hand at management, they can do so and easily switch back if they find it’s not for them. Similarly, if someone wants to tackle a problem from the role of a staff/principal engineer, they’ll encounter little red tape.

Managing people is not easy. How has Squarespace helped set you up for success?

Squarespace fosters a sense of community and humility. This is clear with the breadth and depth of self-run forums and groups within the company, one of which is our engineering manager forum that Dan Na discusses in a blog post here. I’ve also found two peer groups at the start of my career at Squarespace to help guide my own growth:

  1. The first peer group was a set of early leaders who went through manager training together. We met consistently and, whenever we faced challenges, we had each other to lend a friendly ear and at times feedback. 

  2. The second was a bootstrapped book club composed of various senior leaders who got together to read and discuss books on management. This group of empathetic leaders all wanted to grow themselves and help grow those around them. I was able to talk about real problems and get real feedback from smart people I trusted. 

Through these groups, I never felt alone. There’s a common saying that management is very lonely, but having these people around that wouldn’t judge and wouldn’t be in competition with me was incredibly impactful. As a previous manager once said, management is pushing code straight to production without test cases. These groups became my test cases, my retros, and my pager duty. 

Recently, I’ve also been involved in a Leadership Accelerator program. This cohort of 20 leaders across the company takes courses, gets coaches, and does a project together. So far, we’ve learned our leadership styles, started working on our leadership values and mission statements, and even did some improv! I’ve already learned a lot about myself, how I can be a better coach, and react in stressful situations.

What’s been your most valuable career mistake?

I learned a lot from not giving enough direct feedback, and not giving it early enough. When I first started management, I incorrectly saw feedback as criticism, and therefore avoided it. As I have grown more comfortable with managing, I’ve discovered that feedback is an extremely useful tool for both my direct reports and for me. I read somewhere that feedback is a gift that demonstrates your involvement and investment in someone’s career; it’s a good thing and helps aid their growth! That advice has been invaluable to me. 

It’s a lot easier to share the skills and focus areas you feel someone needs to work on up front, than to let that person believe they’re on track, only to be disappointed come promotion time.

What’s the one career move you’ve made that you’re most proud of? 

It’s a strong tie for me. First, as someone in Product Engineering, I get to see a release of a product and its direct impact on people. In that sense, watching both Member Areas and the native video hosting project, Video Collection, release successfully has been incredible to be a part of. We have such strong people on our teams, and seeing them work toward a finish line is always inspiring

In a similar vein, I’m always in awe of seeing people grow. Whether that’s seeing a new engineer start to put the pieces together and be able to autonomously deliver code, or seeing a new leader step up and guide their team to success — it’s inspiring to watch people discover and fully leverage their own strengths. Being even a small part of their progress makes me proud of the growth they’ve achieved, as well as the impact they’ve been able to drive for their team and for the company.

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