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Squarespace’s Jessica O’Connell on customer support as brand ambassadors

Editor’s note: We’re extending International Women’s Day throughout the month of March to celebrate women in support leadership in this 4-part interview series.

It sometimes happens that the right career finds you when you aren’t looking. Such was the case for Jessica O’Connell, director of Customer Operations at Squarespace, an NYC-based company and all-in-one platform that empowers anyone to create a website and manage their online presence.

O’Connell started out after college as a writer, penning articles for the Department of Education. That was fine, but she didn’t see a future for herself in writing research papers. Her next move was to go back to school for an MBA—and find a new way to make ends meet.

“I began my career like many of us in customer experience—on the phones in a contact center. I needed a stable job to help me pay my way through grad school and I never left,” she explained. “I love that we are able to personally impact so many people in our industry. We are brand ambassadors and able to influence our products by advocating for what our customers need most.”

Jessica O'Connell

O’Connell did earn her MBA, but it’s her ability to advocate for the customer that’s led to a career in customer experience that now spans more than 19 years and includes stints at HSBC, Capital One, and Kaiser Permanente. Here she shares more about the lessons in leadership and customer experience that she’s learned along the way.

Can you tell me more about your career journey between contact center phone agent and your role, and team, at Squarespace today?

In terms of career trajectory, I’ve held most roles in customer experience. I started as a front line advisor, and then moved into writing test scripts for software conversions, worked in Learning and Development, and held a number of leadership positions—from managing contact center strategy to workforce management to IT and telephony demand management. I’ve been at this a while. In the end, the more varied my experience has become, the better I understand the needs of the customer and the business.

"In the end, the more varied my experience has become, the better I understand the needs of the customer and the business." - Jessica O'Connell

Currently, I am a part of Squarespace’s Customer Operations department, where we focus on helping our customers with any inquiry—from billing questions to design help to general troubleshooting. I work with the Advisor team here in Portland and also manage our global Support Operations team. Support Operations is the equivalent of Workforce Management in most organizations, but at Squarespace we like to think of our role as business consultants, versus narrowing our scope to scheduling and forecasting.

What are the most rewarding and challenging aspects of your role?

Helping someone turn a job into a career is the most meaningful part of the role for me, and it’s one of the primary reasons I joined Squarespace. In the years previous to my current role, I managed teams as large as 650 people. That kept me from being as close as I wanted to be to the front line. I am excited to be back in a role where I can maintain relationships with most of the folks on my team.

In terms of challenges, one that I try to keep in perspective is that our self-service rates and the percent of customers who are able to use the platform intuitively are very high, so the customers we speak to are only a small percentage of the total. This is also important to remember when it comes to advocating for product enhancements and deciding what updates might serve the greatest audience. Recognizing this helps me ensure that conversations we have with our Product and Engineering teams remain

What’s an accomplishment you’re most proud of?

One of the best life decisions I’ve ever made was moving to the Philippines sight unseen for a multi-year contract to lead contact centers for HSBC.

More recently, my department has seen a significant increase in internally promoted employees, which is a great reflection of my team’s career development efforts.

That’s fantastic. What are some important lessons you’ve learned about leadership? Are there any failures that you’re indebted to or advice you’d offer other women—including your own direct reports—who aspire into a position like yours?

I tend to keep my leadership philosophy simple: Be as transparent as possible and be vulnerable with your team. I work very hard to provide my team with a candid look into how we get work done. I think this context helps people understand why change may not happen as quickly as we would like, or happens more quickly than anticipated. I believe that, as leaders, we don’t want to overshare “how the sausage is made,” but any time we can provide additional insight and help our teams feel as though they are on the inside of the process, the more we build advocates.

I do my best to be the first one to admit when I’ve made a mistake. I think we’ve focused too much on being “strong” as leaders. Strong can be taken to mean infallible or “unchallengeable.” I encourage my team to tell me when I’m on the wrong track. The only way to create a safe space for them to do that is to point it out yourself.

In terms of advice I’d give others: Be yourself. Don’t let gender expectations define you. If you are highly maternal and caring, lean into it. If you are direct and decisive, lean into it. No matter what you are, lean into it. I spent a large part of my life thinking that feelings make you appear weak. Leveraging all of yourself and not compartmentalizing will make you the best leader you can be.

Be yourself. Don't let gender expectations define you. If you are highly maternal and caring, lean into it. If you are direct and decisive, lean into it. No matter what you are, lean into it.

What do you value in a workplace, and at Squarespace, in particular?

The reason I am working at Squarespace is because its company values align with my personal ones. Squarespace focuses on taking care of its employees and empowers all members of the organization to influence the product and business. For example, there is a monthly program called “Tell Us More” which allows anyone within the organization to directly impact our product roadmap by

We have incredible benefits and a caring team, and always take direct action on our annual engagement survey results.

Squarespace’s Portland support center has been featured for its non-call center-like design. It reminds me of the vision of a customer service center conjured by wellness expert Jenny Dempsey. What’s it like working in the space, and how does it speak to your own philosophies about what works best for a support team and for customers?

Squarespace’s office design enables employees to have control over their work environment. If you want to focus without distractions, you can work in our “quiet car.” If you’d like to work in a casual and communal space, grab a bean bag. If you’re on break and need to blow off steam, play video games in the vault.

Allowing employees the flexibility to choose their space is one small way we empower our staff. With a role as structured as those on the Customer Operations team, any opportunity we have to allow an employee to customize their work style should be taken advantage of. The more comfortable you are with your space, the more able you are to focus on your customer.

sqsp office
Photo by Squarespace

This customized service aligns perfectly with Squarespace’s support philosophy. Our goal is to offer individualized service to every customer and inquiry. We empower Advisors to use their own language to give customers recommendations, coupled with our amazing guides. We recognize that some customers need more than a guide to help them on their way, so each contact is evaluated based on that customer’s particular needs.

What are some tips for others managing support centers? What have you learned works best, and which aspects of the employee experience are you most concerned with?

My main tip is to manage and develop your staff as individuals. I think it is very tempting to generalize and programitize development. Though programs are helpful elements of development, the key is the relationship you have with each of your direct reports and throughout the organization. Understanding the needs of each individual on your team allows you to offer development opportunities, benefits, and coaching that best fits their needs. This tends to be much more work than creating a one-size-fits-all program, but it pays dividends.

Allowing employees the flexibility to choose their space is one small way we empower our staff.

One other area I am trying to focus on now is honoring the front line job. The work our Advisors do is key to the business and should be appreciated and celebrated. Many times, we focus on what people are doing outside of their main role. We honor a completed project or a successfully launched event. Though these are important, we shouldn’t downplay the importance of coming in every day and focusing on customer support. Continuing to discuss the

What about outside of work? Who are you and where do you spend your time?

The first answer that pops into my head is that I’m a mom outside of work. I have a highly energetic six-year-old daughter and two-year-old pup named Baxter. When I’m not in the office, I do my best to spend as much time as possible with them, and with my husband.

Favorite book: A Moveable Feast by Ernest Hemingway
Favorite app: Does Gmail count? I am a believer in inbox-zero.
Best ways to de-stress: Long walks and wine
Best way to build relationships with colleagues: Ask how you can help them

My peers and direct reports are full of examples of female leaders who I aspire to be more like. I admire that they are direct and open, participate in constructive conflict, and are caring, customer-focused, and engaging people.

Who are some women—alive, dead, fictional, real, in any realm—that you look up to, and why?

Maybe I’m too grounded in the day-to-day, but the women I look up to the most are those that I work with every day at Squarespace. My peers and direct reports are full of examples of female leaders who I aspire to be more like. I admire that they are direct and open, participate in constructive conflict, and are caring, customer-focused, and engaging people. These strong women continue to develop our future leaders to follow in their footsteps.

Millions turn to Squarespace for a great customer experience

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