Mary Good, Chief People Officer for leading all-in-one website building and e-commerce platform company Squarespace, recalls a recent moment when she was reminded of the power of the company’s culture. In early 2020, Good had set up an email inbox so any employee knew where to go with questions about the then-burgeoning COVID pandemic crisis. Good wanted to find ways to make herself available to employees and decided early on that she would respond to as many messages from employees herself as she could, citing her own feelings of wanting to personally connect with employees despite everyone working remotely.
“What kept astounding me is how many times those employees would say, ‘Hey, Mary, thank you so much,’” she says. “They would ask ‘How are you doing? What can we do to help you? They would write, ‘I’m here if you need a volunteer, I just wanted to say thank you to the whole team. Thank you to our leaders for everything you’re doing.’ And to me, that amount of graciousness, gratefulness, and selflessness Is something that I think really is unique and distinctive about this culture.”
Good notes that she loves meeting Squarespace customers in her daily life, adding that it’s heartening how many of these customers are enthusiastic ambassadors of Squarespace’s brand.
“It happens all the time,” she shares. “When I first started at the company, in my first week of living in New York City I couldn’t believe how many people I was running into in my everyday life who were Squarespace customers and huge fans of our company. That included the person who cuts my hair, a professional artist I met in my local coffee shop, and the leader of a rock band playing a party I attended.”
ROAD TO SQUARESPACE
Good had been the head of HR at six companies – four private, three public – prior to joining Squarespace, where she is thoroughly enjoying her time and hopes to make a lasting impact.
“I’ve done a lot of different things,” she says. “The thing that all of those experiences have in common is that they’ve been high growth technology companies with founder-driven cultures, which I think is something pretty unique. It’s something that I’ve gravitated towards and is also a big part of the reason that I joined Squarespace.”
The importance of Squarespace’s mission is what drew her to the company, Good says, as well as the appeal of working amidst the many engineers, designers, and creatives who make up much of the company’s workforce. She also was deeply impressed with company Founder/CEO Anthony Casalena.
“When I met Anthony, that was a huge selling point,” Good says. “Despite being a founder who has pivoted many times over the course of the company’s 18-year history, I just loved how grounded he was in the kinds of people he wanted to work with. And he has stayed true to that since day one.”
“When you have a founder who has been there since the beginning, and who has really inspired the company’s purpose, he or she is always going to be looking at things from that lens,” she continues, describing her fondness for founder-driven companies in general and Casalena specifically. “A founder-led company enables you to have a clarity of vision and focus on prioritization that I think that in other companies can become a bit diffused.”
TEAM SUCCESS
Good describes the kinds of people who make up Squarespace as highly competent, always curious, and low-ego. At Squarespace, she says, “it’s all about team success rather than focusing on individual success. You don’t find that level of collaborativeness and really cheering one another on at every company and it’s something that I believe makes Squarespace really special.”
The company’s C-suite diversity was also a major draw for Good: “This is one of the few times I’ve worked in a company as part of the C suite where I was not the only woman. Our C-suite is more than 50% women and being around other women leaders provides a real sense of community. It’s tremendously inspiring and motivating.”
As far as personal guiding lights, Good says she’s built them from the ground up starting at a very young age. Her parents, she says, instilled in her the absolute importance of caring for other people as whole human beings and the notion of servant leadership.
“To me, these principles are so foundational, in terms of the companies that I want to be part of, and the cultures that I want to try to help to thrive,” she says. “I start there, with the fundamental belief that human beings are the differentiator of success for a company. To me, that’s absolutely core.”
A DEEPER MISSION
People leaders, and people teams in general, are all about making sure the soul of the company stays intact, Good says. That deeper mission informs everything, whether it’s how the company develops leaders or, more recently, the company’s COVID response.
“In typical Squarespace fashion, we comprised a cross-functional COVID task force made up of members across the business,” Good says of the company’s immediate pandemic response. “Our head of engineering, our general counsel, and a number of other key leaders joined me as part of the task force, and we quickly started to try to understand and put our arms around what was going on.”
As the crisis escalated, Squarespace ended up shutting down offices and shifting to remote work.
“Over the course of the last year-plus, what we’ve really tried to do is to listen to our employees, and to be as supportive as we could be, given all of the challenges that we faced over the course of that year,” she says.
The early days of the pandemic were about adjusting to remote work for many employees who had never before experienced working consistently working remotely themselves, let alone as part of an entirely virtual workforce. The company provided employees with focused training sessions on how to work effectively and pace themselves given that people were working in the same place they were living. Squarespace also supported helping folks balance work with being caregivers.
“As time went on, and we learned more, we really focused on mental health,” Good says. “That was a massive priority for us. Because people were really just finding this situation to be enormously challenging on a whole host of dimensions, including working through the grief associated with losing loved ones.”
With Good’s impassioned help, the company has expanded its mental health offerings by adding app-based wellness programming including, Headspace, Talkspace, Ginger, and HealthJoy, by improving the networks of available therapists, and by consistently promoting their mental health and wellness offerings (through internal communications, seminars/webinars, and employee experience initiatives, to name a few).
In line with the company’s focus on the whole person, Good mentions they focused on additional elements that contribute to mental health and wellness for members of Squarespace’s employee population.
“We’ve expanded our parental leave program to be expansively-defined caregiver leave with a very broad definition” she adds. “We have also introduced among the most robust transgender Employee Benefit Program offerings available under any carrier [where we have offices] both in the United States and Ireland.”
Good is proud of how far Squarespace’s benefits offerings have come: “I think we have a really inclusive benefits program that is geared towards well-being,” she says.
Her own values of embracing the whole person, when it comes to every individual, connect Good naturally to Squarespace’s ethos of respecting creativity and individuality. She also firmly believes that nurturing a sense of belonging is a critical part of the company’s culture, and is not only committed to Squarespace’s focus on furthering diversity and inclusion but also to personally driving momentum behind the company’s progress in the DE&I space.
CHALLENGES
When it comes to workplace challenges that are currently top of mind for Good and the company, she notes the particular care that is being given to the return to office approach, particularly since there is not a one-size-fits-all approach that will work given the complexity of their global workforce.
“As a company, we want to be thoughtful and do things right, so – as much as possible – we can minimize having to redo them later,” she says. “We had a lot of flexibility before COVID started. And we’re anticipating that we will continue to have even more flexibility going forward. We have surveyed our employees and worked with all our department leaders and HR Business Partners to understand which roles can be more flexible or remote in order to inform our go-forward approach to return to office.”
Squarespace is equally considering the feedback from those employees who have found working remotely during COVID to be isolating and disengaging.
“We want to build out our employee networks, and really make sure we have offices that are conducive to collaboration, but that also give people quiet space,” Good says.
Good says any company growing like Squarespace is always in the midst of an act of transformation – if not outright reinvention. As she reflects on the past year and a half, and how Squarespace’s employees managed through it, resilience is the first word that comes to her mind, and something she plans to continue to focus on.
“Creating and cultivating an environment where people can be themselves and bring their whole selves to work is so important. Helping provide the tools and a supportive environment to enhance resiliency continues to be key. Setting up the ecosystem where people can embrace change, seeing change as the next level of challenge, professional development, and creative pursuit, is important,” she says. “As the Chief People Officer, and as part of the people team, there’s a big part of our job that is about shepherding people through change, no question about it.”
LIFE-LONG LEARNERS
For new hires, then, adaptability and flexibility are desired as well as promised. Squarespace thrives on “folks who are curious, and who are willing to put their ideas out there. Because creativity is so important to us.”
“When I was interviewing at Squarespace, I thought, ‘hmm I had better try building a website.’ I was taking the train from Boston to New York City, and within an hour and a half, I built myself a website on our platform and it looked fantastic,” she says.
No matter what it is – a website or something else – people at Squarespace truly enjoy building and learning. “The people who are life-long learners and enjoy being part of building something – those are people we would love to talk to.”
When asked for a final bit of advice for those starting out in their careers, Good offered us two.
● “Pick a company that is growing. Because with growth comes opportunity.’
● “Really examine, as closely as you can, the quality of that company in terms of the core values and the culture, especially for people leaders. Does the company walk the talk?”