Sometimes, when two colleagues are mutually committed to goal setting and continuous reflection, a mentorship can begin out of nowhere. Roberta Meo and Rachel Carey of Squarespace are proof that this kind of organic relationship building can result in some of the strongest bonds.
“Squarespace’s culture cultivates the conditions for mentorship,” says Meo, who is Vice President of the company’s Channels and Services department. After all, her mentorship with Carey, a Project Manager in Customer Operations, began with the two catching up over coffee and increased in frequency and depth over time.
“We may talk about what I’m working on or we may talk about what’s happening outside of work in addition to my career development,” Carey adds, noting the difference between her focused one-on-ones with her manager and her less formal conversations with Meo.
The women recently shared with us how their mentorship has enriched their career paths at Squarespace and also spoke about the company culture that made this dynamic possible. Check out what they had to say below.
Tell us a bit about your job. What’s your current role, and what did your career path look like prior to being in this role?
Roberta Meo: I’m the VP of Squarespace’s Channels and Services department, which is a talented team that focuses on developing and scaling new customer segments outside of our target customer. Our focus is to manage and engage our professional user community, Circle, scaling our Marketplace, and incubating new services and solutions. Prior to this, I built my career mainly in operations and business development, leading teams of scale.
Rachel Carey: I’m a Project Manager dedicated to the Customer Operations department at Squarespace, the all-in-one website building platform. I execute large-scale, cross-departmental projects that are impactful to the business. Recently, I led the migration of Squarespace’s Community and Circle forums and supervised the strategy, design and technical needs of the project. You can find the new forum here.
Prior to my role as a Project Manager, I was an advisor at Squarespace. As an advisor, I provided technical support to Squarespace’s customers, aided in the onboarding of new hires, provided individualized help in one on one workshops at Industry City and Impact Bazaar, and created the Exchange Program.
What’s your favorite thing about your job? And what about your company?
Roberta Meo: The best part of my role is that I get to collaborate across the entire organization on new initiatives that will shape the future of the company. Being exposed to all departments, and the fascinating people that they’re made up of, allows me to learn something new every day and allows me to feel connected to the company as a whole.
Rachel Carey: I wake up each morning excited to go into Squarespace where I get to work with some of the most creative and intelligent colleagues I’ve ever worked with, while supporting a product I believe in. In my role, I love being given a problem, coming up with multiple solutions and then executing. I enjoy how challenging my role can be and the ability to work with my colleagues cross-departmentally.
How long have you served as a mentor/sponsor, and how did you wind up becoming one?
Roberta Meo: Early on in my career, I met someone who I cherish as an informal, yet essential mentor. I knew soon afterwards, that I would love to serve someone else in the same position if I could. Since then, I’ve been fortunate enough to manage many wonderful people, several of whom sought varying degrees of mentorship, so it happened naturally. Now, more often than not, the relationship starts with a conversation over a cup of coffee. Mentoring has become such a gratifying part of my career, and I love coffee, so it’s a win-win situation.
This is how Rachel and I started meeting every few months; it began with us catching up over small talk, and it evolved from there. Rachel is driven and thoughtful when it comes to her career, which makes a great launching-off point for a mentorship.
Rachel Carey: Roberta and I have been meeting informally every few months since she returned to Squarespace to lead Channels & Services, a newly established department. Roberta has always been someone I’ve looked up to and respected. While leading the Customer Operations department, she was able to strike the difficult balance between effectively managing a support team and ensuring the customers’ support needs were met.
Does your company have a formal program in place for mentor/sponsorship, or is it more of a casual thing that happens organically?
Roberta Meo: While no formal program is currently in place, Squarespace’s culture cultivates the conditions for mentorship. With a leadership team that encourages new ideas and initiatives, combined with a brilliant and creative workforce, the conditions are ripe for social mentorship or, even, just some personal guidance. From my experience, the combination of factors above are hard to find, and what makes Squarespace an incredible place to build your career.
How do you approach your role as a mentor/sponsor differently from how you approach your own work (and perhaps your role as a manager if you have direct reports)?
Roberta Meo: Certainly the pressure comes off on in the mentor/mentee relationship versus a traditional manager one, as performance updates are naturally going to be less rigid. The advantage of this is that both the mentor and the mentee can be more vulnerable. It’s important that the mentor holds the mentee accountable for their goals. A mentorship often involves friendship, but it should come with the expectation that the mentee is committed to furthering their goals.
As an example, Rachel and I have built up a relationship overtime that has extended from work and career talk, to things going on in our personal lives. It’s been a natural progression and a really nice one. We both learn things from each other.
Rachel Carey: With my manager, my one on ones are very focused. The agenda is typically the same from week to week. I update him on the status of each project I’m working on, surface any blockers and escalate as needed, as well as how I’m tracking toward my career goals. With Roberta, it’s much more informal. We may talk about what I’m working on or we may talk about what’s happening outside of work in addition to my career development.
Earlier in your career, did you have a menor/sponsor yourself? If so, what did you learn from them? If not, why do you wish you’d had one?
Roberta Meo: I attribute the main reason I’ve had a career in operations and leadership roles to key sponsors who’ve coached me early on in my career. They supported me and helped surface opportunities to stretch my skills, and encouraged me to take roles that I didn’t think I was ready for at a very early stage in my career. They taught me to put myself forward when an opportunity presented itself, and to keep pushing myself to learn and develop. Many years later, I’m still learning and developing, and hope that will always continue.
By being a leader in your career, what are some ways that you’ve enriched the lives of those around you in the workplace?
Roberta Meo: A lot of us spend the bulk of our time in the workplace and one of the things I try to bring to my colleagues is perspective and enjoying the time we have with each other. It's important that we all strive for success but, over the medium and long term, we will not be able to reach our goals if everyone is too stressed to extend their wings. This means celebrating wins together and being comfortable with failure. This should help maintain everyone's confidence, and an assured team is a happier and more productive team.
The human experience seems to be really important to you. What are some ways that you champion this every day?
Roberta Meo: I spend time getting to know the people on my team, not only because it helps build trust but because I’m genuinely interested in learning more about them and their interests outside of work. It helps me to be empathetic to situations they are going through personally and supportive where I can be from a work perspective. We all have our personal struggles and having worked with different types of people, I know it is always a relief when someone you work with takes an interest in you as a human. It’s a lesson I have tried to pay forward to my colleagues.
What’s the no. 1 thing you think women should know about working at your company?
Roberta Meo: Squarespace is truly an amazing place to be a working mother. The tangible benefits for working parents are top notch, but the company goes much further than that — there is no stigma for having to take the time necessary that all working parents need. This includes things such as emergency trips to the pediatrician, childcare mix ups or wanting to see your kid’s soccer games. I believe working mothers at Squarespace universally appreciate the company’s empathy and reciprocate their gratitude by coming into work every day to produce great work.
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