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Margaret Smith ‘06 Kicks Off Women's Leadership Speaker Series

Jennifer Loprinzo


Thursday School Meetings are typically reserved for our “Saints on the Hill” program, wherein a member of our community addresses the entire school and shares a closely held piece of their personal story. On Thursday, December 9, our community welcomed a “Saint Beyond the Hill” back to campus—Margaret Smith ‘06—who spoke to students about her journey since the hilltop and the impact that her Canterbury experience has had on her success. Margaret’s invitation to campus launched the Women’s Leadership Speaker Series, hosted in honor of Canterbury’s ‘50 Years of Coeducation’ celebration, which is bringing distinguished members of our alumnae family to the school to share inspiration with our students. 

While a student at Canterbury, Margaret held nearly every leadership position, serving as a Sacristan, Lead Ambassador, two-year Dorm Proctor, and field hockey Captain. She hails from a long line of Canterbury graduates: grandfather Gerard Smith ‘31, father Hugh Smith ‘72,  sister Courtland Smith Stevens ‘01, brother Gerard “Chopper” Smith ‘04, and many uncles and cousins spanning a legacy of more than 90 years.

Margaret graduated from Hamilton College, NY, in 2010 with a B.A. in Government and a concentration in Psychology. She began her career in 2011 as an account executive at a New York City-based advertising agency, SS+K, specializing in creative social engagement. After three years there and knowing she wanted to have a greater impact on the end customer, Margaret moved on to a global executive search firm, Russell Reynolds Associates, where she worked with Fortune100 companies in the technology space. Margaret credits this experience with introducing her to the broader technology industry and, more importantly, the infectious passion of the leaders working within it.

In 2014, Margaret recognized a need in the executive search market to help early-stage tech companies build their boards and leadership teams with a more hands-on, consultative approach. This led to Margaret becoming one of the founding members of Rich Talent Group, a leading San Francisco-based executive search and advisory firm focused on consumer growth technology companies. During her four years at RTG, Margaret successfully built executive leadership teams at companies including Airbnb, Dropbox, Etsy, Eventbrite, Warby Parker, Uber, and Zillow. In addition, Margaret partnered with many Silicon Valley venture capital firms to advise their portfolios through periods of hyper-growth. “I found great reward working with company founders during crucial moments of scale by helping to solve their most pressing needs with the right people—aligning skill sets, cultural fit, moral compasses, and timing,” said Margaret. “The adrenaline of being a very, very small part of these companies’ success (and failures) was exhilarating. Ultimately, however, I was on the outside as a consultant and knew I wanted to experience more of this reward firsthand.”

Intrigued by the real estate industry (her parents are both real estate agents), Margaret joined Compass, Inc. in 2017 as Head of Talent at a time when the firm was still an early-stage startup looking to change the way people buy and sell homes through a proprietary technology platform. Appointed to her current role as Global Head of Talent in 2020, Margaret’s primary focus is the management of a team that has grown from five when the company began to 150 people today, who are spread across the United States and India and accountable for Compass’s year-over-year people growth. “My job is to empower the team to move fast, to assess accurately, and to ensure we are solving critical Compass business needs with the right people,” she described. 

During her four-year tenure with the company, Compass has grown revenue from $370 million to a projected $6.4 billion in 2021 and the employee base from 200 to more than 5.000. Likewise, the company has expanded from five major cities to now serving half of the U.S. population with 300+ offices nationwide. The company made its market debut on the New York Stock Exchange with an initial public offering in April 2021.

Margaret described her career path to students as a mix of hard work, good timing, and most importantly, solid foundational principles that were introduced and developed during her formative years at Canterbury. “I vividly remember my morality class with Mr. Simonelli in the downstairs chapel classroom where we studied the concept of servant leadership,” Margaret said. “The leader in any circumstance—work or life— existing to serve their people. Leading with empathy, humility, stewardship, and community, ultimately putting others' needs before your own. I saw this lived out by all my teachers and coaches every day during my time here, along with their strong encouragement of me to build leadership muscle through roles like Sacristan, Proctor, and team captain.”  

“I credit servant leadership for my success and ease in leadership roles to date,” Margaret continued. “I have certainly learned a lot through my career so far … and I am hugely grateful for this foundational grounding and the sincere reward I get from helping individuals realize their potential.”

Margaret also attributed the strong sense of self-reliance instilled at Canterbury as another guiding rudder throughout her career. “It was not obvious to me at the time, but being treated like an adult as a student at Canterbury taught me to be responsible for my own decisions, all within the safety and comfort of an incredibly supportive community that was there to catch me.”  She continued, “I think back to living without my parents during those formative years, experiencing the extreme vulnerabilities of high school and consistently being encouraged to chart my own path, rely on my instincts, and embrace my individuality. I am grateful for the delicate balance of supportive teachers and coaches, who gave me just enough room to fail effectively.”

Lastly, Margaret praised Canterbury as being instrumental in helping her understand the importance of compassion. “My appreciation for genuine compassion was developed through a number of pivotal service events during my time here as well as the expectation that, as a member of this community, you are always looking out for each other and helping one another succeed.” Margaret went on: “There are no filters in a close-knit community and especially in dorm life, where you see everyone’s whole self—their ups and downs, insecurities and strengths. This was a powerful experience for me, resulting in a sense of belonging, confidence, and ultimately compassion that has guided the way I hold myself as a professional, as a friend, and as a community member.”

Bringing her School Meeting address to a close, Margaret left students with some brief advice: “What makes someone successful in life is not one-dimensional; it is not a grade or an athletic performance. Focusing on your guiding principles, your motivations, your emotional intelligence, and how you treat others is important. Having the privilege to work with a great deal of our tech industry's top leaders, they are driven by passion, a strong sense of self, and a purpose to make the world a better place. They are not superheroes; they are people just like you.”

Margaret’s visit to campus continued following School Meeting. She joined Sixth Form students enrolled in our SUPA Entrepreneurship and Global Economy class and continued the discussion about qualities she looks for in leadership candidates. She then chatted with members of the Women of Canterbury affinity group over lunch and shared more stories of her career as a female executive.    

We are immensely grateful for the time Margaret spent with students and faculty on campus and cannot wait to welcome her again soon. 

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