4월 중순, 뉴욕 소호(Soho)에 위치한 이커머스 테크 스타트업인 Rokt 사무실에서 패트릭 커노튼(Patrick Connorton) 변호사는 따뜻한 포옹으로 나를 맞이했다. 로펌 시절 동료였던 그가 기업 가치 20억 달러, 가장 빠른 성장세를 보이는 기업 리스트에 오른 'Rokt'의 법무 총괄이 되기까지 다이내믹한 커리어를 살펴본다.
패트릭은 어릴 적 꿈이 작가, 스피치 라이터나 기자였다. "글 쓰는 걸 좋아했어요. 만일 변호사가 된다면 다른 일에 실패해서 일거라고 늘 얘기했죠."(웃음) 대학 졸업 후 로펌에서 패러리걸로 일한지 몇 개월 안 돼서 2004년 대통령 선거 민주당 후보자인 존 케리 캠페인에 취업을 한다. 케리 당선 실패 후, 선거 캠프에서 다양한 일을 하는 법조인들을 만난 계기로 포덤 대학 로스쿨에 입학하고 모두 갈망하는 대형 로펌 오퍼뿐만 아니라 뉴욕 연방법원 클럭십과 2nd Circuit 항소법원 클럭십까지 따낸다. “연방법원 인턴일 때 의견 초고를 작성했는데 클럭이 고칠 것이 없다며 판사님께 바로 제출했어요. 그 뒤 클럭이 되어 달라는 판사님의 제안을 받았죠." 탄탄대로일 것만 같은 커리어의 시작이었다.
기업가치 20억 달러 Rokt 법무총괄 패트릭
다양한 실패 덕분에 변호사에서 창업가·리더로 변신
자신의 길 개척하는 담대함 우리 모두 가질 수 있길…
클럭십 후 뉴욕 심슨 대쳐 로펌에 어소시에트로 일을 시작하지만 곧 흔들리기 시작한다. 2008년 금융 위기로 인한 서브 프라임 모기지 사건만 반복해서 맡았고, 고된 업무와 스트레스뿐만 아니라 모든 이슈에 적대적인 입장을 취해 싸워야 하는 송무에 회의를 느낀다. 뉴욕 검사 포지션에 낙방한 후 다른 로펌으로 이직을 하면서 더 다양한 사건을 맡았지만, 자신이 원하는 삶이 아니라는 생각이 굳어졌다. 어느 날, 커리어 고민을 털어놓았던 친구로부터 "같이 사업할래?" 라는 질문 한 줄과 100페이지에 달하는 사업 계획서가 이메일로 온다. 플라스틱 병 쓰레기를 줄이는 친환경 미션을 가진 소셜 벤처 기업인 '리필(Reefill)'의 탄생이었다. 뉴욕시의 커피숍과 베이커리의 네트워크를 애플리케이션으로 연결하여 필터된 생수를 제공받고 구독료를 내는 이 서비스는 액셀러레이터에 합격하고 피치 대회에서 우승하여 지원금을 받는다. 그렇게 패트릭은 공동창업자로 또 다른 삶을 시작한다.
창업 초반에 언론에서 많은 관심을 받게 되고, 물 필터 업계 세계 1위인 독일 회사 브리타(Brita) 대표와의 미팅 후 인수 계획까지 이어진다. "신나는 날들이었어요. 인수 계약 조건 서류를 협상하고 구두 계약까지 갔죠." 하지만 결국 딜은 무산되고 만다. 다시 7억 원 투자를 유치해서 사업을 이어갔지만 상황은 녹록지 않았다. 서비스가 설치된 커피숍에서 하루 종일 소비자의 반응과 문제점을 관찰했다는 그에게 사업 체질이었냐고 물으니, 고개를 절레절레 흔든다. "사람들에게 무언가를 해 달라고 설득하는 건 어려운 일이에요. 하지만 타고난 성향이 아니어도 내 일이 되면 할 수 있단 걸 알았죠."
패트릭은 리필에서 발생하는 법적인 이슈를 도맡았고, COO를 겸했다. 송무 변호사가 어떻게 그런 일을 했냐는 질문에 웃는다. "무조건 공부했죠. 필요할 때 외부 자문을 구하더라도 한번은 내 손으로 시도하는 원칙이 있었어요." 창업은 천국과 지옥을 오고가는 경험의 연속이었다. 브리타에 인수될 뻔했을 때, 리얼리티 쇼인 샤크 탱크 오디션에 합격해서 나갈 뻔했을 때는 날아가는 기분이었다. 반대의 경험은 더 많았다. "부정적인 시각으로 보는 반응도 있었어요. '비열한 테크 브로(tech bros)'라는 말도 듣고…." 그는 영국 가디언지의 기사를 언급한다. 기업이 이윤추구를 위해 공공재를 사유화하여 민주주의를 훼손시킨다고 비판하는 기사의 서문에 그런 기업의 예로 리필이 등장한다. "정말 마음이 아팠어요. 선거 캠페인과 변호사 업무를 하던 내 소신, 환경 오염을 줄여보자는 진심, 내게 중요한 가치와 반대로 평가하니까. 아내에게 얘기하며 울 뻔했어요." 그는 결국 사업을 접게 된다. "모든 방법을 시도했지만, 매출은 안 나오고, 돈도 못 벌고, 집엔 갓 태어난 아기가 있었어요. 팀과 고심 끝에 그만하기로 하고 투자자들에게 투자금을 돌려 줬죠. 너무 놀라더라구요. 사업 접은 것 보다도 투자금을 돌려준 팀은 처음이라고."(웃음)
리필이 정리된 후, 테크 기업 취직을 목표로 인맥을 총동원해서 구직 시장에 뛰어들었고 창업 경험을 높게 산 Rokt에 입사를 한다. 2명인 법무팀에 들어가 곧 팀원의 퇴사로 급빠르게 성장하는 스타트업의 모든 법무를 책임지게 된다. "평생 이렇게 열심히 일해 본 적이 있나 싶을 정도로 많은 일을 했죠. 개인정보 정책, 계약서 협상, 투자 유치 관련 업무, 주주 총회 - 모르는 것투성이였기 때문에 전문가가 될 때까지 팠죠." 창업가로서의 경험이 도움이 될까. "100% 도움 돼요. 하루를 살아내는 것이 얼마나 힘든지 아니까 시각이 달라진 건 분명하죠." 법무의 역할에 대한 시각이 바로 그것이다. 그는 주요 결정의 옵션을 논의할 때 안전한 쪽에 초점을 두지 않는다. "리스크가 두려워 중요한 딜을 말리기 보단, 위험을 감수하더라도 되게 만들어야죠. 특히 이 분야는 개인정보 보호와 보안이 중요하기 때문에 법무가 능력이 있고 믿음을 줄 수 있어야 파트너와의 딜이 성사돼요.” 급속도로 성장한 Rokt 는총 직원 450명에 세계 6개 나라에 지사가 있다. 티켓마스터, 부킹즈 등 인상적인 파트너와 클라이언트 명단이 있고 언론에서 IPO 계획에 대한 뉴스도 들려온다. 패트릭의 리더십 아래 법무팀은 8명으로 늘었다. “리더는 two way street을 만들어야 해요. 개개인의 이야기를 듣고 질문하고 모두 성장할 수 있도록 대화를 끌어내야 하죠.” 시리즈 C 부터 최근 4200억 원 투자금을 유치한 시리즈 E 과정에서 핵심 역할을 한 그에게 일을 대하는 기준이 있는지 물어봤다. "생존이죠. 다른 이유로 실패를 하더라도 노력이 부족해서 실패하지 말자." 이제 진정한 테크 브로가 되었으니 뭘 하고 싶냐는 농담에 웃는다. “이 회사가 성공할 수 있도록 뭐든 합니다.”
변호사가 된다면 무언가에 실패해서일 거라던 그는 다양한 실패 덕분에 변호사뿐만 아니라 창업가, 전략가, 그리고 리더가 되었다. 다른 미팅으로 뛰어가는 그를 보며 얼마나 쉽게 좁은 시야로 실패나 성공으로 오늘을 평가하는지 생각했다. 패트릭의 스토리는 현재의 고군분투가 꼭 필요하다는 믿음, 절실한 노력으로 커리어에서 의미를 찾고 인정받을 수 있다는 희망을 준다. 눈 부신 태양은 어두운 밤을 지난 후에야 만난다. 실패로 얻은 날개로 자신의 길을 개척하는 담대함을 우리 모두 가질 수 있기를 바라본다.
이소은 외국변호사(미국)/가수
[인터뷰 영어 원문]
I enter the offices of Rokt on a relatively quiet street in the bustling SoHo neighborhood. The receptionist welcomes me with a friendly Aussie accent as I wait for Patrick Connorton, a former colleague and the current General Counsel of Rokt, an e-commerce tech startup that has been named by Inc. magazine as one of the fastest growing companies in America. He greets me with a hug and a calmer demeanor than I remember from our law firm days. We grab a drink from the well-stocked kitchen and settle into a booth.
Patrick was born and raised in New York. His father was a lawyer who was very involved with New York Democratic politics. I ask if that environment propelled him to this profession, but he immediately corrects me saying he wanted to be a writer, journalist, or a musician. “I always said that if I went to law school, it would be because I failed at something else." After graduating from college, Patrick worked as a paralegal at a law firm in Washington, D.C. Not long after, he got a job working on John Kerry’s 2004 presidential campaign. “I spent months living in a supporter’s house in Omaha, trying to get local press to cover the campaign.” After the election, he returned to New York and started to consider law more seriously, ultimately attending Fordham University School of Law. He secured two highly coveted federal clerkships ― one at the Southern District of New York and another at the Court of Appeals for the Second Circuit, as well as an offer from a prestigious white shoe law firm. It seemed to be the start of a promising career.
After his clerkships, Patrick started working as an associate attorney at Simpson Thacher & Barlett. The 2008 financial crisis led to an explosion of mortgage-backed securities cases, on which he was staffed repeatedly. The long hours, stress, and uncertainty about the type of work he was doing made him question his career choices. “With every case, I had to take the maximalist extreme position and bring up all this false indignation, just because we were litigators and had to be that way. It was exhausting.” He began searching for a different path and applied to become a prosecutor but ultimately did not get the job. He moved to another law firm and took on a wider variety of cases, only to realize that was not the life he wanted.
He confided in a friend about his career misgivings. The next day, he received an email with a one liner: “Want to start a business?" A hundred page business plan followed. It was the birth of the social enterprise “Reefill” and Patrick’s new chapter as a co-founder. Reefill was a social venture with an eco-friendly mission to reduce plastic bottle waste. The service provided a network of water refill stations connecting coffee shops and bakeries in New York City with an application that gave access to filtered water for a subscription fee. In the beginning, Reefill received much media attention, even catching the interest of the CEO of Brita, the German water filter company, who flew to New York to meet the Reefill team and discuss an acquisition. "It was really exciting. We negotiated and put together a term sheet and had a handshake deal." Unfortunately the deal fell through. Reefill’s team trudged ahead, attracting modest investments from angel investors whom he met by “networking like crazy”. I ask him whether he had always been entrepreneurial or had a business-savvy “hustler” mentality. Right away he shakes his head. "It's very difficult to convince people to do something. But I learned that if it is my job, I can do it even if it's not my natural inclination." He talks matter-of-factly about how he spent entire days sitting in coffee shops where the service was available, watching consumer reactions and noticing problems that needed fixing. “I learned that consumer experience had to be seamless, that people actually don’t read the information that companies provide, which is why the business model has to be so intuitive.” Patrick assumed the Chief Legal Officer and Chief Operating Officer of Reefill, which he jokes was a three person team. I ask him how a litigator provided those functions, which call for an entirely different skill set. "I studied like crazy ― researched and tried to master everything. We had outside counsel when we absolutely needed it, but I always took a first pass at any issue.”
Patrick has a wealth of stories about his entrepreneurship days at Reefill that sound like the premise of a mockumentary series. He tells me details about the failed acquisition by Brita and about the time they were invited to go on Shark Tank. The most engaging stories however, are not the highlights, but the lows. "There was a negative reaction, which was so unexpected. I remember people calling us these tech bros that were trying to make money off of water, which is a human right.” He looks at me incredulously. “Me, a tech bro?” He mentions an article in the Guardian that criticized Uber and other companies for privatizing public utilities for the sake of profit, going so far as to say that they were undermining democracy. Reefill was the subject of the opening two paragraphs in the article. “It was heartbreaking. Everything that I had done on the Kerry campaign, my work as a lawyer, my sincere belief in the environmental impact of our company ― it felt like I was being punched in the gut. I almost cried telling my wife that story.” He says that starting a business is being able to take a gut punch everyday and still move forward, which he tried to do. Ultimately, the challenges became too much to overcome. “We tried everything under the sun, but it just didn’t work. We couldn’t make a profit. We all had families, I had a newborn at home. I remember telling my co-founders that someone had to tell me to take my hands off the wheel.” After the difficult decision to shut down, they returned the funding they’d received to their investors. He laughs, “They were so surprised that we returned the money, more than the fact that we decided to close the company."
After the tumultuous ride at Reefill, Patrick was sure of only one thing: he did not want to return to private practice. He mobilized all of his personal and professional connections with the goal of working at a tech company and ended up joining Rokt as Senior Corporate Counsel in a two-person legal team, where the CEO appreciated his entrepreneurship experience. Soon after, however, his boss left the company, and Patrick once again found himself responsible for all legal affairs inside a rapidly growing startup. "I worked harder than I’d ever worked in my life. Data privacy, contract negotiation and drafting, labor issues, investment related work, shareholdermeetings ― I forced myself to become an expert.” I ask whether his experience with Reefill helps in his current job. "It's 100% helpful. I know how hard it is to start a company, to take a risk, and to generate revenue. It’s not easy but I do have some perspective.” Patrick has a keen understanding of what it is like to be a founder, and that perspective characterizes how he views the role of legal at the company. When discussing options for a major decision, he doesn't focus on being less risky. "I want to be the guy that makes the deal happen, rather than the person that says ‘no’ because it’s risky. Especially in this industry, data privacy and security are extremely important, so having a legal department that is competent can help the deal happen.”
Rokt has grown rapidly in the past several years. It currently has offices in 6 countries with over 450 employees and an impressive list of clients and partners such as Ticketmaster, Live Nation, Bookings, etc. The most recent Series E funding round secured $325 million in investment and the company has solidified its unicorn status with a valuation of $2 billion. Various media channels have reported whispers of a potential IPO. The legal team under Patrick's leadership has also grown to eight members. “It is really important as leaders and managers to always create a two-way street, to meet individual team members where they are, to listen and ask questions so everyone can grow.” What is his mantra in approaching his work? He pauses before replying, “Survival. Making it through the day. I might fail at this for other reasons, but not because I'm not working hard.” I ask him jokingly what he wants to do now that he’s a real “tech bro.” He laughs, but responds thoughtfully, “Everything I can to make this company successful.”
As I watch Patrick run to another meeting, I am reminded of what he said earlier in our conversation ― that if he had become a lawyer, it would have been because he’d failed at something else. Patrick had become a lawyer, an entrepreneur, strategist, manager, and a leader because of those so-called failures. I ponder over that all-too-common word, failure ― and what it means in our everyday lives as we forge ahead, turn unexpected corners, and sometimes take a leap of faith. I think of how we judge our lives within the narrow lens of the present, without the wisdom of foresight or the forgiveness of hindsight. Perhaps that is why we need stories like Patrick’s, to remind us that challenging roads can lead us to where we need to be, that with hard work, persistence, and the support of people we love, we will find our role in the world and add value through our work. That we can and will, make it through the day.