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Management Team
Experience You Can Trust
Mae O'Malley
Founder/Managing Attorney
Mae O'Malley

In many ways, the personality of Paragon Legal reflects that of its founder. And Mae O'Malley lets nothing stand in the way of getting the job done, whether it's managing a rapidly expanding business, handling urgent client requests, or racing her three young sons down black diamond ski runs in Tahoe. She is a devoted mother who loves spending QT with her boys, and her determination to successfully balance all of life's important aspects is what inspired her to establish Paragon Legal in 2006. The objective: build a firm that could give senior attorneys greater professional flexibility and control, combined with opportunities to work on meaningful, challenging legal projects.

While friends say her gift for culinary creativity led them to envision Mae at the helm of a catering business, epicurean exploits will have to wait. Because with sterling credentials and more than a decade of legal experience specializing in IP and technology transactions—not to mention a team of 80+ seasoned attorneys—she also has all the ingredients to turn an innovative legal model into a winning recipe. Mae began her career at the top San Francisco firm Morrison & Foerster before working in-house at several growing technology companies. She served as corporate counsel for Evolve Software and Escalate, Inc., then joined Sygate Technologies as director of legal affairs. She led the legal side of Sygate's acquisition by Symantec Corporation in 2005, and then worked as senior corporate counsel for Symantec until early 2006. Following Symantec, she joined Google as a contract attorney, working on complex content licensing including the StreetViews deal, while simultaneously founding Paragon Legal. Mae received her J.D. from U.C. Berkeley's Boalt School of Law and her A.B. with honors in Political Science from Stanford University. She was named a Legal Rebel by the American Bar Association Journal in 2009.

Trista Engel
Managing Director
Trista Engel

After years of experience in corporate consulting, communications and finance, Trista Engel decided to take on yet another new and interesting challenge at the helm of Paragon Legal, where she says a positive, supportive culture is key to the company’s longtime success. As Paragon’s Managing Director, Trista’s focus on client development, attorney recruitment, and strategic growth initiatives fits perfectly with her love of problem solving, building great teams, and helping people achieve success in their careers.

Trista’s path to Paragon began more than a decade ago at Credit Suisse, where she worked as a fixed income analyst. She always craved a broad and growing business skillset so after several years she moved on to client management and strategic communications at the public relations firm, the Dilenschneider Group, and then to management consulting at Bain & Company.

Through her years in strategy consulting, Trista enjoyed becoming a part of each business and affecting its change for the better. She loved learning about new businesses and industries, helping problem-solve their most pressing strategic challenges, and making a difference in the organization, but she also felt a draw to commit to one business where she could see the strategy through and understand its long-term impact. This inspired her to co-found the entrepreneurial investment firm, Calyx Capital Partners, with Paragon’s Jessica Markowitz, with the goal of acquiring a single company that they could grow and nurture indefinitely. Together, Jessica and Trista successfully managed due diligence, equity fundraising and loan financing at Calyx, culminating in the acquisition of Paragon Legal in 2018.

Trista earned her M.B.A. with a 2-year Merit Scholarship at The University of Chicago Booth School of Business and her B.A. in Economics and History at Yale University. Trista was a 4-year collegiate athlete for the Yale Varsity Women’s Soccer Team, which captured the Ivy League championship and made the Sweet Sixteen of the NCAA tournament.

Soccer has been a constant throughout Trista’s life, whether she’s volunteer coaching or competing in local adult leagues. In her free time, she also enjoys spending time with her young son and husband, exploring the outdoors, hiking, wine tasting, and skiing.

Jessica Markowitz
Managing Director
Jessica Markowitz

Andrew Carnegie once said, “There is little success where there is little laughter”, and Paragon’s Managing Director Jessica Markowitz definitely embraces this philosophy.

Jessica has survived and thrived as a leader by injecting humor into difficult work situations. Over the years she’s honed her comedic skills performing Stand Up and Improv in New York and Chicago in her free time. But Jessica has had some serious successes too, including earning Turnaround Management Association’s National Large Turnaround of the Year Award in 2014.

At Paragon, Jessica is focused on operations, finance and accounting, human resources, process improvement, and strategic growth initiatives. A passionate leader who finds satisfaction connecting with people and collaborating to build successful solutions, Jessica values Paragon’s culture of integrity, as well as its commitment to helping legal professionals maintain challenging legal work in a different way.

Jessica received a B.S. in Management from Tulane University, before beginning her career as an Analyst at Lehman Brothers and The Royal Bank of Scotland. Jessica earned her M.B.A. from The University of Chicago Booth School of Business, concentrating in Finance, Accounting and Entrepreneurship.

After graduation, Jessica focused on turnaround and restructuring consulting, working directly with C-level executives from distressed companies while at Alvarez and Marsal, and later, The Keystone Group. She left Keystone to co-found the entrepreneurial investment firm Calyx Capital Partners with Paragon’s Trista Engel. Together, they successfully managed due diligence, equity fundraising and loan financing, culminating in the acquisition of Paragon Legal in 2018.

When she’s not working, Jessica enjoys spending time with her two nephews and her dog, Sato, as well as playing tennis, hiking and traveling.

Anna Marie Armstrong
Senior Director of Recruiting & Attorney Development
Anna Maria

With two decades of experience, Anna Marie Armstrong is an expert in the legal recruiting industry. She appreciates the value of developing long-term relationships. She thrives on the prospect of finding the very best talent for her clients and new, rewarding, and ultimately, better opportunities for her candidates. A lawyer herself, Anna knows first-hand that these opportunities don't always come easy, particularly for women and minorities. She has always made it her practice to reach out to and be receptive to lawyers who are underrepresented. She has spoken at legal conferences and top law schools about diversity as well as many other cutting-edge issues affecting the legal market.

Anna graduated from Brown University with a B.A. in English and American Literature and received her J.D. from U.C. Berkeley School of Law where she served as an Associate Editor of the California Law Review. She clerked for the Honorable Earl B. Gilliam on the United States District Court for the Southern District of California and then joined the highly-regarded firm, Howard, Rice, Nemerovski, Canady, Falk & Rabkin (merged into Arnold & Porter's San Francisco office), where she worked as an associate on complex litigation matters.

Anna began her legal recruiting career at Major, Hagen & Africa (now Major, Lindsey & Africa). She also worked at Mlegal Consulting, Mestel & Company and Hire Counsel. Anna is very well connected in both in-house and law firm circles in the San Francisco Bay Area and across the country. Her recruiting background spans the placement of associates, partners, in-house counsel, general counsel and high-level contract attorneys. She has placed in-house lawyers in the technology, biotechnology, energy, financial services, entertainment and non-profit sectors. She has expertise in both retained and contingent search.

When she is not working, Anna enjoys spending time with her young daughter. They live in Palo Alto, Anna's hometown, and are often out and about swimming, playing basketball and attending school and cultural events.

Tracy Scanlan
Director of Client Development & Legal Affairs
Tracy Scanlan

Tracy Scanlan brings a unique perspective to her role as Paragon Legal’s Director of Client Development and Legal Affairs. As a former litigator, Tracy can relate to (and empathize with) the day-to-day life of a lawyer. She’s also worked extensively in project management and business development, giving her insight into what businesses need to succeed.

Tracy really enjoys the challenge of matching one of Paragon’s many talented lawyers with just the right client. Finding this “fit” is important for the company’s multitude of ongoing business relationships, as well as for its lawyers, who offer a variety of expertise and interests. A mother of two young children, Tracy is a strong advocate for parents remaining in the workforce in a meaningful way after they start a family, and she’s thankful to work at a company that shares her philosophy.

Tracy was raised in Southern California before moving to the Bay Area to earn her B.A. in Social Welfare at University of California, Berkeley. Tracy received her J.D. from University of California, Hastings College of the Law, where she was very involved with Moot Court Competitions.

Tracy spends most of her free time with family and they can often be found exploring the Bay Area’s redwoods, museums, and restaurants. The Bay Area’s open-minded, educated but laid-back atmosphere is an important aspect to why Tracy calls the region her home.

Jennifer Chou-Green
HR Manager
Jennifer Chou-Green

Helping people achieve their full potential is what drives Jennifer Chou-Green. A human catalyst, she thrives on enabling others to become their best selves and eliminating obstacles to success for Paragon's attorneys—through comprehensive human resources support that includes benefits, onboarding, and compliance issues. Her lifelong fascination with the biology of the brain and its relationship to behavior led her to pursue her education in neuroscience, and her research has been published in several peer-reviewed scientific journals. This experience, along with her professional work as a writer and editor, shaped the tremendous analytical abilities and exceptional communication skills she brings to our team.

Yet, it's Jennifer's character that sets her apart. She's perpetually seeking new ways to contribute to something bigger than herself and assist others in fulfilling their visions. That's why she went on to the non-profit sector, where she shaped mentoring programs for young scientists and engineers at MentorNet. It's also the inspiration for her consulting practice, through which she continues to serve the scientific community as an editor of academic manuscripts and communications. Jennifer sees Paragon as a dream come true because it feeds these same ambitions while promoting a work-life balance untenable as a scientist. Her appetite for excellence extends beyond work as well. A self-confessed foodie, she's at the Ferry Plaza Farmers Market every Saturday at 8 a.m. sharp to beat the crowds to the best local produce. She holds a B.A. and Ph.D. from the University of Pennsylvania, and completed her postdoctoral fellowship at UCSF.

Gwendolyn Guerra
Operations Manager
Gwendolyn Guerra

Part business guru, part behind-the-scenes producer, Gwendolyn Guerra spends most of her time helping others succeed. She is the consummate teammate, happiest in service of the common goal. Her mission is to make work easier for everyone else by keeping operations running flawlessly—whether that's coordinating an event, improving processes, or guiding strategic decisions. And for Gwendolyn, the only way to do that is to live and breathe the business first. Because making the best accounting, HR, marketing, and growth planning decisions for a company means you need to understand the big picture. But we also know it's her gift for connecting with people that makes her so valuable as our operations manager.

This secret recipe might owe to her early career in events and public relations for some of the country's finest restaurants. Gwendolyn got her start at the San Francisco institution La Folie and went on to be the business manager for a Manhattan firm that represented restaurants and celebrity chefs, before returning to help open longtime SoMa favorite Maya. Her passion for food and strong sense of community may have also been seasoned by the cultural joie de vivre she quickly embraced while living in France. She honed her chops and management experience for over 10 years in marketing and business operations roles before joining Paragon, most recently serving as the director of accounting and human resources for Cartelligent, the largest new-car-buying service in Northern California. She holds a B.A. in international relations, which she studied at both U.C. Davis and L'Institut d'Etudes Politiques in Lyon, France. You'll often find Gwendolyn shuttling her young daughter between activities, jogging at Land's End, or trying to figure out which new San Francisco restaurant to try next.

Looking to ramp-up your in-house legal resources in an efficient, low-cost manner? Contact us.