Women are making waves in law – sometimes quietly, at times powerfully. Disruptive legal strategies aim to private ultimate client satisfaction through an approach rooted in precision and experience while questioning long-standing norms. One such experienced attorney is Jenna Cutler, an associate at Barclay Damon LLP in New Haven, Connecticut. Her impact is felt in the confidence she inspires, the barriers she breaks and the new standards she sets for what thoughtful, forward-looking legal leadership truly looks like.
Guided Growth
Steady growth across respected litigation practices has defined Jenna Cutler’s career, shaped by guiding principles centered on continuing education and professional development. As in many demanding professions, continuing to learn throughout a legal career – not just in its earliest stages – is essential for becoming an effective attorney, both for the firm and especially for clients. That belief has consistently influenced Jenna’s professional decisions and remains a throughline in how she evaluates each new opportunity.
The legal profession is not one where practitioners master their craft in a year or two. It requires sustained dedication and long-term commitment not only to the matters at hand but also to developing the capacity to think critically, reason logically and understand the broader context that affects clients and their interests. Those skills evolve gradually, strengthened by deeper exposure to the law, the businesses and individuals attorneys represent, and to society at large. For Jenna, growth has always been measured over time, not in quick milestones.
Her first transition was driven by a desire for increased courtroom exposure and more hands-on litigation experience. That move delivered exactly what she sought. There she practiced insurance defense, an area known for heavy caseloads and broad exposure to all stages of civil litigation. The pace and volume of work often create meaningful opportunities for younger associates to operate independently, not only based on ability and development but also out of necessity to keep cases progressing efficiently.
With greater courtroom experience and litigation confidence, she moved to another firm to focus on medical malpractice, an area she had long been interested in. The firm is widely regarded as the gold standard for medical malpractice in Connecticut, and she was eager and fortunate to learn from some of the field’s most accomplished practitioners. That transition was motivated less by workload or scope and more by a desire to deepen her experience in a challenging and complex practice area she genuinely enjoyed.
This move was guided by yet another growth opportunity.
“I saw an incredible opportunity to work with a partner at Barclay Damon who would continue to advance my legal skills both in and out of court – who would help me grow as an attorney for clientsand overall as a better person,” she says.
Lizz Acee embodies the qualities of an ideal mentor: patient, knowledgeable and graceful, with a distinguished career of her own. She consistently makes time to provide guidance, whether on client matters or professional growth. As Jenna considered her long-term path and future partnerships, learning from and growing alongside Lizz was a clear and compelling choice that many at Barclay Damon would readily share. It felt exactly right.
Strategic Alignment
Delivering legal solutions that are both technically sound and aligned with business objectives has become a defining part of Jenna’s approach as an associate at Barclay Damon. The firm operates with a level of transparency among partners, counsel and associates that allows attorneys to understand the bigger picture for clients earlier in their careers. Rather than being brought into matters in piecemeal, younger associates are involved holistically, supporting steady growth in legal skills while fostering a deeper understanding of each client.
In litigation especially, Jenna Cutler recognizes that the “best” decision is not always dictated solely by the law. Outcomes are often shaped by the ultimate goals and practical needs of a business or individual client. Effective legal strategy, therefore, requires more than a command of black-letter law; it demands a working knowledge of the client, the industry and the realities influencing decision-making.
Her process begins with a foundational consideration: the client’s ultimate objective. From that starting point, she focuses on researching and analyzing the applicable law to develop options. Her role is to support partners and clients by presenting the best possible options to achieve those goals while remaining within legal boundaries, ensuring strategic solutions are informed and aligned with the client’s vision.
Collaboration Without Boundaries
Working across multiple firms and legal environments has given Jenna a perspective on what distinguishes Barclay Damon’s collaborative, multi-office model in meeting client needs. Barclay Damon operates nine offices across the Northeast, as well as in Washington, D.C., and Toronto. The firm’s holistic approach is unique in Jenna’s experience.
Many firms define collaboration through an open-door policy or by offering associates chances to work with partners and counsel in other practice areas. Barclay Damon embraces those practices but also commits resources to ensuring that partners, counsel and associates know one another and understand the skill sets that are available across offices.
A clear example of this commitment is the firm’s attorney retreats. While not mandatory, participation is encouraged. These gatherings allow attorneys to spend time with colleagues from other offices and learn how they practice. That familiarity strengthens client service.
“If I have a labor and employment client, the relationships I have built across the firm help me spot opportunities to bring in colleagues for related needs – mergers and acquisitions, tax issuesor cross-border work for clients looking to expand into the United States,” Jenna says.
Strategic Precision
Balancing rigorous legal analysis with the adaptability required in complex, high-stakes litigation has become central to how Jenna approaches her work. One of the most underrated skills in litigation, she believes, is creativity. The law itself can be fickle. Certain aspects – often rooted in black-letter law – demand strict adherence to precise language. Other areas, particularly in litigation, exist in gray spaces that allow room for argument and for interpretations that are new or less frequently tested. Effective advocacy requires using both with intention.
A strong litigator must respect the rigid, unforgiving elements of the law while also working with the facts to reach the most efficient and effective outcome for the client. In some matters, that balance means crafting a creative legal argument. In others, it involves identifying a path toward resolution with opposing counsel that may include both monetary and nonmonetary solutions.
Rigorous legal analysis remains essential in every case and serves as the foundation for strategic thinking. No two matters present identical factual backgrounds. Through extensive research examining what the law says and how courts have interpreted it, Jenna draws from related cases to build arguments that fit the situation at hand. The result is advocacy that is persuasive, sometimes innovative and – when it departs from tradition – compelling.
Future Advances
Developing the next generation of legal professionals is a responsibility Jenna takes seriously, particularly as modern litigation continues to evolve. Jenna Cutler recognizes that the legal community does not always fully appreciate the importance of those coming up behind today’s leaders. The profession is known for partners, judges and senior attorneys continuing to practice late into their careers and lives. While learning from those leaders remains critical, Jenna believes equal attention must be given to engaging and preparing the generation that will follow them.
The legal field itself is constantly changing, even if that change often comes more slowly than in other industries. COVID-19 accelerated that evolution dramatically. Hearings are now largely virtual, and AI is increasingly used for first drafts and foundational research, even if only as a starting point. The next generation has grown up immersed in technology, often with a level of comfort that prior generations may not share or seek to develop. Equally important is this generation’s reluctance to resist change simply to preserve tradition.
In her work as a mock trial coach, the rules of evidence and courtroom etiquette formed the foundation of instruction. But Jenna also made space for honest conversations about career paths – what options exist and which opportunities might align with individual goals. For aspiring litigators, mock trials build essential skills: thinking on one’s feet, public speaking and pushing through an argument even when it falters.
“Those skills are not taught through a book. They are learned through trial and error,” she says.
Students also need to understand that no attorney is perfect, and perfection is rarely expected. What matters is that they learn to extend themselves grace when something falls short, learning from it and continuing to grow from the experience.
Practice Molds Perspectives : –
A career spanning private practice, public interest work and academic engagement has shaped her perspective on the broader role attorneys play in society. Her professional philosophy is rooted in the belief that education is essential to understanding and advancing society. Exposure to multiple sectors of the law has allowed her to keep learning and to appreciate viewpoints she would not have encountered had her career remained confined to a single area.
That range of experience also enables Jenna to share insights with colleagues at Barclay Damon and within the legal community more broadly. She believes successful attorneys must remain creative, open-minded and willing to consider perspectives beyond their own to provide clients with comprehensive advice and a full range of options.
In reality, the private sector, public sector and academia are deeply interconnected. Viewing them in isolation limits progress for everyone involved. To advance the law, serve clients’ interests effectively and continue growing as an attorney, she sees value in engaging with as many perspectives as possible.
Strategic Litigation
Advising clients to view litigation as more than just a legal issue has become a central part of her approach, particularly in cases defending companies. She notes that clients often instinctively become defensive when facing allegations, wanting to protect their name and reputation. That response is natural and morally understandable, yet it is not always the most strategic business decision.
Jenna Cutler emphasizes that refusing to pursue a reasonable resolution under the belief of “I didn’t do anything wrong, so I shouldn’t have to pay” can end up costing a company far more. That does not imply that every claim should be settled or that every case must be fully litigated.
“A lot of the conversation involves helping clients weigh the reality that they may not have done anything wrong against the cost of multiyear litigation and the possibility that a judge or jury could still disagree,” she says.
Some of the most challenging conversations involve encouraging clients to set aside pride – a step lawyers themselves take when necessary – to ensure the best overall outcome for the business.
Excellence With Grace
Maintaining excellence while keeping perspective has been a guiding focus for Jenna, particularly in the early stages of an attorney’s career. She acknowledges that imposter syndrome is a natural and often expected experience for younger associates. Fresh out of law school, many are thrust into situations demanding quick thinking, instinctive responses and mastery of applicable law – all especially pronounced in litigation.
Jenna emphasizes the importance of retaining perspective: recognizing where one has come from, understanding the present and keeping sight of future goals. Equally essential is operating with grace. No attorney – associate, counsel or senior partner – is perfect, and most errors in litigation can be corrected. Mistakes may be frustrating or embarrassing, but they are part of the professional journey.
What matters most, she notes, is learning from errors and applying those lessons moving forward. Making mistakes does not define an attorney’s capability; failing to learn from them does. She believes younger associates must understand early that they can achieve excellence without achieving perfection.
Inclusive Leadership
Her engagement with the Leadership Council on Legal Diversity Pathfinders initiative and bar associations has significantly shaped her approach to leadership and client relationships. She observes that lawyers are often placed into leadership roles simply by the nature of their work. Clients rely on attorneys to guide them on matters that can profoundly impact both their personal and business lives, placing trust at the center of the attorney-client relationship.
Yet law school alone does not equip attorneys with all the tools needed to guide clients most effectively.
“Each organization I have been part of and each leadership role I have been thrust into has given me different tools to pull from – whether I am working with clients, mentoring law students or mentoring younger associates,” she says.
LCLD brings together attorneys from groups that have historically been overlooked, marginalized or disadvantaged based on inherent characteristics. Jenna notes that her experience with the organization has reinforced the importance of listening to voices not always centered in the profession and integrating those perspectives in both leadership and advocacy, ensuring that her growth as a lawyer is informed, inclusive and effective.
Adaptive Advocacy
Jenna Cutler believes that adaptability and creativity will define successful litigators in the coming decade as the legal industry continues to evolve with shifts in client expectations, technology and regulation. She notes that while the legal field often grows slowly and clings to tradition – sometimes at the expense of broader progress – technology is accelerating change, whether the industry is ready or not.
A litigator who excelled 10 years ago but struggles with Zoom, e-discovery platforms or other emerging tools will find their effectiveness diminished. Attorneys must be able to adapt to new technologies, evolving societal expectations and even arguments that may once have seemed unconventional or improbable.
Jenna Cutler emphasizes that long-standing legal principles remain vital. Successful attorneys will continue to draw on decades of established law while leveraging modern tools to work more efficiently. As technology advances, client expectations evolve in parallel. Today, clients – particularly large corporations – expect attorneys to employ contemporary tools effectively, delivering robust legal guidance while managing costs where technology allows.
Industry Insight
Jenna Cutler emphasizes that industry knowledge significantly enhances the effectiveness of litigation strategy. In certain areas of law, outcomes can vary depending on the client’s industry, making it essential to understand the specific business context of those being represented.
“Industry knowledge helps you evaluate risk more realistically, understand how decisions will land internally for the client, and build arguments that fit the operational reality of the business rather than just the legal theory,” she says.
Jenna Cutler notes that a deep understanding of clients’ industries provides a broader perspective on their legal concerns and questions. It also enables consideration of factors that attorneys without such insight might overlook, ultimately strengthening strategy and client outcomes.
Community Builds Confidence
Mentorship and professional community have been central to her career, shaping both her confidence and competence in the practice of law. She notes that litigation often demands that lawyers present a facade. Younger attorneys are expected to carry themselves with the wisdom and maturity of senior partners, while attorneys from marginalized communities may feel additional pressure to outperform simply to prove they belong. After all, clients expect answers, and it is what clients believe they are paying for.
“Often that pressure forces lawyers to put aside fears, concerns or even successes for the sake of providing what courts and clients expect,” she says.
Jenna Cutler observes that professional communities are among the few spaces where attorneys can connect with like-minded peers, work through internal struggles, and find understanding and comfort. These networks help alleviate imposter syndrome, offering opportunities for mentorship with attorneys who not only sympathize but also empathize. Through these connections, attorneys can better recognize their own value, name their strengths and address weaknesses without fear of judgment.
Professional communities also offer practical benefits, providing attorneys with opportunities to build trust, deepen relationships and create referral networks with colleagues who know and respect their work. She encourages all attorneys to find a professional home that fosters growth; law is not a career meant to be navigated alone. For her, LCLD, the National LGBTQ+ Bar Association, the Connecticut Bar Association and the American Bar Association have each supported different facets of her identity while providing safe spaces to learn from and share with peers in similar circumstances.
Purposeful Litigation
Jenna Cutler reflects on the moments that have most reinforced her commitment to litigation, acknowledging that it is a demanding area of the profession. The work often involves long hours and projects arriving at the last minute. Success requires dedication not only to legal expertise but also to continually developing skills such as public speaking and legal writing, along with emotional intelligence – an often-overlooked but essential component.
Jenna Cutler’s initial inspiration came from competing in a mock trial during law school, an experience that later motivated her to coach students so they could share that same learning. Many litigators thrive on competition, and professionally, there is a unique validation and euphoria in winning an oral argument. Months or even years of preparation culminate in recognition of their hard work, motivating them to endure long hours, challenging cases and inevitable losses.
Litigation, however, is about far more than personal victories. It can have meaningful impacts on clients and communities. She helped establish a free legal clinic for Connecticut’s LGBTQ community during a time of rapid political shifts, offering guidance and representation that clients could not achieve alone. The gratitude from those served and the ability to provide clarity and comfort have reinforced for her the profound significance and purpose of litigation work.
Connected Growth
Jenna Cutler advises that the most important step for young professionals, particularly those early in their legal careers, is to get involved. For her, that involvement has been through bar associations, especially the Connecticut and American bar associations, but it need not be limited to professional organizations. Many find growth and success through community engagement, whether coaching youth sports, participating in local politics, volunteering or staying connected to organizations from law school.
“The important part is continuing to meet new people, learn new perspectives and expose yourself to new opportunities. Bar associations have been immensely helpful for me. I have met people – often attorneys, but not always – from across the country who approach both the law and life differently than I do,” she says.
Lessons learned from those relationships can be brought back to her work at Barclay Damon. She also highlights young lawyer sections as especially beneficial, offering candid insight into what is working across firms and the direction of the profession.
Jenna Cutler stresses that building a meaningful, impactful practice cannot be done in isolation. It requires community, perspective and relationships that continuously expand the understanding of what is possible.
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