Kevin T. O’Connor brings a steady and compassionate presence to his work in estate planning, trust administration and probate. It’s an approach shaped by his background as a hospice social worker. He was drawn to estate planning as “a part of the law where I could work with clients to help things go smoothly rather than fighting over them.” Kevin helps SMT clients navigate emotional decisions with clarity, ensuring that plans are thoughtful, complete and easy to understand. His calm, reassuring style makes complex processes feel manageable. Outside the office, his hospice experience continues to inform how he supports families through some of life’s most meaningful transitions.

Jessica L. Alys brings a thoughtful, people-first perspective to her work as an estate planning attorney. She was drawn to estate planning because it combines “complex legal nuance with real human impact.” She focuses on understanding each client’s needs, helping SMT clients navigate decisions with clarity and care. Her approach balances intellectual curiosity with empathy, ensuring each plan reflects her client’s intentions. Having lived in five countries and speaking four languages, Jessica brings a global perspective that shapes how she connects with clients from diverse backgrounds.

Lisa Ann Hilario helps businesses navigate employment law through a distinctly human lens. Specializing in labor and employment law, she focuses on the intersection of compliance and workplace relationships, helping SMT clients build stronger organizations while navigating complex legal requirements with confidence. “Employment law allows me to focus on the human perspective, not just its complexity,” she says. Lisa Ann works closely with business owners and HR professionals to provide practical guidance that helps them make informed decisions and avoid unnecessary risk. Outside the office, she educates the community about the legal risks associated with hiring private caregivers and domestic employees.

With a strong litigation background, Kari Brown represents employers in nearly all areas of employment law and litigation, helping them navigate complex and often overwhelming situations. She brings strong analytical skills to her work, with a focus on resolution and practical outcomes. Kari describes her approach as “breaking things down into smaller digestible steps so clients can move forward with their business and with life,” even when challenges feel daunting. She is known for making difficult issues approachable and actionable. Kari has two young children and spends much of her free time with her family, often at sporting events, enjoying time together and staying active.

David Chu advises SMT clients on corporate, securities and real estate matters with a strong understanding of both legal and business realities. He works as a strategic partner, blending legal analysis with practical business insight to help clients make informed decisions. As he puts it, “You can be on solid legal footing, but that doesn’t always make it the best business decision.” David helps clients balance risk, cost and opportunity to achieve real-world results. Outside the office, he enjoys playing chess, a pursuit that reflects his ability to anticipate challenges and think several moves ahead.

A fierce advocate for his clients in trial and arbitration, Regan Masi is a civil litigator with extensive courtroom experience. While fully prepared to litigate when necessary,
his approach focuses on the efficient and strategic resolution of conflicts through negotiation and settlement when it serves his clients’ best interests. “My goal is to solve problems,” he says, noting that many disputes can be resolved with thoughtful conversation before going to trial. Regan works closely with attorneys across SMT’s practice areas, drawing on the firm’s broad subject matter expertise to support clients facing complex legal disputes. A lifelong Sonoma County resident and Air Force veteran, he brings both perspective and determination to his practice.

A business attorney focused on building long-term relationships with his clients. Andrew Spaulding began his career in litigation before shifting to business-focused work to emphasize collaboration and shared outcomes. “I value relationships that last decades, not just transactions,” he says. Andrew takes a proactive and personal approach to understanding each client’s needs, helping them navigate change and growth over time. Outside the office, he enjoys spending time with his family and is involved in youth-oriented nonprofits—including Luther Burbank Center for the Arts and the Children’s Museum of Sonoma County— supporting arts and education initiatives in Sonoma County.

Barbara Gallagher brings decades of experience across business, real estate, trusts and estates and intellectual property law. Her practice has long focused on helping business owners navigate both professional and personal matters, often building relationships that span decades. Barbara believes effective counsel begins with listening. “What’s most important is that clients feel they were listened to and that they believe I care about what happens,” she says. Known for her thoughtful and relationship-driven approach, she helps clients see the bigger picture while addressing complex legal and strategic issues. Outside the office, Barbara enjoys hiking, Pilates, pickleball, traveling and spending time with her children and grandchildren along the Sonoma Coast.

“DJ” Drennan is a business attorney with deep experience guiding companies through every stage of the business lifecycle, from formation and growth to mergers, acquisitions and succession planning for family-owned businesses. He helps SMT clients understand complex legal issues through practical, experience-driven advice. In high-stakes M&A transactions involving multiple legal disciplines, DJ coordinates SMT’s attorneys to keep deals moving efficiently while securing strong outcomes for clients. He describes SMT’s culture simply: “We take the work seriously, but we don’t take ourselves too seriously.” Outside the office, DJ enjoys traveling, spending time outdoors and crafting the ideal cocktail.