Sheri Middlemas
Sheri Middlemas is the Chief Operating Officer of BERTOLINO LLP, where she has overseen firm operations, strategic growth, and organizational development for over seven years. With nearly 20 years of experience in legal operations and leadership, she has built a career centered on optimizing performance, strengthening compliance-driven processes, and guiding firms through sustained growth. She is recognized for her ability to translate complex legal and regulatory environments into scalable operational systems that improve efficiency while maintaining a strong client-centered focus. From an early age, Sheri aspired to become an attorney, growing up in the Washington, D.C. area with a deep appreciation for the courtroom environment and the discipline of law. While she initially envisioned a traditional legal career, her professional path ultimately led her toward the operational and strategic side of the legal industry, focusing not on why the law works, but on how organizations can be built to execute it more effectively and at scale. Over the course of her career, she has worked under a range of managers and leaders, with experiences that shaped her belief that true leadership is not defined by title, but by influence, trust, and the ability to elevate others. That philosophy has guided her approach to leadership development and organizational culture. Sheri has created and implemented mentor based leadership programs designed to help individuals understand and develop authentic leadership capabilities, an initiative she has carried across multiple organizations. She actively develops and shares leadership insights, often referred to informally as “Sheri-isms,” through internal communications and public commentary, emphasizing that leadership principles apply across industries and roles. While her firm has experienced significant growth, including more than 200 percent expansion in a recent quarter, she considers her greatest success to be the long-term impact on individuals whose careers she has helped shape. For her, the most meaningful measure of leadership is not organizational scale, but the lasting development of people who go on to lead others.
• Mental Health First Aid
• St. Petersburg College - AS, Paralegal
• Excellence in Workplace Culture Award, Small Business 2023
• Top Producer 2004
• Top Producer 2003
• Association of Legal Administrators (ALA)
• Austin Chapter of the Association of Legal Administrators
• USA Triathlon
• Kennedy Law Racing
• Florida Notary Association, Inc.
• Guardian ad Litem Program
• Florida 6th Judicial Circuit Guardian ad Litem Program
• Association of Legal Administrators (ALA)
• Association of Legal Administrators, Austin Chapter
What do you attribute your success to?
I attribute my success to understanding what true leadership means and having the ability to influence and develop leaders. Through my career, I've had fantastic managers, a handful of good leaders, and one fantastic mentor who taught me that leadership isn't about having a title - it's about being someone people trust and gravitate to. I learned early on that just because something isn't done my way doesn't mean it's the wrong way, which helped me balance my Type A personality. I organize my day by what I call 'priorizing' - organizing by priority - and when that doesn't work, I deal from the 'have-to,' focusing on what's absolutely detrimental if it doesn't get done. But what really drives my success is my passion for bringing people up and helping them understand leadership. I've created mentor leadership programs at multiple firms, and what means the most to me isn't the 200% growth we've achieved, but the LinkedIn messages from people I worked with years ago thanking me for the impact I made on their careers. That's the footprint I want to leave - making a difference in someone else's life by helping them become better leaders.
What’s the best career advice you’ve ever received?
Over the course of my career, I’ve had the good fortune to learn from many talented professionals. One piece of wisdom has echoed in my mind more than any other, and it came from a mentor who left a lasting impression on me, let's call him George. George has a way of cutting through the noise and getting to the heart of things. One day, in a conversation that probably seemed routine at the time, he shared a line that would shape the way I approached my work from that moment on: “Focus on the outcome, and the income will take care of itself.” At the time, it struck me as good advice. Over the years, it’s revealed itself as a guiding principle, especially when it comes to client service and long-term success.
What values are most important to you in your work and personal life?
The most important values to me are having a passion for what you do and making an impact on others' lives. I tell my kids that I don't care what they aspire to do, but if they can do something they have a passion for, that's a happy life. It's not going to be sunshine and roses every day - you'll run into issues, that's life and adulthood - but if you can wake up and be excited about what you do, it will make you so much more productive and help you have the impact you want to have. Your family life and your personal and professional life will all have so much more value if you can do something you're passionate about. I believe in figuring out how to make money at what you love to do. Beyond passion, I value people who come with innate skills - being on time, respectful, and having strong values. Those are things that can't really be taught, but everything else can be. I also believe that just because something isn't done my way doesn't mean it's the wrong way, which helps me balance my Type A personality. Ultimately, what matters most is the difference you make in people's lives - that's the footprint I want to leave.