Matthew T. Macklin’s professional story is one of strategic innovation. Today, he serves as Managing Attorney of Stratagem Law Group, where he leads a firm dedicated to balancing legal rigor with pragmatic business insight. But the path that brought him to law was forged not in courtrooms, but in health care.
“Health care was the family business,” Macklin recalls. “My mom was a director of nursing, and I spent time in the activities department calling bingo and decorating cookies. For me, nursing homes were full of life, not places people go to die.” That early familiarity with healthcare operations shaped his career trajectory, even if it wasn’t initially by design.
Graduating in 2009 during the housing crisis, Macklin faced a bleak job market. Graduate school seemed futile, so he returned to his hometown and trained to become a nursing home administrator. After he completed his residency, he was faced with two opportunities. He could either manage a pristine facility in Martha’s Vineyard or take over a deeply troubled center in Tacoma, Washington. He chose the latter. “It was one of the worst survey outcomes I had ever seen,” he explains. “But I built a team, and we turned it around.”
That decision defined the next decade of his career. Macklin became known for his ability to lead turnaround operations, taking on distressed facilities across the country and stabilizing them for long-term success. “Tacoma was a forged-by-fire experience,” he says, “it taught me how to manage teams in the least ideal circumstances, navigate hostel regulatory agencies, and restore organizations under immense pressure.”
While leading those projects, Macklin pursued a law degree through a demanding weekend doctoral program, commuting from Washington to Chicago every other weekend, even through the COVID-19 pandemic. The experience was grueling, but it cemented his transition from operations into law. “I wanted to marry my work in compliance to take everything and leadership and strengthen it with legal execution,” he says. Macklin’s leadership and health care background with his legal expertise make him unique in the legal world.
In 2021, Macklin launched Stratagem Law Group. From its earliest days, the firm was shaped by its belief that clients deserve a strategic partner, not the proverbial legal “no” or ”operational roadblocks”. Attorneys often default to telling businesses what they cannot do,” he explains. “My goal is to help them get to a safe yes, the most workable yes possible. That’s what being a voice of reason really means.”
Stratagem Law’s practice reflects Macklin’s broad background. Stratagem’s team provides litigation, compliance counsel, and business advisory services, but what distinguishes it is the integration of legal and practical business perspectives. “My clients often want my legal advice and my business opinion,” Macklin says. “They are not always the same, but that dual lens helps clients make more informed decisions.”
Macklin has a commitment towards equity and works within his community supporting non-profit organizations in his practice and often pro bono. His principle of building equitable community with lasting structures guides Macklin’s nonprofit work, whether revising bylaws, stabilizing boards, or helping organizations achieve good governance. “It’s the ‘teach me to fish’ philosophy,” he explains. “The goal is to leave clients and organizations stronger than before I arrived.”
Looking ahead, Macklin is developing a podcast aimed at demystifying compliance and legal issues for business and nonprofit leaders. “Most people don’t understand what it means for legal to sign off on something,” he says. “The goal is to reveal the man behind the curtain and understand what lever he is pulling. If you explain the why and the process, people are most likely to retain it, and that generates buy-in. The goal of the podcast is to assist non-lawyers and lawyers alike and be more self-sufficient. That’s the sustainable knowledge base I want to create.”
For now, his focus remains on leading Stratagem Law with the same balance of compliance, compassion, and pragmatism that has marked his career. Whether turning around a distressed healthcare facility, guiding a business through litigation, or strengthening a nonprofit board, Macklin’s approach is consistent: deliver solutions that last.
“At the end of the day, everything I do, whether in healthcare, law, or nonprofits, comes back to the same goal,” he says. “I want to do work that matters, and I want to help people succeed.”
In blending healthcare operations, legal expertise, and community service, Matthew T. Macklin crafted a career defined through impact. His story is proof that the most effective leaders are those who bring pragmatism, innovation, and humanity to every challenge they face. Macklin’s ability to address these complex issues and make them comprehensive through his expertise in both health care and law makes him and Stratagem strong players in the industry.
