Kevin Connors

CFP®, APMA®, CRPC®

Private Wealth Advisor & Managing Partner

Kevin’s path into financial advice began early in high school, when he had the opportunity to learn from a teacher and mentor who was a retired CFP® professional. Through that experience, he developed a deep appreciation for both the responsibility and long-term impact of thoughtful financial guidance, an influence that would shape his career.

Building on that foundation, Kevin went on to earn his Bachelor of Science in Finance from Boston College. He later obtained his CFP®, APMA®, and CRPC® designations, reflecting his ongoing commitment to delivering thoughtful, comprehensive advice across investment management, retirement planning, and long-term wealth strategy.

As Managing Partner of City Square Wealth Management, Kevin works with high-income earners, business owners, and retirees navigating complex financial decisions and seeking a more coordinated approach to their wealth. Clients value his disciplined attention to detail and his ability to identify opportunities within complex financial structures, whether that means optimizing tax efficiency, structuring retirement income, or solving for more complicated planning scenarios. His approach is proactive and deeply personal, serving as a trusted partner who serves as a steady partner as clients’ lives evolve.

Outside the office, Kevin and his wife, Kira, are busy supporting their three children in everything from hockey to dance. Between rounds of golf and morning runs, he keeps a close eye on the Boston sports scene and an even closer eye on Bruce Springsteen’s tour dates. If there’s a show nearby (or even a few states away), you can likely find Kevin somewhere in the crowd.