THE A-TEAM
Meet The A-Team
Our financial advisors bring the experience and dedication to guide every stage of your financial journey.
John Thomas Swailes II
Founder & Owner
John is the founder of Pineland Investment Group. After 5 years' experience in financial advisement and leadership with a Fortune 100 company, John launched a private firm dedicated to supporting both active military and veterans with the services they deserve.
John McCaffrey
Partner, Wealth Management Advisor
John partnered with Pineland Investment Group at its inception. He began his career at a Fortune 90 company before transitioning to an independent model. With nearly five years of experience in wealth management, John specializes in helping individuals and families prepare for retirement through comprehensive financial planning and personalized investment strategies.
James Cooney CFP®, ChFC®, CLU®, FSCP®
Financial Planning Analyst
James brings deep technical expertise in financial planning to the A-Team, supporting complex analytics and strategy development for our clients.
Cassy Swailes
Client Management Services
Cassy ensures a smooth and personal experience for every client, managing our operations with precision and a commitment to service excellence.
Let's build your plan.
Tell us a little about your goals and a Pineland advisor will be in touch. No pressure — just a conversation about your future.