Gregg Cummings, AIFĀ®, CRPSĀ®, CPFA
I'm Gregg Cummings, a Financial Planner and Qualified Plan Consultant. When I opened my own firm in 2011, I had one mission: to deliver dedicated retirement plan consulting and wealth management services to clients nationwide.
Whether you're an individual seeking financial planning guidance or a business looking to offer fiduciary-focused retirement benefits, serving clients is my passion. My background across publishing, software, and communications gave me invaluable insight into the retirement plan needs of businesses and employees at every stage of growth.
I was drawn to financial planning to help people navigate life's stages without making uninformed decisions or chasing returns without a clear goal. I listen first, then help you plan the course. I hold the AIFĀ®, CRPSĀ®, and CPFA designations.
Outside of work, I enjoy traveling with my wife Sheri, walking our dog Maui, and staying active through cycling, swimming, and hiking. I also volunteer regularly at our church and in the local community.
Lake in the Hills, IL
"What sets my approach apart is that I start by listening. My clients have told me that I ask good questions and genuinely want what's best for them. I don't believe in forcing a one-size-fits-all solution ā I believe in building a living, breathing plan that evolves with each client and their family over time.What I love most about this work is helping people get to a place where they have a plan and feel confident they're going to be okay if they stay committed to it. It's incredibly rewarding to help someone move from uncertainty to clarity and feel more secure about their future."
How can I help?
Employer-Sponsored Plans
Retirement Planning
Estate & Trust Planning
We specialize in making the often complex and emotionally charged process of trust and estate planning as seamless as possible ensuring the security and preservation of a client's legacy for future generations.
Financial Planning & Analysis
Personalized wealth management helps our clients protect their assets. We use a holistic approach to financial planning that integrates tax strategy, trust & estate planning, and risk management.
Get to know Gregg
Gregg Cummings came to financial advising through a career change after seeing that many people had retirement accounts and savings, but no real plan tying it all together. That realization drew him to this work. He wanted to help people think beyond just investments and build a clearer path around retirement, family needs, estate considerations, and the "what ifs" life brings. With more than 20 years of experience in wealth management, Gregg takes a thoughtful, client-first approach grounded in listening, asking good questions, and building a plan that can evolve over time.
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Gregg works with a range of clients, including women, families, and middle-America households, as well as small to midsize businesses with 401(k) plans. He is especially passionate about working with people who want more than just investment management and are willing to engage in the planning process. His focus areas include employer-sponsored plans, financial planning and analysis, retirement planning, and estate and trust planning.
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What sets Gregg's approach apart is that he starts by listening. His clients have told him that he asks good questions and genuinely wants what's best for them. He doesn't believe in forcing a one-size-fits-all solution. Instead, he believes in building a living, breathing plan that evolves with each client and their family over time.
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What Gregg loves most about this work is helping people get to a place where they have a plan and feel confident they're going to be okay if they stay committed to it. It's incredibly rewarding to help someone move from uncertainty to clarity and feel more secure about their future.
I came to financial advising through a career change after seeing that many people had retirement accounts and savings, but no real plan tying it all together. That drew me to this work. I wanted to help people think beyond just investments and build a clearer path around retirement, family needs, estate considerations, and the "what ifs" life brings.
I work with a range of clients, including women, families, and middle-America households, as well as small to midsize businesses with 401(k) plans. I'm especially passionate about working with people who want more than just investment management and are willing to engage in the planning process.
I focus on employer-sponsored plans, financial planning and analysis, retirement planning, and estate and trust planning. I help clients by first taking the time to understand where they are, where they want to go, and what matters most to them. From there, I help build a plan that can adapt as life changes, so it stays practical, personal, and aligned with their goals.
I focus on employer-sponsored plans, financial planning and analysis, retirement planning, and estate and trust planning. I help clients by first taking the time to understand where they are, where they want to go, and what matters most to them. From there, I help build a plan that can adapt as life changes, so it stays practical, personal, and aligned with their goals.
What sets my approach apart is that I start by listening. My clients have told me that I ask good questions and genuinely want what's best for them. I don't believe in forcing a one-size-fits-all solution. I believe in building a living, breathing plan that evolves with each client and their family over time.
What I love most about this work is helping people get to a place where they have a plan and feel confident they're going to be okay if they stay committed to it. It's incredibly rewarding to help someone move from uncertainty to clarity and feel more secure about their future.
Working with Savvy allows me to bring a comprehensive, client-first approach to every relationship. The platform supports my commitment to building plans that evolve over time, and it enables me to serve both individual clients and small to midsize businesses with the depth and attention they deserve.
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