2025 Top Retirement Plan Adviser: Christopher Connolly

This year, PLANADVISER followed up with advisers on the 2025 Top Retirement Plan Advisers listing to get to know them better. These are the responses from Christopher Connolly of Retirement Team at CANE in Braintree, Massachusetts.

PLANADVISER: What are the most challenging aspects of the job? What are the most enjoyable?

Connolly: One of the most challenging aspects of our work is the sobering reality that many Americans are simply not prepared to retire. There are countless reasons why—some are within their control, many are not. While all of us in the industry would love to see every participant retire with financial security and dignity, we know that is not always the case. In fact, the gap between retirement readiness and retirement reality seems to grow more visible every day.

But on the flip side, one of the most rewarding parts of this job is witnessing the success stories—people who have stayed the course and now face retirement with confidence.

I am thinking of one of my closest friends in the industry. She entered the retirement space almost by accident at age 45. Recently divorced, raising five kids and with no savings to speak of, she could have easily felt overwhelmed. Instead, she got serious. She “drank the Kool-Aid,” as she puts it, and committed to saving—consistently.

She did not take on more than she could afford. She did not aim for a grand slam. What she did was increase her savings each year she could, even if only by 1% or 2%. She never took a step backward, and she was intentional about how those savings were invested. By age 68, she could have retired comfortably. She chose to keep working until 70 to maximize her Social Security benefit—replacing zeros from her early years with higher-income credits at the end.

That is the kind of outcome we strive for. Not every story starts perfectly, but discipline, time and support can still lead to a great ending. We have plenty of stories like hers—but we want more.

PLANADVISER: What does it take to be a successful retirement plan adviser in 2025?

Connolly: Now, more than ever, it is important that everything you provide your participants is optimal. Doing so provides your participants with the chance of the retirement they want. All aspects of what we deliver have the participants’ end results in mind, whether that be in working with them directly or via the plan sponsor. We attempt this through:

• Outcome-focused plan design – stretch matching programs, automatic enrollment, automatic escalation and safe harbor matching programs, to name a few;
• Fiduciary advice – guiding the fiduciary group through the various regulations and ensuring compliance throughout;
• Participant engagement – providing relevant presentations, such as 401(k) Roth myths, as well as one-on-one participant advice and retirement income gap analysis;
• Investment advice – both at a plan sponsor and participant level;
• Plan benchmarking – utilizing tools such as fiduciary decisions to ensure our plans are incredibly competitive when compared with others of the same size throughout the country;
• Industry knowledge – building and maintaining strong relationships with vendors to ensure we are up to date with every offering to deliver the right fit for each client; and..
• Measuring results – we want to deliver on all aspects, including investment advice, educational programs and one-on-one advice, but we also want to understand how these deliverables increase plan health and how to affect each group where needed.

Put simply, our overall goal is not only to ensure all variables are optimal, but to allow each participant to have a plan. We want everyone to be aware of how on track they are … or are not at this time. We believe that when participants understand how on track they are for the retirement they want, it will impact day-to-day decisions. That knowledge will positively impact their probability of success.

PLANADVISER: Has the focus or character of your practice shifted meaningfully over time to respond to evolving client demands, market pressures or the emergence of new technologies?

Connolly: I do not believe the focus of the firm has changed, as it has always been focused on the individual. We provide fiduciary advice to the plan sponsor and participant groups with the guiding light being participant outcomes. How do we get them to the finish line and retire with dignity? The meaningful shift has come in the way of deliverables, the utilization of new applications and technology to allow the participant to clearly understand where they are now and where they are headed. If the projected outcome is not what we want, how do we get there? We make retirement tangible—not just for the 60-year-old who can see it on the horizon, but for the 25-, 30- and 35-year-olds who are just starting their journey. New technology has made delivery of the necessary information much easier.

PLANADVISER: How do you balance the desire to grow with the need to keep clients happy?

Connolly: Balancing growth with client satisfaction is a challenge for any business. If you grow too fast, service can slip; if you focus only on existing clients, your practice may suffer. I like to say, ‘If you’re not growing, you’re slowing.’ We have all encountered a client being purchased by a larger corporation and your plan being swallowed up by the purchasing group. I hire when it is absolutely necessary so that when declines occur, I can maintain my staff. That is very important to me. Due to that, we incorporate process into every aspect of the practice. Meeting with clients, while providing customization, is process driven and repeatable.

PLANADVISER: What is something you or your team learned the hard way about this business?

Connolly: Inertia is real!

When I hired one of my associates, Emily, a few years ago, one of her key responsibilities was to help reduce the number of terminated participants within our retirement plans. We were motivated to spare our plan sponsors the time and expense of an annual audit.

Unfortunately, removing participants with balances greater than $7,000 is far more challenging than one might expect. Despite our proactive outreach and sincere efforts to assist, inertia remains a powerful force.

Here is the language we use in our initial communication, which aims to support participants in consolidating their retirement assets:

• Roll your balance to your new employer’s 401(k)—whether you are currently eligible to contribute, you can roll in your balance.
• Transfer your funds to an existing IRA—or if you do not have one, we can help you explore suitable options.
• Take a distribution—though this is rarely advisable, and we are happy to explain why.

While we have seen some success, it has not been as widespread as we had hoped. The reality is that many participants simply do not act unless required. Consolidation of assets is just one area where inertia is a problem. We can list several others that impact our plans.

View Other Top Retirement Plan Adviser Profiles Here