Updated March 28 at 6:28pm

Five Questions With: John Olerio

Senior vice president and regional sales manager at Webster Bank talks about his recent recognition from Bank Investment Consultant, which named him to the list of Top 20 Program Managers for 2014.

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Five Questions With: John Olerio


John Olerio is a senior vice president and regional sales manager at Webster Bank and is responsible for overseeing Webster Investments, including the Webster Retirement Plan Division.

Olerio has been a financial professional for 27 years. He is a FINRA Registered Representative with a Series 7/65 and a Registered Principal with a Series 24 with his broker/dealer LPL Financial, member FINRA/SIPC.

Olerio has a bachelor’s degree in economics from Boston College and a master’s degree in financial management from Carnegie Mellon University.

PBN: The recognition you earned from the financial services industry magazine Bank Investment Consultant, being named to the list of Top 20 Program Managers for 2014, confirms you have strategies and practices that make you stand out in your industry. Can you list two or three of the guiding principles you use daily in your work that helped you earn this recognition?

OLERIO: Coaching and mentoring our team of Financial Consultants at Webster is my top daily priority. We have a disciplined business planning process in place for every team member and work together for successful execution. Daily awareness of market conditions and economic climate is also important as is internal networking within Webster Bank with all business lines at Webster bank to promote cross sell and partnership.

PBN: The recognition was based on several factors, including average production per advisor and percentage of growth of team assets from the previous year. How many members do you have on your team? In the highly competitive environment in the financial services industry, what strategies do you use to increase your production, as well as the production of members of your team?

OLERIO: We currently have 56 financial consultants across Webster’s four-state footprint in Connecticut, New York, Massachusetts and Rhode Island. We differentiate ourselves from the competition through our personalized approach to live up to the needs of each individual client. Together with our clients, we aim to manage, grow, and protect their wealth. Our industry-leading sales growth emanates from our disciplined business planning approach to grow market share with existing clients, as well as to consistently cultivate new clients. Our most successful area of growth in both areas has been through our focus on retirement planning for new and existing clients.

PBN: You’re based at Webster Bank offices in Wallingford, Conn. and live in North Kingstown, so you’re well aware of Rhode Island’s more sluggish economy. Do you see differences in your business and your potential business in the two states, or with Rhode Island in comparison to other states in your territory?

OLERIO: I was born and raised in Rhode Island and have continued to commute several hours a day, three-to-four days a week, for the past 17 years. The economic struggles in Rhode Island exist throughout our geographic footprint and require that we be responsive, proactive and entrepreneurial in order to grow our business. I must say that Rhode Island and southeastern Massachusetts have been very successful areas of business for Webster over the past 10 years. In fact, the Rhode Island and southeastern Massachusetts area has been our fastest growing territory for Webster Investment Services over the past two years.

PBN: As regional sales manager for Webster Investment Services, what are you finding to be your clients’ most common preferences as far as investments – long-term, short-term, high-risk, low-risk? Do you anticipate this changing in the next couple of years?

OLERIO: The most important area of focus for our clients is retirement planning. This is obviously a long-term goal for most, but unfortunately, it can be a short-term priority for those who begin the planning process later in their working career. Retirement planning needs to incorporate the risk profile of each client, and the majority of clients have become increasingly concerned about risks associated with their retirement nest egg. However, clients are also increasingly concerned about low- or no-growth of their retirement assets. Balancing the risk and return wish lists has been, and will continue to be, a big challenge facing our clients planning for, and living in, retirement.

PBN: Are your clients tending to change in any way, as far as age, geography or socio-economic level? In other words, are those who invest tending to be the same groups you’ve worked with in your years of experience, or are you seeing any changes in types of investors?

OLERIO: At Webster, we continue to grow most successfully in the “mass affluent” space. In the most basic sense, the mass affluent tend to have an above-average income, are forward-thinking from an economic standpoint and have an above average number of liquid assets. Our customized approach to individual clients seems to resonate strongly with this particular segment. We are especially focused on helping clients with 401k accounts who are approaching retirement. These are clients in need of guidance on making their nest egg as productive as possible during their retirement years. We take the time to listen and understand our client’s needs, and together, we develop solutions. We strive to live up to the expectation of our clients for honesty, integrity and excellent service.


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