A Day in a New York Life: Life Insurance Solutions’ Alyssa Oakley.

The Day in a New York Life article series offers a look into the daily lives of employees: what they do, their career paths, what they find most interesting about their jobs, and how they spend their time outside of the office.

Alyssa Oakley wears many hats. Until February, she was head of Digital Marketing in Retail Annuities and chief of staff to Todd Taylor, who was then head of Retail Annuities. Then, when Taylor became head of Life Insurance Solutions, Oakley moved with him, taking on the role of head of Strategy and Business Planning, in addition to keeping chief of staff responsibilities.

As head of Strategy and Business Planning, Oakley helps define short- and long-term strategic priorities for Life Insurance Solutions and tracks progress toward those priorities throughout the year. She also works on such cross-functional projects as defining the long-term strategy for third-party distribution in Life Insurance Solutions and partnering with teams inside Life Insurance Solutions and across the company (e.g., collaborating with the Service Experience Value Stream to identify opportunities to enhance retention for our life insurance products).

As Chief of Staff, Oakley provides strategic support to Taylor, which includes preparing for presentations and meetings with agents and third-party distribution partners. As a member of the Life Insurance Solutions Leadership team, she plans meeting agendas to ensure the team is discussing key priorities. She is also responsible for initiatives to drive employee engagement and professional development within Life Insurance Solutions. 

Oakley didn’t see herself working at an insurance company. In fact, for many years, she trained as a classical ballerina. Her focus shifted to engineering in college, and while she chose not to work as an engineer, she enjoyed the coding and problem-solving aspects of the coursework. She leveraged those skills in digital marketing and strategy roles across a variety of industries for the first 10 years of her career, and in 2019, she joined New York Life’s Retail Annuities Marketing team.

“I’ve had the opportunity to learn so much about our business and work with many different teams. Plus, I really love the people and culture,” says Oakley. “The most rewarding thing about my job and working here is the relationships I’ve developed. Being part of TWI [The Women’s Initiative employee resource group] has been another great way to meet people across the company.” (Oakley serves on the TWI core leadership team as communications co-lead).

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