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

New York Life | March 28, 2024

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

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).

Oakley says the best career advice she has received is to say “yes” to opportunities. “The Chief of Staff role wasn’t something I’d ever considered. I didn’t know what it would entail. But I was ready to try something new and I’d enjoyed working with Todd before, so I said ‘yes.’ I’m very happy I did as it became one of my favorite roles,” she says.

When she’s not in the office, Oakley, who lives with her husband and two kids, ages 6 and 4, in New York, spends most of her time with her family, which usually means chasing the boys somewhere. She’s also a big Peloton rider and crossword puzzle enthusiast.

Life Insurance Solutions is a key part of the company’s Foundational Business, responsible for product development and management, strategy, third-party distribution and operations, and inforce optimization of the retail life product portfolio.

A typical day in the life of Alyssa Oakley:

6:50 am:

“I get on the train and arrive in NYC at around 8:00 am. I like to get to the office early, because that’s my sacred and productive ‘focus time’ before meetings begin.

10:00 am:

I’m in meetings for the next couple of hours – with my team, and various 1:1 meetings with colleagues. I make the most of being in the office, scheduling 30-minute ‘coffee chats’ to connect with current and former teammates and colleagues from my peer groups, like the TWI Peer Leadership Circle. That peer group happened a few years ago, but I’m still in touch with several members.

12:00 pm:

I grab a friend and head to lunch.

1:00 pm:

I have more meetings after lunch. These tend to be project updates and team meetings.

4:00 pm:

I get back on the train. I use my train time as productively as I can by catching up on emails and work, so I’m ready for the next day.

5:00 pm:

I pick up the kids from aftercare and we head home.

6:00 pm:

From this point on, it’s family time, although I do try to squeeze in a little me-time at some point in the evening with a ride on the Peloton or catching up on TV with my husband.


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Media contact

Kevin Maher
New York Life Insurance Company
(212) 576-7937