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Updated: August 5, 2019 / 2019 40 Under Forty Awards Honorees

Orlena Cowan-Bailey

Photo | J. Fiereck Photography Orlena Cowan-Bailey


Human Resource Business Partner, MassMutual Financial Group

Age: 36

No. of years with current company: 1

Town where I live: East Hartford

Town where I work: Enfield and Springfield

College: Fairfield University

Highest degree: Bachelor’s degree in communications, HR certified

Who is your favorite superhero? Wonder Woman — As a mom, wife and HR guru I feel like a superhero a.k.a Wonder Woman every day, in every role.

Orlena Cowan-Bailey is a human resource business partner at MassMutual Financial Group providing strategic human resource consultation and leadership support across several business units.

She is also the chapter president for the Human Resource Association of Central CT (HRACC). As a volunteer leader she is tasked with leading a dedicated board of directors to promote and deliver HR excellence throughout Hartford and New Haven counties through professional development, scholarship, service and advocacy. Her leadership has driven sustainable operational results to enhance and evolve HRACC’s brand and footprint in the local HR community and beyond.

How are you involved in the community?

I’ve been involved in numerous community organizations over the years including HRACC, Urban League Greater Hartford, INROADS and BSL Educational Foundation, a nonprofit serving middle and high school aged youth of the Greater Hartford community. As a Hartford native, community involvement is a must.

What do you like to do outside of work?

I’m a culinary enthusiast! I love to cook and my husband loves to indulge in whatever I chef up so I often try new recipes and prepare my own signature dishes. Anything seafood is at the top of our taste-bud list. I love to watch Chopped, Guy Fieri and Beat Bobby Flay on Food Network. Work-life balance can be challenging so traveling and going on different adventures with my family and friends is a must.

Four reasons why you deserve to be a 40 Under Forty:

• Chapter president for the Human Resource Association of Central CT (HRACC) delivering and promoting HR excellence across Connecticut.

• Provided strategic HR leadership during the implementation of CTfastrak, a $567 million project and Connecticut’s first bus rapid transit system.

• Demonstrated passion and results in helping others (people and organizations) maximize their full potential.

• Re-emerging CT Realtor providing outstanding service and expertise to help clients fulfill their real estate needs and dreams.

Fun Fact

My alias name is #TheMomentMaker due to my creative and natural instinct for event planning and my ability to enhance milestone life experiences.

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