I had the privilege to photograph Jacqueline Rinehart, JD MBA , a fractional Chief Artificial Intelligence Officer. She shared some of her journey.
“I work in AI & digital technology for the betterment of humankind, often leading in first-ever roles that drive innovation. I provide vision & structure that help people make change happen. I have been honored to do this for 23+ years in start-ups, FinTech, Fortune 50 & Big 4.
Innovation is in my DNA.
While serving as a lawyer for the NYPD, I worked with the police to root out crime & draw in economic investment in Harlem, Washington Heights & the Lower East Side. I led groundbreaking approaches coordinating multi-agencies for raids in the middle of the night to drive transformation.
I’ll never forget one night in Harlem with an officer assigned to me, we went into a crack den the police thought was a deserted building. Suddenly guns were shooting. Someone grabbed me & threw me into a car. It was like a scene from a movie. Yet, I was fearless in my desire to better the neighborhood. I felt I had the best job, but something more was calling me.
Through exposure to the NYC Economic Development Department, I decided to go to Yale to explore innovative public finance. I discovered & focused on emerging technologies with organizational transformation.
I made my business career in San Francisco. I went for an interview but stayed for a job created for me in finance & tech transformation. Whatever the latest technology was, I learned it naturally & incorporated it into my work. I taught myself everything with hands-on programmatic approaches that proved successful.
Eventually, I needed to step away from tech & urban living, so I moved to Hawaii. I wanted the journey & strength that came from reconnecting with myself by being closer to nature & living in the culture of Aloha.
Armed with certainty, I went to the jungles of Kauai working with a grass roots innovator who had built an operating model for sustainable agricultural. I was going to be the COO, but my executive leadership reignited a desire for big transformation & huge impact in evolving AI. New York City was calling.”
My advice:
Be confident in the choices you make for yourself; your journey is yours & yours only.
My discovery:
No matter where I went or how far, I returned to New York City where it all began!
With this discovery, I wanted a headshot encompassing all of me.
While known for my transformation & innovation superpowers, I wanted both my executive presence & passionate persona to shine through. I wanted the photo to embody my dynamism that promotes new ideas, my inclusive aloha spirit that shepherds innovation, & contagious leadership confidence, all brought together by my unique career journey.
Through Chief, I met Alissa. Her hair & makeup artist, Lisa made me look like an executive feminine powerhouse. Alissa brought out the qualities that I wanted to reveal in photos & we all had great fun!”
About Alissa
Alissa Randall is a portrait photographer based in New Jersey and New York City, known for creating images that feel both elevated and deeply personal. While professional headshots remain a cornerstone of her work, her photography has grown to include personal branding, women’s empowerment, family connection sessions, and expressive portraits of dogs and the people who love them.
Her approach blends editorial artistry with empathy and guidance, helping people feel comfortable enough to be fully seen in front of the camera. Whether photographing an executive, an entrepreneur, a family, or a beloved dog, Alissa creates photographs that reflect more than appearance. They reflect presence, personality, connection, and story.
Alissa photographs in NJ, NYC, and on location beyond the tri-state area. Explore more of her work on the homepage and discover stories behind the images on the blog.