Re-Imagineer: Alissa Randall

1) You had a successful career as a marketing executive, including CMO for Step Up for Students, a large educational choice nonprofit. You then took a Reimagination turn to become a professional headshot and brand photographer. Tell us about that decision and what led you to this pivot?

I was a CMO and had worked in marketing for most of my adult life. Suddenly I was given what turned out to be a wonderful gift – my position was eliminated. That same afternoon I started my headshot photography business.

I’ve always loved photography. It’s where I felt at home, but I didn’t know anything about headshot photography until my brother David, also a photographer, mentioned it to me. I was a natural light and street photographer and didn’t know how to shoot with lights. I’d recently bought some – they were all set up, but I wasn’t using them. I called B&H Photo and they put me in touch with their amazing rep. I said: “I lost my job this morning and I’m starting my headshot business. Can you come over and teach me how to use the lights?” He came over a few days later. I remember him saying, “I don’t know why I said yes to you…” I’m so happy that he did.

I realized at that moment that life happens. It can be scary, but also a fantastic adventure. When you’re supposed to be somewhere doing something, things align. I’m forever grateful to Cliff Hausner at Profoto, you changed my life. Thank you so much.

2)Your company is called All About Headshots. It began May 19, 2022. Give us some insights on the company, your success, and what’s next?

That’s such a great question. I love photographing headshots and connecting with my clients – I see myself doing it for the next 20 years.

My favorite part of the process is helping people see themselves for the first time in their pictures. Showing them how unique and beautiful they are, capturing their essence. I always shoot with my camera plugged into a monitor and they can see exactly how they look immediately, right there in the studio.

I do a lot of coaching with clients, including facial expressions. Based on what they like in the shots we’ve done; I help adjust their stance and expression and they start to realize that they are going to love their headshots.

As for what’s next I have a few ideas up my sleeve… including dog photography. One thing I know for sure, it’s going to be an exciting time ahead.

3) What advice would you give someone who wants to make the kind of move that you did from your CMO role to becoming an entrepreneur in a creative endeavor like you did?

Go for it. Be bold. ROAR into it! I know that leaving a corporate position and starting on your own is scary, but it’s so empowering. It feels like you’re spreading your wings and soaring. Every day is an opportunity to stretch and grow and learn. 

When I was thinking about starting All About Headshots I chatted with a coach, Marissa Fernandez. I told her I wanted to be that 70-year-old looking back on an incredible second career. She asked me what words I would use to describe the older me. I said: moxie, creative, energetic, sophisticated, smart with business, empathetic, strong and inspiring. She simply said, you’re all those words now. I took that and ran with it. Thank you, Marissa!

Above all, as an entrepreneur you can serve your clients in a way that aligns with what they need and would like, while growing and evolving yourself.

How do people learn more about All About Headshots?

Mostly referral.

My website is, and you can see lots of examples of my work on Instagram @allaboutheadshots.

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