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2022 Connect x BizBash 40 Under 40: Jessica Boskoff

Jessica Boskoff, 39, is the founder and CEO of Twenty Three Layers.

Jessica Boskoff

Jessica Boskoff, 39, is the founder and CEO of Twenty Three Layers. She's based in New York.

What I do: 
Being a founder, I wear endless hats, and there’s no job I won’t or have not done. When on-site it’s anything from opening boxes to show-calling. It’s incredibly important to know every facet of the job, so when you are assigning roles and responsibilities to others, there’s a better understanding of what it takes.

When not on-site, most of my time is taken up by pre-production and design (as I’m also the creative director), business development, forecasting, fostering relationships, growing the team and the culture, working on marketing efforts and special projects and everything in between.

Why I love my job:
I’ve always said that most people who work in event planning and production must love their jobs, as it’s a super intense and stressful field to work in. Why do I love what I do? The gratification that comes from creating something out of nothing—and the human connection that events foster. I love the process and the journey I’ve been through, as I’ve built something I can be proud of. But beyond that, I love all the possibilities and opportunities that come along with it.   

My career journey: 
I worked as a media buyer for three years before realizing how much I wanted to get into the world of hospitality, so I was introduced to Soho House. Long story short, while working my nine to five in media, I decided to work from 5 p.m.- 2 a.m. every night at Soho House for six months, learning the ropes as an intern, shadowing whoever I could. I was in the kitchen with the chefs, at the front desk, in housekeeping taking out the garbage, overnight with accounting, closing the restaurant and bar with the floor managers—you name it, I did it.

I moved up the ranks quickly and landed a role as the events and F&B manager, and after a few years at Soho House New York, my experiences led me to a start-up called Four Hundred, a lifestyle concierge and travel firm, where I held the position of vice president for five years. Within that last year came the inception of Twenty Three Layers—and here I am over a decade later.

My greatest career accomplishment:
Within my 16-year run in hospitality and events, starting Twenty Three Layers is my greatest career accomplishment—all while eight months pregnant with my first child. The second proudest achievement would have to be when I hired my first employee. It may not sound like a typical accomplishment most would acknowledge, but it was a total game-changer and created so much opportunity for the company—not to mention, it was the catalyst to a handful of awards we’ve won for our work in events.

How I helped my organization during COVID:
COVID was an extraordinary time, and there wasn’t any kind of rule book to follow. Keeping the team together for as long as I could was important to me. Then, during the furlough period, I had more time to re-evaluate. Since events were still restricted, I shifted my focus to other opportunities that felt organic and allowed me to build more "layers" of what we can provide to clients—including brand strategy consulting.  

The time I averted a complete event disaster:
I can remember one year at the Cannes Lions Festival, we were producing a series of weeklong events for our client—and just a couple of hours before the main event we realized that their team had never shut down the guest list. The capacity of the yacht was about 60 people due to weight constraints, and the guest list was up to 1,500 people.

So, we went to the yachts on the right and left side of ours and convinced them to allow us to adjoin all three together to create one monster event (with a special performance). We quickly had AV, security and F&B looped throughout the three yachts and formed a single file line that moved guests strategically into each of the three spaces. It was a totally crazy experience, but we made it through! 

My most memorable event experience in the past year:
A memorable experience I’ve had in the past year comes from one of our social events. Fourteen couples, who have been best friends since grade school in Venezuela, traveled from all over to a three-day retreat at Paws Up in Montana. After what the world had just gone through, bringing people together, creating special experiences for them and seeing the love they had for each other—well, it was a beautiful experience and a reminder of how impactful what we do can be for others. 

Best advice I’ve ever received:
A close friend and founder once said that everyone is replaceable, including himself. As a founder myself, that advice has humbled me, and in challenging times, it has been a comforting reminder that the show must go on. It’s probably one of the simplest, yet most impactful things I’ve learned in business. 

Impressive stats I’m responsible for:
The company went from focusing on mostly social events a decade ago to then working across multiple verticals within the corporate space: advertising, technology, beauty, CPG and retail, health and wellness, publishing and telecom. Additionally, I’ve been able to increase the number of revenue streams by three-fold in the last two years through market expansion and strategic partnerships.

What’s next?
It’s wonderful to get back to our tentpole events, but I’ve been working on some exciting stuff like retail store design and development, brand-focused pop-up experiences, and assisting D to C brands like Waterdrop as we conceptualize their customer journey and expansion into the U.S. market. Being part of a brand launch team has been amazing and something we will continue to explore.

Plus, there is a new and exciting project in the pipeline that’s product-based—a tableware and textiles line. Yep, you heard it here first!  

What I do outside of work: 
A few things I really enjoy doing in my free time would be interior design, traveling and reading books in my new home library. They all contribute to feeling alive, inspired and recharged.

Connect with Boskoff on LinkedIn and Instagram.


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“Connect x BizBash 40 Under 40” is sponsored by VDA, an experiential marketing and event design agency based in Massachusetts that specializes in custom live, virtual and hybrid experiences.