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Allyssa Kaiser: “If you’re not rejected ten times a day, you’re not trying hard enough”

The pandemic has shed light on the significance of small businesses when it comes to our economy and the role they plan in the American dream. If I could inspire a movement, it would be to rally large organizations to help level-up small businesses — whether it be through exclusive collaborations, financial backing, charitable giving, or business […]

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The pandemic has shed light on the significance of small businesses when it comes to our economy and the role they plan in the American dream. If I could inspire a movement, it would be to rally large organizations to help level-up small businesses — whether it be through exclusive collaborations, financial backing, charitable giving, or business consultation, I would like to see Fortune 500 companies give back by lending a helping hand to small business owners. We have seen dozens of brands step up during the pandemic — notably, liquor brands in the restaurant industry — but I hope that this becomes a sustainable practice and not just a flash-in-the-pan PR stunt.


The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able to Pivot to A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Allyssa Kaiser.

Allyssa Kaiser is an accomplished marketer with nearly a decade of experience working with some of America’s best brands. Allyssa began her career agency-side servicing clients in financial services, technology, retail, and CPG, with a roster that includes Verizon, Visa, and Johnson & Johnson. She then made the transition from agency to brand-side and joined Bowlero Corporation, the largest owner and operator of bowling entertainment venues in the world, where she oversaw the company’s media investment across its portfolio of three brands and 300 locations. Today, Allyssa is the Director of Performance Marketing at women’s footwear brand Aerosoles.


Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in a small town called Big Lake, Minnesota (yes, that’s right — Midwestern kid in the house). Growing up, I was always eager to learn and had big dreams at a very young age. In my early formative years, I remember researching colleges and taking those assessment tests that are supposed to tell you what your future career would be. As a teenager, I discovered an affinity for the arts, so at 16, I applied to study at Perpich Center for Arts Education, a public arts high school just outside of Minneapolis. At Perpich, I found my passion for media, and this led to my decision to attend Syracuse University, where I studied Advertising at the S.I. Newhouse School of Public Communications.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“If you’re not rejected ten times a day, you’re not trying hard enough.” -Anthony Coleman

This quote has taken on a whole new meaning since the pandemic and its consequent implications on the job market. After being rejected by bots and automated systems a dozen times a day, I knew I had to make a change if I wanted to land that next great opportunity. Seeking out freelance gigs came with its own set of unique challenges, but I knew that if I continued to hustle, I would persevere.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Early on, Angela Lee Duckworth’s TED Talk Grit: The Power of Passion and Perseverance was hugely influential. In this video, Angela talks about the significance of motivation and how it can influence one’s success in life. Growing up, I never thought of myself as the smartest or most talented, but rather the student who most wanted to succeed. As a practitioner of marketing, grit has been critical to my personal journey and success in life to-date.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

I was fortunate to have been positioned for a year of growth and success at my prior employer. I had just been promoted to Director of Media, overseeing all paid media investments for the company, which spanned three core brands and 300 locations nationwide. The company had just agreed to sponsor my participation in a Harvard Business School course focused on digital marketing, and I was well on my way to establishing myself as a leader and marketing expert within the company. I had just hit a huge career milestone.

What did you do to pivot as a result of the Pandemic?

As a result of national legislation and city ordinances, which forced the closure of all locations, my employer decided to lay off and furlough a significant percentage of its staff at both the corporate and field level, which directly impacted my newly attained position. After struggling to find full-time opportunities in the then-turbulent job market, layoffs and furloughs abound, I decided to pursue freelancing and began seeking out contract-based work. In August, Aerosoles recruited me as a consultant for a two-month preliminary contract.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

The industry shift to freelancing is nothing new. A 2017 study by Upwork found that 36% of the workforce (57.3 million) were freelancers. Then, freelancers contributed approximately 1.4 trillion dollars annually to the economy. 2020 has further accelerated this workforce shift. Like many things, the pandemic rocked recruiting and talent initiatives for companies large and small, many of which experienced hiring freezes, furloughs, and layoffs. For a few months, it seemed that anyone who was on the job market was facing a road of hardship. However, when cities began to loosen their restrictions, many decision-makers were met with the challenge of staffing up quickly while mitigating risk and managing to plan.

I noticed the shift to contractual talent earlier this summer when I faced a challenging job market. Although many companies had listed full-time roles that matched my skills and experience, the reality was that the majority of hiring managers I spoke with ultimately did not have the authority to bring on full-time talent. As the summer went on, I noticed the same job listings being posted again and again as contract roles — and a flurry of new contract roles had also hit the job boards. It was clear at that point what my next move would be.

How are things going with this new initiative?

After completing my two-month contract, I accepted a full-time position with Aerosoles as their Director of Performance Marketing. However, since announcing this career pivot, I have been approached by several potential clients about freelance work in the social and digital marketing space. I am now privileged to choose my career path forward, whether it be as a full-time employee or freelancer.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

First off, major shout-out to my manager at Aerosoles, Jenny Dwork, who hired me during a tough time in the industry and has been my cheerleader since Day 1. Under her leadership, we have had several big wins. I am looking forward to contributing to our recent success as a new full-time member of the team. I would also like to thank Eric Schoenberg, a friend and industry connection who continues to act as an ally for many in the advertising industry and has been a long-time supporter.

Can you share the most interesting story that happened to you since you started in this new direction?

Since announcing this pivot, I have gotten a lot of kudos from friends and industry leaders for having been brave enough to go out on my own and essentially start my own business in the middle of a crisis, which was something I had not expected. It certainly takes courage to go the route of freelancing, but the pandemic gave me the window of opportunity. I honestly don’t know if I would have taken this step had there not been the pandemic.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

I spend the majority of my days managing and optimizing advertising campaigns across channels like Facebook and Instagram, so escaping the news cycle is virtually impossible for me. However, I’ve made an overt effort to follow people and conversations that inspire and uplift. ‘Doomscrolling’ negatively impacts mental health and despite our best efforts, it presents itself as a constant risk when we spend so much time on our phones.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

The pandemic has shed light on the significance of small businesses when it comes to our economy and the role they plan in the American dream. If I could inspire a movement, it would be to rally large organizations to help level-up small businesses — whether it be through exclusive collaborations, financial backing, charitable giving, or business consultation, I would like to see Fortune 500 companies give back by lending a helping hand to small business owners. We have seen dozens of brands step up during the pandemic — notably, liquor brands in the restaurant industry — but I hope that this becomes a sustainable practice and not just a flash-in-the-pan PR stunt.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

Bethenny Frankel is an inspiration — both her ambition and resilience. I’m also admittedly a huge fan of the Real Housewives franchise. Enjoying lunch (and a few Skinnygirl margaritas) with her would be a dream come true.

How can our readers follow you online?

For professional ramblings, real-time Minnesota Vikings game updates, and my obsession with the Drybar, follow me at @AllyssaKaiser. For business and/or collaboration opportunities, you can send me a connection request on LinkedIn.

Thank you so much for sharing these important insights. We wish you continued success and good health!

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