CEO @ Aspireship | Helping people get hired in tech sales and customer success

I’ve dedicated my professional career to helping people who want to help themselves. Currently, I’m building Orchard, an AI career counseling platform for K-12 education, and Aspireship, an employee benefits platform for emerging companies that want to stay lean and profitable.

Corey Kossack

Riley Blaisdell 🦏

Welcome to my community. I call it the Cul-de-sac.Because instead of followers, I like to think of us as digital neighbors.A little about me.I used to think insurance was boring, like most of the world. And maybe that is why only 12–14% of people actually understand it, even though far more of us need to use it.As a parent of a child on the spectrum, navigating healthcare became very real, very fast.Before Titan was diagnosed, we took him to doctors and specialists. We were told he was regressing or that nothing was wrong.Then we met one specialist who, within the first five minutes, told us Titan was autistic and non-verbal.As a parent, it felt like my world collapsed. I cried at the thought of never hearing my son say, “I love you.”But that diagnosis gave us access to early intervention and a path forward.Fast forward eight years, and Titan is thriving.He is doing things they once said were impossible.Titan taught me that the word “impossible” is really “I’m possible.”And yes, he does say “I love you.”He is also a Play-Doh fanatic. We probably own more inventory than some stores.We also have a daughter named Mina Mae. It is often mispronounced. Think My-nah, not Me-nah.Her name was picked out before Titan’s, and they have a six-year, four-month, and twenty-seven-day age difference.Mina Mae is a collector of people. She loves our dog, Waffles, and is always willing to help. Even when she is in the way. Dishes and cooking sometimes take longer, but those moments matter.I met Megan while dressed as Cookie Monster at a Halloween going-away party for a mutual friend.She is the definition of resilience. After being laid off from Fred Meyer in 2020, she returned to school, earned her degree in Speech-Language Pathology, and was recently accepted into graduate school.As for me, I have been in sales my entire life.My first cold call was at sixteen. I have 7-figure deals under my belt, building them from scratch and maintaining relationships to help those clients grow their bottom line. Today, I help employers design benefit strategies that actually work for both the business and the people using them. I focus on understanding today’s challenges, planning for what is ahead, and solving them together.TogetherEveryoneAchievesMoreMy goal is to improve healthcare literacy and design plans that support real employee needs.Engage is the rage.Mahalo nui loa 🤙

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Corey Kossack

Riley Blaisdell 🦏

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