Collective Conversations: Aspireship Helps Professionals Pivot

Beth Cochran
Feb 25 · 4 min read

Have you ever felt stuck on your current career path? Well, you’re not alone. Data from Payscale shows that more than 80% of Americans feel trapped in their jobs. One of the biggest reasons for this is the struggle of switching roles after working in an industry for several years. That’s where Aspireship comes in.

Aspireship was founded by Corey Kossack, a member of the StartupAZ Collective 2020 growth cohort, to provide online training to those interested in a SaaS sales career, while also connecting them with a growing company looking to hire talent. In just two years, Aspireship has already had thousands of program graduates.

In the latest edition of Collective Conversations, Corey spoke with us about what inspired him to start Aspireship, the most rewarding part of the experience, and what the next steps are.

What was your background before you started Aspireship?

I’ve been an entrepreneur for most of my life. I previously founded a SaaS company called Frederick, which scaled to more than 10,000 businesses. I’ve been around the SaaS world for quite a long time, and I’m really passionate about the career development space.

How would you describe Aspireship to someone who has never heard of it before?

It’s a learning and talent platform for the SaaS industry, helping people who are looking to transition into the industry. For example, we help sales professionals who sold something else, like insurance, or people looking for their first sales job. We give them access to a free online training program to learn about what it takes to be a successful tech sales rep. If they’re able to pass the assessment and complete the program, we introduce them directly to hiring partners that we work with that are looking to find learners ready to hit the ground running.

Why did you start Aspireship?

After my last company was acquired, we became part of a large public entity with thousands of employees. Most people felt like they were completely stuck in their lane. Whether they were in marketing, customer support, or sales, they felt typecast. They couldn’t make any career pivots to different departments, because their specific niche was prohibiting them from really getting a shot at any new opportunities. Once you’re three-to-five years into your career, you’re on a certain track and it’s really hard to get off. At the same time, I saw how difficult it was inside a quickly growing company to hire, onboard, and retain talent, especially salespeople. So, I saw a really big gap between those two and wanted to solve the problem.

How much progress have you made since you started?

We’ve made a ton of progress. We have a team of 10, raised $3 million in VC funding, and have had thousands of people come through our program and graduate. We also have dozens of partners hiring our graduates.

What are some of the biggest challenges you’ve had to overcome?

We’re kind of like this weird blend of a SaaS company and a two-sided marketplace. The biggest thing is just balancing the supply and demand of the marketplace. We need to have the right volume of candidates for the right volume of companies at the right time. It’s a challenge but we’ve been able to balance it well so far.

What has been the best thing to happen to you since starting?

It’s seeing the outcomes for the individuals. We’ve helped people pivot their careers in record time, which is especially important considering the impact of the pandemic on a lot of different industries. We’ve been able to take people who had steady careers and a great career path who were suddenly laid off, retrain them very quickly, and have them land a job in a new industry and be very successful. Seeing that happen over and over again has been by far the most rewarding part of this process.

Why did you decide to join the StartupAZ Collective?

I love the idea of having a community of founders, who can help me and I can help them. I call it founder therapy, since you can meet one-on-one with different people in the group and vent about what we’re going through. I thought that was really valuable. I’ve been part of VC portfolios and their other founders I’m connected to, but specifically having something local and can have an impact on the startup scene in Arizona was attractive to me.

What has been your favorite part of the StartupAZ Collective?

It’s 100% the people. The group of founders that are involved is pretty high-caliber. They’re also really good people. Everybody wants to help each other. It’s a tight-knit group where everybody knows each other.

What are the next steps for Aspireship?

We’re growing at a pretty crazy clip right now, so our focus is on managing that. We’ll be growing the team and I’m sure we’ll raise more capital so we can expand the types of roles we can help people get into and the volume of companies we’re working with.

StartupAZ Foundation

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