The Great Re-port on Work

Cassandra’s latest report is here

As a generation, Gen Z has been labeled as coddled and unwilling—or unable—to work hard. However, these accusations so completely miss the mark as they, in fact, are one of the most accomplished and capable generations, but also one of the most pragmatic. So, it’s of no surprise that Gen Z, who will make up 30% of the U.S. workforce by 2030, are not falling into the “dream job” trope, which, let's be honest, isn’t the be-all and end-all in today’s unstable landscape.


In this month's The Great Re-port on Work, available exclusively to subscribers, Cassandra set some boundaries, and went hustling on the side to uncover how Gen Z strives for emotional, professional, and financial success while not defining themselves by their work. Here, we’re offering a sneak peek of the report by spotlighting three brands changing how Gen Zs support their entry into the workforce.


Jipe is a new job search app designed exclusively to match teens and young adults with entry-level jobs.

The platform works a lot like dating apps: users simply swipe to apply for jobs, a process the app makes quick and easy for both the applicants and the employers.

Part of Jipe’s value proposition is that users don’t need a resume to get started, instead helping build work profiles with all users, like a mini resume that’s stored in the app and submitted with every application. The app helps users write a bio, identify top skills, and be ready to start applying in about five minutes.

— Estrella, 21, CA (Cassandra Collective)


Huru: Launched in 2022, Huru serves as the ultimate job interview coaching app where users can prepare like a pro with its over 20,000 interview questions from more than 300 professions, covering nearly every career occupation category in the job market, varying from entry-level to executive positions and all in between.

Huru takes technology a step further by analyzing answers with Artificial Intelligence (AI), assessing job hunters’ chances of getting hired, giving feedback on the answers, and providing interview tips and insights.


Pineapple: Lauded as “LinkedIn for Gen Z,” the recently launched app aims to reshape professional networking for Gen Z.

The idea behind Pineapple is to give young professionals a way to network with others through a visual story profile that’s kind of like a digital portfolio.

The professional network is the brainchild of Pineapple’s 22-year-old co-founder and CEO David Diamond, who says that one of the main focuses of Pineapple is communities, which aim to help users find other people who are passionate about the same thing as them. There are specific communities for various topics, from VCs to marketers to designers.