S12 E7: Your First Time Joining a Startup With No HR or Systems…What Could Go Wrong?! (with Christine Song)

Hebba Youssef
Hebba Youssef
June 1, 2026

There is a lot to say about joining a startup, and I’m saying that as somebody who has been a part of four of them.

Nothing prepares you for the first time, because you truly have no idea what you’re walking into!

Not even the offer letter or the job description paints the full picture, so Christine Song, founder of the 5 to 9 Society and former CPO at NYX, is here to give you her expertise.

We’re talking about walking into a company with no HR infrastructure, a CEO whose behavior made her want to run back to corporate, working 100 hours a week until her hair (literally) started falling out, and somehow still coming out the other side with more love for startups than ever. 

00:00:00 – Intro

00:02:01 – Something Christine Believed About Work That She Had to Unlearn

00:08:26 – What Stepping Into a Startup Role Felt like Vs The Expectation of It

00:21:01 – The Important Role of HR in Startups

00:35:18 – Picking Up on Signs of Burnout

00:40:40 – Startup Culture and Its Demands

00:49:10 – Creating a Life and Identity Outside of Work

00:55:11 – Christine’s Advice For Someone New to The Startup World

The Predictive Index behavioral assessment reveals how people work, think, and thrive—so teams can understand each other better and perform at their best.

Because when you truly understand your people, work just works.

Learn more: ⁠⁠⁠⁠⁠⁠trypi.com/ihateithere⁠⁠⁠⁠

If you love I Hate It Here, sign up to Hebba’s newsletter! It’s for jaded, overworked, and emotionally burnt-out HR/People Operations professionals needing a little inspiration. ⁠⁠https://workweek.com/discover-newsletters/i-hate-it-here-newsletter/⁠⁠

And if you love the podcast, be sure to check out⁠⁠ https://www.youtube.com/@ihateit-here⁠⁠ for even more exclusive insider content!

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Hebba Youssef
Hebba Youssef