What does it take to go from copywriter to executive at a YC-backed company? For Jess, it started with doing it scared.

Jess spent over a decade as a creative at top agencies, writing scripts for Snap, Crackle and Pop, tweeting as Tony the Tiger, and leading campaigns for brands like Kellogg’s and McDonald’s. Then she made a pivot that terrified her — leaving advertising for B2B tech — and had to learn an entirely new way of thinking, working, and selling ideas.

In this conversation, we talk about what it actually looks like to collaborate across teams when your work depends on other people to distribute it, how to build confidence through repetition (not before it), and why the best marketing comes from understanding everyone else’s job as well as your own.

Connect with Jess Cook: LinkedIn Connect with Laura Colagrande: LinkedIn

Timestamps:

* 00:00 Intro

* 00:29 The research report “oh s**t” moment

* 04:22 How to get people to care about your work

* 07:47 From Tony the Tiger to B2B marketing

* 12:03 Learning to tie creativity to business impact

* 14:52 The “what happens if...” mindset

* 20:10 Finding the company that celebrates creative thinking

* 26:07 Why creative people will win the next wave of marketing

* 28:51 The Happy Meal box lesson (understand your job and everyone else’s)

* 33:48 How to talk about collaboration in job interviews

* 37:43 “Control the s**t out of what you can control”

* 41:15 Influence Shout Out and Closing

One thing you’ll take away:

Collaboration isn’t a soft skill — it’s the skill. The people who move up fastest are the ones who understand not just their role, but everyone else’s.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit softsides.substack.com