In conversation with… Kylie Robison of Fortune

If you follow technology, you’ve likely come across an article from Kylie Robison. She’s on the front lines of breaking tech news at Fortune, covering giants like Facebook, Amazon, and X. Previously, she worked at Business Insider where she reported on eye-opening topics like allegations of pay inequality at Peloton (more on that below) and the implosion of Stripe-backed startup, Fast.  

I recently caught up with Kylie to chat about career challenges, her favorite story she’s ever written, what her career path might’ve looked like had she not gone into journalism, and more (including the best place to grab a panini in San Francisco).

How do you begin your workday?

I wake up with my cat and give him a cuddle first and foremost. Then I make an espresso and do a proper doomscroll of Slack, Twitter, and Techmeme. If I’m going to the office, I’m chugging two espressos and doing my scroll on the bus.

What is the most challenging part of your job?

Something I call brute forcing cold outreach. Sometimes, in order to get a story, you have to reach out to a hundred (or several hundred) people at a company. Most will ignore you, some will respond something snarky, and very few will be up to chat. It’s not my favorite way to source but it can certainly be worthwhile.

What’s one thing people would be surprised to know about you?

I have a bunch of younger siblings, the youngest just turned 3 and the oldest just turned 18. I really enjoy watching them all grow up and of course, being their cool eldest sister. We’ll see how long it takes them to realize I’m not that cool, though.

Of all the stories you’ve written, which one is your favorite and why?

It’s very hard to pick just one! Each of my favorites rank highly for me not because they got a lot of attention, but because I learned a lot in the course of reporting them. I’d say my most formative story to date was when I was a fledgling reporter at Business Insider: Black employees at Peloton are hammering the company with questions about being paid less. It was my most ambitious story to date, and it was on a sensitive topic requiring countless hours of phone calls with people in dismal situations. However, this feature catapulted me into the Peloton beat until activist investors cited my reporting for a reason Peloton’s CEO needs to step down, in which he did. I learned a ton, and I’m a better reporter because of it.

What career would you have/want if you weren’t a journalist?

I studied business management information systems so I was going to work in developer relations (devrel) or network engineering before I accidentally became a journalist. Realistically, that’s what I’d be. In a perfect and just world, I’d make tech money working in the service industry. I’ve had soooo many part-time service jobs, and still fantasize about working a barista gig on the weekends.

Favorite place in San Francisco to grab a coffee or a bite?

Café du Soleil in Lower Haight for coffee and cross the street to Tarragon Café for a panini.

You can follow Kylie on X at @kyliebytes and LinkedIn