Jordan Cutler

Tell me about yourself and your journey into big tech.

When I first started thinking about getting into tech, I thought I needed a computer science degree. So I studied CS at Lehigh. I also thought the best way into big tech was through internships. I figured if I could get a big name on my resume early, that would give me a good jumping-off point for full-time roles later. And internships seemed like the easiest path to conversion.

During my sophomore year, I was deep into LeetCode prep. I applied to pretty much every big tech company - and Twitter ended up being one of the few that responded. I studied really hard. I used to be addicted to video games, but at that point, I basically swapped that addiction for LeetCode, which ended up helping me pass the interview.

The internship went well and I got a return offer. But when I went back to Twitter for my second internship, it didn’t go as well. Ultimately, I wasn’t converted so I had to apply to a bunch of other places.

Luckily, having Twitter on my resume helped me get interviews - even though I was still getting rejections. Eventually I found a company I really liked called Gusto which is where I ultimately started my career journey. It was a bit smaller than Twitter, but I really liked it and I learned a ton.

After that, I decided to go to an even smaller startup called Qualified. I thought I’d be able to make a bigger impact and learn more doing things from the ground up. But I realized I didn’t like the lack of process that comes with early-stage startups as much so that led me to Pinterest.

Through my content creation, I had some connections there, and I got a referral. I studied hard for the interviews and landed the role about a year ago - and I’ve really enjoyed it so far.

I wasn’t expecting you to say your LinkedIn content helped you get a referral. Would you recommend other engineers start posting on LinkedIn too?

Yeah, it definitely helped me get referrals at a bunch of big tech companies. 

That said, I don’t think you should do content creation just for the sake of it. If you’re not genuinely interested, it probably won’t stick. I think the better approach is to start with a goal and work backwards. For example, I like learning new things - but I learn better when I teach them. That’s why I enjoy content creation. It helps me process what I’m learning.

Like recently, I was trying to wrap my head around this new AI concept called the Model Context Protocol (MCP). I decided to spend a day learning it - and the best way for me to do that was by writing an article. If I could explain it well, I knew I understood it to the level I wanted to.

In your current role, what does a typical day look like and what are your main job responsibilities?

The thing I love about my job is that no two days look the same. I’ve worked on everything from performance audits to redefining how we handle navigation across the app. There’s a ton of different areas you can dive into.

For example, this week, I organized a learning hour for our org and brought in a guest speaker. Last week, we had an on-site where I hosted roundtables across teams on tough topics. So a lot of my job goes beyond just writing code.

Of course, there’s coding too. But I also spend time writing documentation, creating design docs before we start projects, and mentoring. Every week I meet with mentees to make sure they’re supported and have what they need. If I can connect them to resources or unblock them in any way, I do.

It’s a mix of technical work, team support, and culture building. I really like that balance.

What advice do you have for others who want to break into big tech or do what you do?

Start with the goal and work backwards.

If your goal is to get into big tech, your first step is getting your foot in the door. One of the fastest ways to do that is through a referral. So figure out how to make that happen.

A lot of people say “just reach out,” but I think it’s important to go deeper and talk about how to do that well. Everyone’s different, but I can share what’s worked for me.

First, don’t send a huge wall of text that’s hard to read and only focuses on you. Try to put yourself in the shoes of the person you’re messaging. They’re probably busy, so you want to be respectful of their time and get straight to the point.

Personally, I’d lead with the ask. Something like:

“Hey, I know we haven’t met and I don’t expect anything from you - but if I can make it worth your time, I’d love to try. I’m interested in [insert role], here’s my resume [attach or link], and here’s all the info you’d need if you’re open to submitting a referral (email, phone, etc.). Totally understand either way - thanks for reading.”

Make it easy. The more straightforward and low-effort it is for them to help you, the better.

And before you reach out, make sure your resume is strong. I see a lot of people spending hours on LeetCode and interview prep - but none of that matters if you can’t get the interview. Your resume has to be something someone feels confident putting their name behind.

You can follow Jordan on LinkedIn and subscribe to his newsletter, High Growth Engineer where he shares concrete, actionable advice on everything from job search strategies to growing faster in your career. 

I especially love this article: Navigating Job Searches During Layoff Periods: Advice for Engineers and this link to helpful, free resources. 

An Update on Coffee Chats

After 19 interviews, I’ve made the tough decision to wrap up Coffee Chats.

When I first launched this newsletter, I wanted to create space for real, unfiltered career stories - the kind we don’t always see on LinkedIn. Stories about layoffs, pivots, reinventions, and the messy middle of figuring things out.

Thanks to all of you, it became more than I imagined. I’m incredibly grateful for the conversations it sparked and the people it brought into my orbit. I’ve learned so much from these conversations, and I hope you did too.

Behind the scenes, I’ve been working on something I’m really excited about, and in order to give it the space it deserves, I’ve had to make some tough decisions about where my energy goes.

If you’ve been a reader, shared an interview, or reached out after an issue landed in your inbox - thank you. This project will always hold a special place for me - and who knows, maybe it’ll return in a different form someday.

And while this chapter is ending, there’s more to come. I’ll be sharing what I’m building next soon - stay tuned on LinkedIn.

With gratitude,

Brenna

Other ways I can help you

Download my personal resume template: It has helped me land interviews at companies like Meta, Google, TikTok, Salesforce, and Uber.