Interview Mastery: Brad Garropy's Big Tech Job Search Guide
Jul 18, 2025
In this episode of Guidance Counselor 2.0, host Taylor Desseyn spoke with Brad Garropy, Senior Frontend Engineer at Cloudflare, about his recent journey through multiple job searches at major tech companies. Having successfully navigated roles at Atlassian, Stripe, and now Cloudflare, Brad shares tactical advice on interview preparation, company culture assessment, and the realities of job searching in today's tech market.
The Reality of Job Searching: Two Different Approaches
Brad's experience over the past year has given him unique insights into the job search process. He identifies two distinct types of job hunts that professionals encounter:
"There's one where you're casually looking, maybe feeling things out. And then there's another one where you are going hard, you're focused, you're practicing, you're driving towards an end result."
His preference leans toward the focused approach, despite the pressure it creates: "I like the focused ones, to be honest. There's pressure. But at the same time, when your head is so in the game, every interview is just another interview. You're ready for it. You've prepped for it. You've studied for it."
This focused mindset transforms the interview experience from a stressful unknown into a practiced routine. When properly prepared, technical challenges become manageable: "Use a set, use a map, use a for loop. You're good to go."
Company Culture Assessment: The Three-Week Rule
One of Brad's most valuable insights concerns how quickly you can assess company culture after starting a new role. His experience across multiple organizations has taught him that the truth about workplace dynamics becomes apparent relatively quickly.
"I feel like within three weeks, you get out of your initial phase, whatever, you're getting mentored or you're getting run through training programs. You actually start working with a team. How people interact with you when you're asking questions early on will set the tone for the entire relationship."
The red flags become apparent when companies have unrealistic expectations: "If they say, no, you're a senior, you should know everything. Red flag. There's some companies who are like we want to hire amazing engineers, sit you down and whip you to produce features top to bottom."
Brad has also noticed geographic patterns in company expectations: "San Francisco companies tend to be a little bit more like everybody's an A plus engineer and we fully expect that. Asking for help is like, bro, you should know that kind of stuff. But these companies have huge code bases at the end of the day and it's complicated."
Strategic Interview Questions for Culture Assessment
Despite the difficulty of fully assessing company culture during interviews, Brad has developed a strategic approach to gathering cultural intelligence through specific questions focused on collaboration and team dynamics:
Team Collaboration Questions:
How do you plan work?
How do you track your work?
How do you divvy up your work?
How do you determine success?
Is success measured individually or as a team delivering a feature?
How do you do stack ranking?
What do performance reviews look like?
These questions reveal whether a company operates as "an every man for himself type of company" or "a we win as a team type of company" - a distinction Brad considers crucial for workplace satisfaction.
He also emphasizes the value of speaking with actual team members: "If you can get your interviews with people on the team that you're going to work with, you get a much better understanding of just the personalities you'll be dealing with."
Technical Interview Preparation: The LeetCode Reality
Brad's approach to technical interview preparation evolved significantly during his recent job searches. Initially resistant to LeetCode practice, he eventually embraced it and found it transformational for his interview performance.
"I was the kind of guy who like didn't want to practice LeetCode and stuff. And this time around, I was like, I'm going to do it. And I just, my brain just started going into that mode. And as soon as you can think that way, they're not that hard."
His perspective on technical interviews is pragmatic rather than academic: "Companies nowadays are just seeing if you can get through a thinking exercise. You don't have to know depth first and breadth first search on a tree and how to implement that. You might get a rogue company that asks something like that, but then my take is like, meh, then they're only going to get a certain type of engineering."
The key insight is that preparation enables confidence: "Once you get your brain moving in what they want to see, they want you to talk out the solution. They want you to use kind of basic data structures that are meant for the job. Sets and maps are the most common ones."
The Art of Talking While Coding
Perhaps Brad's most unique advice concerns developing the ability to verbalize thought processes while coding - a skill that significantly differentiates candidates during technical interviews.
"I think my biggest thing is just being able to talk and code at the same time. Turn on your camera and record on your computer and then delete it when it's done or watch yourself and then delete it when it's done."
This practice serves multiple purposes beyond interview preparation: "You realize a lot of ticks you have. Why do I open my mouth like that when I code? Get comfortable thinking out loud, get comfortable thinking through something and not feeling so much pressure."
Brad took this practice public by streaming on Twitch while solving LeetCode problems, creating both accountability and real interview conditions. He also maintains a private GitHub repository of interview questions and solutions: "Every single time I take those questions and I like finalize that solution and post it up to my GitHub privately to not break any NDAs."
Systematic Job Search Organization
Brad's job search process is highly organized and data-driven, beginning with front-loading applications and comprehensive tracking systems.
Application Phase:
30-40 applications over 3 months typically
Comprehensive spreadsheet tracking application dates, contacts, companies, and positions
Notion database linking to detailed interview information
Interview Preparation:
LinkedIn and GitHub research for each interviewer
Finding common ground for relationship building: "I try to find something in common with them so that if you're there, you're like, oh, shit, you went to UT, you know, hook and horns, whatever, like anything to break the ice."
Study Phase:
LeetCode practice for technical problem-solving
React fundamentals review
Listening to technical podcasts for current knowledge
Building practice applications
This systematic approach ensures consistent performance across multiple interview processes while maintaining detailed records for future reference.
The Network Effect: Information Over Influence
Contrary to common advice about networking for job acquisition, Brad's experience suggests that online presence and content creation don't directly generate job offers, but they do provide valuable intelligence.
"I would have always loved to have said my GitHub profile and my Twitter and my podcast and my YouTube channel. Nobody gives a crap. It's great. It builds your network for people to reach out to for positions."
The real value comes from access to insider information: "I got to talk to people who worked at Cloudflare that knew what happened on the inside. And I could be like, is this a good place to work? And they can tell you yes. So it's less of a black box."
Brad emphasizes that networking provides crucial cultural intelligence that formal interviews cannot: "I think it plays a part in getting more information, like inside information about a company, if it's a good place to work. They could confirm or deny that, giving you the information the interviewers won't tell you."
However, he warns about potential risks: he once had an offer pulled for reaching out to employees at a small startup, despite being encouraged to do so during the interview process.
Resume Strategy: Simplicity and Keywords
Brad's resume approach focuses on clarity and searchability rather than customization or cover letters:
"I never customize my resume and I never write a cover letter. I do have a section of my resume where it's kind of like a word dump but it's like tools and technologies that I know and it's this whole section of just like stuff that I've worked with so people ever need to filter on keywords it's kind of there."
His resume structure includes:
One-sentence objective stating preferences (remote/hybrid, front-end focus, leadership interests)
Tools and technologies keyword section
Work experience
Side projects
This approach prioritizes getting through initial screening filters while maintaining authenticity in the application process.
Application Strategy: Direct Over Easy
Brad strongly advocates for applying directly through company websites rather than using LinkedIn's Easy Apply feature:
"Do not ever apply on LinkedIn. Apply directly on the job website. You're gonna have a much higher chance of getting called. In LinkedIn, everybody can press one button, easy apply, everybody does it. Most companies stay away from that."
This advice aligns with feedback from engineering leaders who report focusing primarily on their career pages due to the volume and quality issues with platform-based applications.
AI Integration in Interviews
Brad's approach to AI tools during interviews demonstrates professional acknowledgment while maintaining interview integrity:
"I'll leave GitHub Copilot autocompletions turned on, and I won't use the chat. And I'll just kind of say, I'm coding along, and I'll go, oh, hey, thanks, GitHub Copilot. And I'll go, oh, by the way, is it cool if I leave my tools on or what do you want me to do? But I kind of acknowledge that I am skilled in using these tools, but also I respect the process."
This approach normalizes AI tool usage while demonstrating professional judgment about appropriate usage contexts.
Career Mobility: The New Normal
Brad's experience reflects broader changes in tech career expectations. Having moved between multiple prestigious companies in a short timeframe, he encountered minimal resistance:
"In most cases, nobody ever even said anything. People go, yeah, people move in tech. There was a lot of layoffs lately. They just kind of assume and then they go, it's fine. This guy's had a history of pretty good jobs for three to seven years. There's a blip. Who cares?"
This represents a significant shift from earlier career norms where frequent job changes raised red flags. Companies are adapting their compensation structures to match new mobility expectations, with some organizations front-loading equity vesting to retain talent for shorter periods.
Company Selection Criteria
Brad's experience across different company sizes has refined his preferences toward smaller, more innovative organizations:
"I've had probably five different companies I've worked for over the years, all have been fairly big companies and every step I've taken has gone to a smaller and smaller company."
His attraction to Cloudflare stems from both its size and innovation pace: "I feel like every day we're shipping some stuff that's like a big deal. Really cool big things, the company's shipping. And so you might have a longer tail at a company like that that's fun to work for, that's innovating."
This suggests that company trajectory and innovation potential may be more important for retention than traditional factors like size or stability.
First Career Transition Advice
Reflecting on his career journey, Brad identifies staying too long at his first job as a key mistake:
"Don't stay at your first job too long. Like it's easy to get comfortable when you're finding your partner, getting married, going through all stages of life. A lot of things happen right after college and I stayed at that first job for probably too long."
His advice emphasizes proactive career development: "Get involved in the tech community. There's a lot of stuff going on. And it'll excite you and you'll want to go explore different companies and touch different technologies."
Practical Takeaways for Job Seekers
Brad's experience provides several actionable insights for professionals navigating tech job searches:
Preparation Strategy:
Practice coding while verbalizing thought processes
Maintain organized tracking systems for applications and interviews
Research individual interviewers for relationship-building opportunities
Focus on fundamental skills rather than advanced algorithms
Application Approach:
Apply directly through company websites
Include comprehensive keyword sections in resumes
Avoid over-customization in favor of consistent quality
Culture Assessment:
Ask specific questions about team collaboration and success metrics
Leverage network connections for insider perspectives
Pay attention to early interactions as cultural indicators
Technical Skills:
Practice with LeetCode but focus on fundamental problem-solving
Develop comfort with AI tools while maintaining professional judgment
Review framework fundamentals regularly
Long-term Career Strategy
Brad's journey illustrates the importance of continuous learning and adaptation in tech careers. His willingness to embrace previously avoided practices (like LeetCode) when they proved necessary demonstrates the flexibility required for career advancement.
His preference for companies that balance innovation with stability suggests that professionals should evaluate opportunities based on learning potential and growth trajectory rather than just compensation or prestige.
Conclusion
Brad Garropy's experience navigating multiple job searches at top-tier tech companies provides a masterclass in systematic interview preparation and company evaluation. His emphasis on practical preparation, systematic organization, and honest culture assessment offers a roadmap for professionals seeking to advance their careers in competitive markets.
The key insight from Brad's journey is that success in tech job searches combines thorough preparation with authentic presentation. By developing both technical skills and communication abilities while maintaining organized systems for tracking and evaluation, professionals can navigate even competitive markets successfully.
Most importantly, his experience demonstrates that career mobility, when approached strategically, can accelerate professional growth and lead to increasingly satisfying roles that align with personal values and career goals.
This blog post summarizes insights from Guidance Counselor 2.0, a live streaming show hosted by Taylor Desseyn that explores career development in the tech industry. Find more episodes of the show here: Guidance Counselor 2.0