Red Flags and Green Flags: What Engineers Actually Need to Know About Getting Hired

Matt Glickman posted a senior engineering role on Monday. By Tuesday morning, 500 applications sat in his inbox. Maybe 50 would get a real look. Five would turn into phone screens.

Glickman is a Senior Technical Recruiter at AcuityMD. He’s hired engineers, data scientists, and PMs for more than a decade, including stints at GoodRx, Upstart, and Wonders. At ReSci (acquired by Constant Contact), he was the first internal recruiter—building the hiring function from scratch.

In January’s Ask a Recruiter session, he broke down what actually makes a difference for candidates. Not polish. Not hustle theater. Just the things that help you stand out when time and attention are limited.

🎥 Watch the full session on YouTube

The 10‑Second Resume Test

“The person looking at your resume has absolutely no idea who you are.”

Recruiters don’t read resumes. They scan them.

You wrote yours with context in mind—projects, tradeoffs, backstory. The recruiter has none of that. Just a PDF and a job description. Your job is to make the most important signal obvious immediately.

What works:

• One clear impact metric near the top (in bold)
• Short bullets, not paragraphs
• White space that lets the eye move quickly

Glickman shared an example that worked instantly: a resume that opened with a single line—“Reduced average page load time by 3 seconds.”

That tells a full story in one glance. You understand what matters to the business. You shipped something measurable. You made things better.

What slows you down:

• Long summaries at the top
• Dense paragraphs describing responsibilities
• Skills lists that aren’t relevant to the role

“If Apple were making a resume for itself,” Glickman asked, “would it look like this?”

If the answer is no, simplify.

Apply—Then Do One More Thing

Submitting applications at scale doesn’t help much on its own. What you do after you apply matters more.

At startups especially, it’s usually possible to find:

• The hiring manager
• Someone on the same team

Reach out on LinkedIn with a short message. Two or three sentences is enough:

“Saw you work at [company]—noticed you’re hiring for [role]. I’d love to hear what your experience has been like.”

You’re not pitching yourself. You’re starting a conversation.

Short, human messages tend to get read.

Make Career Transitions Obvious

Recruiters pattern‑match fast. Sometimes too fast.

If your most recent role says “software engineer,” and you apply for a PM role, many recruiters will assume you’re not a fit—and move on.

Don’t make them guess.

Add one clear line at the top of your resume:

Software engineer transitioning into product management, leveraging technical background in customer‑facing work.

That single sentence can stop an automatic rejection.

The same applies to other transitions:

• Big tech → startup
• Backend → product‑focused role
• Domain switch

Say what you’re doing and why. Briefly. Explicitly.

And when you can, find someone at the company who’s made the same move. People recognize themselves in your background—and they tend to help.

Interviews Are for You, Too

Later‑stage interviews aren’t just about proving competence. They’re about figuring out how the company actually works.

One simple tactic:

Ask the same collaboration question to different interviewers.

For example:

• Ask the engineering manager how they work with product
• Ask the product leader the same thing

If the answers line up, that’s a green flag.

If they describe totally different realities—different processes, different expectations—that’s useful information. It doesn’t mean “run.” It means pay attention.

You’re not looking for perfection. You’re looking for alignment.

How to Talk About Growth (Without Raising Flags)

There’s a difference between wanting support and signaling you’ll need constant direction.

This works:

• “What does mentorship look like here?”
• “How do you help people ramp and succeed?”

This doesn’t:

• “I’ve never done this before—who’s going to teach me exactly how to do it?”

Startups need people who can try things, hit walls, adjust, and keep moving.

On the flip side, total independence can also be a red flag.

“I work completely on my own” often reads as “I don’t communicate.” Strong teams need collaboration—not just output.

Clarify Remote Expectations Early

Job postings don’t always keep up with reality.

A role might be listed as remote, but halfway through the process you learn the team expects people in‑office a few days a week.

Ask directly on the first call:

• Is this role remote, hybrid, or in‑office?
• How often do you expect people on‑site?

Get clarity before you invest weeks in the process.

The Big Takeaways

• Your resume gets seconds, not minutes—lead with impact
• Apply, then message someone on the team
• State career transitions clearly instead of hoping recruiters infer them
• Use interviews to test alignment, not just impress
• Ask about remote expectations early

None of this guarantees an offer. But it does increase the odds that your application actually gets read—and that the role you land is one you’ll want.

This article summarizes key points from Wellfound's 'Ask a Recruiter' live Q&A event featuring Matt Glickman, Senior Technical Recruiter at AcuityMD. To find out more candidate tips, check out other 'Ask a Recruiter' sessions on the YouTube playlist here