Do You Still Need a Cover Letter in 2025? My Real Experience Will Surprise You

Why Reddit is wrong about cover letters being dead - and how one personalized cover letter changed my entire career

If you've spent any time on Reddit lately, you've probably seen the heated debates about cover letters. From r/recruitinghell claiming "Cover letters are a waste of time" to r/jobsearchhacks asking "Do we still need to write a cover letter for EVERY job in 2025?" - job seekers are more confused than ever.

I used to think cover letters were pointless too. Then I learned the hard way that it completely depends on the situation - and how you write them.

Let me share two real stories from my own job search that completely changed my perspective on when cover letters matter and when they don't.

When Cover Letters Don't Matter: My First Job Story

The Property Management Position That Required Zero Effort

My first job was as a Data Analyst/Senior Financial Analyst at MD Squared Property Group, a full-service property management firm in Manhattan. Here's exactly how I got it:

My friend and classmate Alex worked there and had just jumped to a higher position at another company. MD Squared was desperately scrambling to fill his role - they needed someone who understood both the financial side and data analysis for their growing portfolio of NYC buildings.

When I applied, they didn't ask for a cover letter. They barely even read my resume.

The Co-founder's exact words to the CPO were: "Save time reading his resume - he's Alex's 'twin brother.'"

I got hired and stayed there for over 3 years (Jan 2019 - May 2022), eventually managing financial analysis for their entire property portfolio.

The Reality Check: When companies are desperate to fill a position and you have an internal referral, cover letters become irrelevant. The hiring decision is based on trust and urgency, not your writing skills.

When Cover Letters Change Everything: My Career-Defining Moment

The Senior Data Analyst Position I Had No Business Getting

After spending 3+ years in property management finance, I wanted to transition into pure data analytics. I applied for a Senior Data Analyst position at Progressive Leasing. Here's the problem: while I had strong analytical skills from my Master's in Data Analytics & Visualization from Yeshiva University, I had zero experience in the lending/leasing industry.

On paper, I was a risky hire. My resume showed property management experience, not consumer lending analytics.

But I spent hours crafting a personalized cover letter that did something different. Instead of listing my experience, I focused on how my specific skills and personality traits made me the perfect fit for their unique challenges and company culture.

I researched the company thoroughly, understood their pain points, and explained exactly how my background - even though it wasn't traditional - would solve their specific problems.

The result? I got the interview. Then I got the job.

I've now been in that Senior Data Analyst position at Progressive Leasing for over 3 years (May 2022 - Present), and my boss still remembers that cover letter as the reason they decided to give me a chance despite my non-traditional background.

The Lesson: When you're not the obvious choice, a personalized cover letter can be the difference between getting rejected and getting your foot in the door. My career progression: How different cover letter strategies led to different outcomes - from internal referral success to cover letter-driven career transition.

The Problem With Generic Cover Letters

Here's what I learned from these two experiences: generic cover letters are worse than no cover letter at all.

You know the ones I'm talking about:

"I am writing to express my interest in the [POSITION] role at [COMPANY]. With my X years of experience in [FIELD], I believe I would be a valuable addition to your team..."

These templated cover letters don't help you stand out - they make you blend in with everyone else using the same generic approach.

The Reddit Debate Makes Sense Now

Looking at all those Reddit threads about cover letters being "pointless" and "time-consuming," I finally understand why people are frustrated. They're writing generic cover letters that add no value, then wondering why they're not getting responses.

Of course generic cover letters feel like a waste of time - because they are.

What Actually Works: The Personalization Strategy

The difference between my two job experiences taught me this: personalized cover letters can be game-changers, but only when you're competing against similar candidates or need to overcome obvious gaps.

Quick reference guide: When cover letters are essential vs. when you can skip them based on your specific situation.
When You DON'T Need a Cover Letter:

• You have a strong internal referral

• The company is desperately hiring

• Your resume perfectly matches their requirements

• You're overqualified for the position

• The application explicitly says "no cover letter"

When You ABSOLUTELY Need a Cover Letter:

• You're changing industries or roles

• You lack some required experience

• You're competing against many qualified candidates

• The role emphasizes communication skills

• You need to explain gaps or unique circumstances

• The job posting mentions "cover letter required" or "tell us why you're interested"

The Modern Solution: AI-Powered Personalization

Here's the thing - I get why people hate writing cover letters. Crafting that personalized letter for my data analyst position took me 3 hours of research and writing.

But that was over 3 years ago when I was manually crafting my cover letter for Progressive Leasing. Today, we have tools that can do the heavy lifting.

Option 1: ChatGPT with Smart Prompts

You can use ChatGPT to write personalized cover letters, but you need the right prompt structure. Most people just ask ChatGPT to "write me a cover letter" and get generic garbage.

The secret is in how you structure your prompts to get truly personalized results. I'll be sharing my exact ChatGPT prompts that create compelling, personalized cover letters in my next article - stay tuned!

Option 2: Purpose-Built Tools

Having spent hours crafting that career-changing cover letter for my current role, I realized there had to be a better way. That's exactly why I built https://ai-coverletter-generator.com/ - to solve the same problem I faced when transitioning from property management to data analytics.

The tool analyzes job postings and creates personalized cover letters in about 30 seconds, focusing on the specific requirements and company details that generic tools miss. It pulls information directly from the job posting URL, so it catches details that get lost when you copy-paste job descriptions.

I created this because I remember spending 3 hours researching Progressive Leasing and crafting that perfect cover letter. Now, candidates can get the same level of personalization in under a minute.

The Real Answer: It Depends on Your Situation

After going through both experiences - getting hired without a cover letter and getting hired because of one - here's my honest take:

For roles where you're the obvious fit: Skip the cover letter unless explicitly required. Focus your time on applying to more positions. For roles where you need to stand out or overcome gaps: A personalized cover letter can be the difference between getting rejected and getting interviewed. For everything in between: If you can create a personalized letter quickly (using AI tools or templates), include it. If it would take you hours to write from scratch, your time might be better spent applying to more positions.

Your Action Plan

Audit your current applications: Are you sending generic cover letters? Stop immediately. Identify your situation: Are you the obvious choice for most roles you apply to, or do you need to overcome gaps/competition?
Choose your approach:

• Strong fit + internal referrals = Skip the cover letter

• Need to stand out = Invest in personalized cover letters

• Everything else = Use AI tools for quick personalization

Test and track: Apply your approach to 10 jobs and measure response rates. Adjust based on results.

The Bottom Line

Cover letters aren't dead in 2025 - but generic ones should be.

The Reddit debates about cover letters being pointless make perfect sense when people are spending hours writing templated letters that add no value. But when you need to differentiate yourself or overcome obvious gaps, a personalized cover letter can literally change your career trajectory.

The key is knowing when to use them and having the tools to create them efficiently.

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Ready to test this approach? Pick one job where you're not the obvious choice and create a truly personalized cover letter that addresses their specific challenges. You'll immediately see why personalization matters more than the tool you use to create it.

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About the Author

Randy Xia is a Senior Data Analyst at Progressive Leasing with over 6 years of experience in financial analysis and data analytics. He holds a Master's in Data Analytics & Visualization from Yeshiva University and a Master of Accountancy from Missouri Southern State University.

After successfully transitioning from property management finance to consumer lending analytics using a strategically crafted cover letter, he created AI Cover Letter Generator to help other professionals make similar career transitions more efficiently. He currently lives in New York and specializes in using data to drive business decisions in the fintech industry.

Connect with him on LinkedIn