Pain Letter 101

Pain Letter 101 - Career Makeover Academy

Welcome to "Pain Letter 101"!

Trying to find a job is hard work.

They call it a “job hunt” for a reason!

There are so many pieces to the job-search puzzle:

  • Thinking of places that may have job postings you can check
  • Networking and putting yourself out there to make valuable connections
  • Reaching out to the network you've already established to see if they have any leads that would be a good fit. 

One way to set yourself apart and create opportunities is by creating a ‘Pain Letter’.

These letters are essentially just identifying an area that a business or department could use improvement on or needs help with (their pain point).


Highlighting why YOU are the person to fix it for them.

I know, I know, this seems like a LOT of stuff to wrap your head around!

Especially, when you’re already knee-deep in the job search world.


If you’re not already familiar with the concept of a pain letter, you’re probably brimming with questions like:

  • How do I write a pain letter?
  • What should my pain letter contain??
  • How long should my pain letter be?!?
  • Should I simply re-tell my story in the pain letter???
  • What about discussing my resume?!?!?


Take a deep breath, calm down.


If you’ve had ANY of these questions don’t worry, Career Makeover Academy's got you covered! 

For other resume alternatives check out our article '7 Alternatives to a Boring Old Resume'

Pain Letter 101 - Career Makeover Academy

Pain Letter 101: The Question

This blog post was inspired by a question that someone asked in my Facebook community #LevelUp Your Career.

I am looking for work, and am trying to network (I am an introvert but can manage OK) and am using online job boards to look for work. I am also contacting friends that may be able to give me inside information -- but that's 50/50 as not everyone wants to "risk" putting you forward (for whatever reason).

So the next step, and maybe I should have done this all along is to start contacting companies that would be interesting to work for. I've read about pain letters (aka opportunity letters) - but how do I even write one? How do I find key decision makers or people in some of those companies?

I know I can use LinkedIn but what other resource? What should the letter contain? How long should it be?

Once I identify key people - maybe a VP or Director of Customer Operations, how do I prepare the pain letter? Is the pain letter simply re-telling my story (or resume)?

What else can I do to find work? I'm not sure if I'm doing too little, or just the right amount. 

I've seen companies that "blast" resumes out - but that does not seem like a good idea...

 would love your insights.

 — feeling overwhelmed

... is the pain letter different if I'm contacting a CEO vs VP vs DIRECTOR?

Having reported to a VP and DIRECTOR previously they don't want a lot of "fluff" but the facts quickly. How do you quickly get your point across so that they think "hey, I can use Mo here - let me call him today"???

Download your Pain Letter Cheat Sheet Here!


Pain Letter 101

We’re going to break down EVERYTHING you need to know about a pain letter, so you can craft the PERFECT letter and get yourself that dream job.

First, let’s take a look at what a pain letter is and how it applies to your job seeking process.

Pain Letter 101: The Answer

So, What IS a Pain Letter, Exactly?

A pain letter's nothing more than you talking about a hiring manager’s biggest problem and offering a solution to it.

Not to be confused with a cover letter, a pain letter isn’t JUST a summary of your skills.

It’s a letter that shows a hiring manager that you have the skills they need to make their job easier.

Every company has a pain point.

Whether it’s a college trying to increase donations, a large company with lots of red tape that causes it to be slow to act, clients frustrated with hold times to speak with customer service representatives...

There’s ALWAYS a pain point to be found. 

A pain letter addresses this pain point, and outlines exactly how you can solve it. 

What’s Included in a Pain Letter?

A pain letter usually has 4 points you want to hit on:

1. A Hook

Pain Letter 101 - Career Makeover Academy

This is usually something positive or congratulatory.

You might want to learn some copywriting/marketing techniques to help you come up with a great subject line.

The hook is what grabs the hiring manager’s attention and makes them want to keep reading.

2. The Pain

Pain Letter 101 - Career Makeover Academy

This is the issue that the manager needs a solution for.

Your pain letter should address all of the key points of the issue.

This shows the manager that you know what you’re talking about.

3. The Solution

Pain Letter 101 - Career Makeover Academy

You should provide a brief outline of how you would handle their pain point given your experience and expertise.

4. The Conclusion

Pain Letter 101 - Career Makeover Academy

To wrap things up, let them know that you’d be happy to speak with them more if the solution you proposed was of interest to them.

The actual content of each letter will be different depending on who you are addressing.

A CEO, VP, Director, and Team Leader/Manager would all have different concerns and pain points.

It’s important to tailor your response to each person you’re contacting.

How Long Should a Pain Letter Be?

Pain Letter 101 - Career Makeover Academy

Pain letters should be short and concise.

Keep them to only a few paragraphs long - 4 at the most.

One paragraph for each point you want to hit.

Since most of these letters will be sent via email, page length doesn’t matter--go based on paragraphs instead.

How Do You Find the Pain Point?

Pain Letter 101 - Career Makeover Academy

There are a few ways you can approach this.

Your first option is to speak with someone in person that has insight on the company you’re interested in.

The best way is to reach out to someone who works under the hiring manager and conduct what’s called an informational interview.

Invite them for coffee or a quick phone call, explaining that you’re interested in applying for a position at their company and would love their help.

That last part’s important - you want to make sure you’re very clear in the fact you are asking for help “I’d love your help...” or “I was hoping you’d be able to help me out…”.

You could also reach out to several people who work at the organization and ask what their biggest challenges are.

If you can’t get anything from the horse’s mouth, so to speak, you can research online.

A few places you could look are the company website, Glassdoor, LinkedIn, and other social media platforms.

See if there's any big news about recent or impending layoffs, new product lines, an acquisition or spinoff…

Essentially, you’re putting on your detective hat to see if the company is dealing with any major issues or challenges.

Put yourself in a manager’s position and come up with a pain point they’d likely be dealing with.

Once you’ve completed your research, you can use that information to come up with a solution based on your past experience and area of expertise.

You want to show the company/hiring manager that you have what it takes to make their lives easier.

At the end of the day, that’s all any manager really wants!

Finding People on LinkedIn

Pain Letter 101 - Career Makeover Academy

When doing your research, you want to find the right person to send your letter to.

The best way to find people is through LinkedIn.

Enter the company name into the search box, along with any keywords you think would best describe the title of the hiring manager or person heading the department you’re interested in joining.

After your search is completed, you’ll see a few advanced search options.

Click on “People” so that you only see people’s names instead of groups or companies.

Also, check “Current Company” so that you’re only viewing people who are current employees of the organization.

And then take a little scroll through the list.

See someone who looks like the obvious person?

Well then, you’re in business!

Decide how you’re going to approach and reach out directly.

If you’re interested in startups, you might want to check out

It may seem a bit daunting at first, but trust me--a good pain letter can be worth it's weight in gold.

When done correctly, pain letters can result in callbacks up to 25% of the time, according to Liz Ryan, Founder and CEO of The Human Workplace.

It boils down to doing good research on the company you want to work for, figuring out an area they need help in, and writing a great letter to show them why they can’t live without you. 

Pain Letter 101: The Cons

Pain Letter 101 - Career Makeover Academy

There an also be some drawbacks to pain point letters. 

If you aren't actually addressing an existing pain you might come off as pretentious.

Also, some hiring managers find them to be a bit invasive and, dare I say, creepy.

Alison Green at advises against them, stating "I’d advise against them. When I’ve received them, they’re generally cringingly off-base and sound like they were written by someone who will be all flash and no substance."

Keep in mind that this is just one manager's view.

And, much like anything else in life, you can please some of the people all of the time, you can please all of the people some of the time, but you can’t please all of the people all of the time.

Aka - what one manager hates another one will love.

So, no matter which way you go make sure to do your best and your efforts will eventually be recognized by a manager who will appreciate you for what you bring to the table!




Have you ever sent a pain letter? Did it work for you? Comment below!


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Stephanie Berchiolly

Teaching you the skills to get a new job or change to a career that you love.