The Resume That Gets What It Gives
- Aug 5
- 9 min read
Updated: Aug 7
Dear Readers,
Lots has and will be written about the resume until it fully dies. It’s a recurring rite to fiddle with our resumes in any job market. Even more so now when you long for a magic bullet to pass through the noise into a hiring manager’s hand.
And there kind of is—for cold applications, your best bet will always be telling your story in your words. Even the act of unearthing this story sets you up for the networking and interviewing that bookend the process of getting hired.
So pull up a seat for my take based on ~20 years in tech hiring and career coaching.
The resume is a teaser.
Your resume is not your biography; it’s more like the book jacket. It needs to tell the reader just enough so they know whether they want to spend more time with you.
As you write your resume, picture someone reading it, getting excited, and sending you an invitation to connect. The same things that make you want to spend time with a book—being interesting, memorable, aligned—apply here.
To craft this kind of resume, you may need to set aside the advice out there.
Most resumes share a fatal flaw—they could belong to anyone.
After reading thousands of resumes, the majority of those are nearly identical if I filter by job title and years of experience. While it would be easy to say this flattening is all about AI, the ATS, or the AI ATS—This has been a long-standing problem.
We’ve all accepted and copied the format passed down to us.
But when you mold to a template and tailor to a job description, it strips away your narrative. Now the rich career story that took years to build loses the strange pivot, the obsessions, and the lessons. It becomes a list of tasks and out-of-context metrics.
It sounds like everything and nothing. So for me, on the other side, reading these resumes becomes hypnotic; it all blends together.
The result is a lot of resumes are hard to reject, but equally hard to champion.
This leads to the “in the middle” problem—your resume matches the need, but also looks like everyone else, so you end up in limbo, which means you may never hear back.
Like with the book jacket, you want someone to feel an immediate yes or no. Otherwise it goes to the middle—the just in case or someday pile.
The reason is uncertainty. Everyone in the hiring process is trying to de-risk the hiring decision while facing real restraints on how many candidates they can seriously consider.
Distinctiveness reduces uncertainty, but most resumes are not distinct.
The things holding most people back from being distinct are the fear that if they break the mold or don’t list everything they’ve done, they’ll miss out on job opportunities. But the glob of keywords makes it hard to remember and advocate for you.
What I want to know is…
(1) Your Origin:
How did you get into this role, field, or industry? Why have you stayed?
(2) Strengths:
What are you unusually good at? Where do you thrive? How does that tie to 1 & 3?
(3) Problems you solve:
In what state was a company or team when you joined? What pains and problems did you find and solve? What did you learn? What was the reception?
(4) What’s next:
What do you want next for your career? Why this role? Why now? Why us?
This is what my brain sounds like when I'm scanning a resume to see if it matches the company's need. With more and more careers looking like portfolios or gallery walls; I care way more about problems solved than timelines and tenure.
I’m looking at the work and the circumstances. There are nuances that never make it to the job posting about the manager, culture, team. For instance, if you had a big team and budget, that’s probably not right for a bootstrapped startup. If you keyword vomit instead of giving me your career retrospective, I may be missing information that I need.
Think of it this way, you know your whole career story, I know nothing. The resume's job is to bridge that gap by ensuring the important parts are impossible to miss.
If you’ve done 1-4 you de-risk your candidacy and I assume you’re thoughtful.
Put yourself in the shoes of the hiring team
Recruiters and hiring managers have a bad rap; sometimes that's earned. I’ve slogged through some weird situations myself, including a three-hour interview where I was the “wrong Courtney.”
But they're still the gatekeepers who ultimately want to find the best match to fill the role. Make it easy for them.
Try to imagine that you are reviewing your resume for a role.
What information do they need?
What in your story may be confusing or worrisome?
Are there any gaps in your experience or timeline?
You’re selling yourself. So just as book jackets use bold typography and color or provocative titles—you’re trying to break the trance.
A lot of folks try to combat this trance with data or metrics to prove their impact, but data without narrative is just numbers. Hiring teams rarely know the company context or your role in taking a company, team, or project from point a to b. It’s not bad information; but it’s sitting in isolation; hence why I’m obsessed with people who give me the company low-down.
I can tell when someone has written a resume for the hiring team, because everything is spelled out almost like an FAQ. (Honestly, I would love to receive an FAQ resume.)
FAQs
How long should my resume be?
One-page! My ideal is a one-pager written like an FAQ in three sections of who you are, what problems you’ve solved, and what you want to do next. If you add a second page—I’d make it a case study, especially if it's for a senior role.
What if I'm not unique?
But you are! Everyone brings a unique lens that’s built from childhood and evolves with each new experience. Set a 25-minute timer and jot down any belief, skill, value, trait you can think of spanning your life. I promise there is a through-line in there, which can become part of your narrative.
Should I list every job?
No. If you’re entry-level, include any work, internships, or group projects. But once you surpass 10-years, it’s time to get picky or summarize. Address any gaps* in the timeline, but consider leaving off anything older than 10-years.
I like to summarize the first half of my career with a statement like—Additional experience: I’ve held every role in People & Culture, which helped me learn the ins and outs before owning the function and big picture. *Companies can be assholes about job gaps. The language and packaging matters. As someone who has taken three micro-retirements due to burnout, I frame it as I'm choosing to come back to the job market. Something like, After a planned sabbatical to spend time with my daughter or tinker with a side project—I'm ready for a challenge.
If you were let go or laid off, you can still package the gaps, and it's a resume so you don't need to do much. Something as simple as after a company restructure, you chose to recalibrate and reflect, and now you're back on the market.
How do I show I can do everything in the JD?
You don’t! Focus on your story and the problems you solve. Everyone is primed to remember narratives more easily than isolated details.
If you want to tailor to the job description, don’t inject keywords left and right. Instead, look for potential challenges that the company may be facing.
When I submitted resumes for Head of People roles, instead of listing every thing in that realm, I would focus on a problem I knew they could or would have. So, if they just got Series B funding, I would focus my resume narrative on hiring challenges at the Series B stage, even though I could do more.
It’s the book jacket theory. I was pitching myself as a salve for a problem they were bound to have, and that got me the interview to address everything else.
Final note on this one—Titles carry hidden context. Most recruiters make assumptions about ownership and skills based on titles. So if your title is non-standard—I’d zhuzh it up to industry norms. Example: Marketing Associate IV might be a Marketing Manager at most companies. Use the latter.
Do I need to customize my resume by role?
No. That’s the beauty of writing a resume that represents your story first and foremost. If you want to customize, see above. 👆
What about the ATS or AI?
These tools have existed for a long time. Sometimes they are used as a filter, and sometimes they’re not. People hire people, so my best advice is to write your resume for a person to read.
Should I do a cover letter?
Always complete anything that an application asks for like a cover letter or pre-screen questions. Here are ways you could use that space:
Address anything that might make you a risky candidate.
Example: I never worked in the same industry twice, which was risky. I always addressed it early before they could by naming that after being a Head of People for so long, learning new industries kept it challenging.
Share something unique about yourself—A short anecdote beats the kitchen-sink.
Example: Earlier in my career, I wrote a cover letter about planning my sister's wedding. It included negotiating on a tight budget, the planning phase, and how I adapted when a theme change meant finding black roses in the final hour. It's hard to forget the Buffy the vampire slayer story.
If you happen to be emotionally drawn to the company—share that!
Example: When I worked at Match Group, we remembered the resumes from people who had found love through our dating sites. We knew they had a special connection to the customer and product. It makes hiring teams feel like you're more likely to care about and stay at the company.
How should my LinkedIn differ from my resume?
If you include your LinkedIn on a resume, ensure that it’s up-to-date and there’s enough overlap with your resume to feel above board. And since you have more space on LinkedIn, here are a few things you could do with it:
Create a headline with a relevant title + something you’re known for. Our co-founder Kelsey used to have “singing recruiter” as hers.
Write an About Me: what you’ve done, what you believe, what’s next.
Feature any posts or articles written by you that embody your POV.
Add all your professional jobs, even the ones from 10-20-30 years ago. This could help with potential connections and show more breadth.
Attach articles, press, awards to your jobs for impact. You can also elaborate within each job—don’t go verbose city, but a greatest hits list is nice.
Share, like, repost things that connect with. But don’t feel obligated to participate in the social part of LinkedIn.
All of these suggestions can also help you be discovered by hiring teams, but it's only one lever. LinkedIn is showing signs of strain, and we will likely see their hold on recruiting fade. Hiring teams are weary of high fees and hollow applications, while candidates distrust ghost jobs and the algo.
What else can I do to stand out?
Ask for help. Reach out 1:1 to people you’ve worked with and ask for intros to hiring managers, recruiters, new opportunities. Even if they aren’t hiring for a relevant role, getting their perspective can be enlightening.
Write a half-page FAQ about you that others can share.
About me:
One-sentence on your career, industry, and values.
What I’ve done:
Pick 3-5 really cool bullet points from your resume and put them here. It should be the things that you’d be stoked to do again. Add a little context if needed.
What I’m looking for:
List out preferred jobs, titles, industries, ownership.
What I’ve learned:
This is the strategic partner to what you’re looking for—add insights on where you thrive, ideal environments, the company stage you’re best at, what a good manager means to you (either having one or being one), etc.
How to help:
This is a note for your friends, something like "Share this with anyone in your network that’s a founder, leader, hiring manager, or recruiter for these roles."
A lot of recruiting agencies use a similar format to pitch their candidates, so make it easy for your friends and colleagues to pitch you.
Do you have a resume checklist?
Yes! If you can answer yes to these questions, you're doing it!
Could a former colleague identify this as your resume?
Is the resume focused on the pain and problems that you solve?
Does your resume feel more like a story than a timeline?
Have you qualified your impact and data with context? Could anyone understand the challenge a company, customer, team was facing?
Did you write this resume yourself? Is it free of senseless jargon and AI?
Is it clear how the job, role, company benefits your career?
Have you messaged everyone who can support your job search?
If you're not sure, email me. I'll give you my take.
I’ve thrown a lot at you, but I hope this is helpful in navigating the wide world of applications.
Some of the best hires I’ve ever made were from cold applications and the one thing they all had in common was I knew within seconds that I wanted to talk to them, because they wrote a story that was hard to forget.
Some had bullets, keywords, and fluff, most didn’t, but it didn’t matter, because all I needed was the who are you, what problems you solve, and why you want this job.
xoxo,
Courtney
Want access to more resources like this and your own coach to reflect with you?
p.s. If you’re a job seeker, here are some recommendations:
Reflections to ground your job search. Sometimes we need a moment to pause before reentering the application game.
How to answer Tell Me About Yourself. This also works for cover letters, prescreen questions, or LinkedIn bios.
Building a Personal User Guide (PUG). These questions can help you see yourself holistically and prepare you for interviews down the line.
