Executive Job Search After 50: The Complete Guide to Resumes, LinkedIn & Overcoming Ageism

I’ve been thinking a lot about how to best support this community of 100,000+ through what has turned into one of the most challenging markets that we have seen.

Over the past several years, I've shared more than 1,000 LinkedIn posts on executive job search strategies and have been fortunate to contribute insights to publications including The Wall Street Journal, NBC News, Forbes, Fast Company, Business Insider, CNBC, MarketWatch, AARP, and other leading news sources.

Rather than making you search through hundreds of posts, I've pulled together my best advice in one place. Whether you're updating your resume, optimizing LinkedIn, or navigating ageism, this guide is designed to help you land your next leadership opportunity.

Table of Contents

1. Start With Your Career Strategy
2. Resume Strategy
3. LinkedIn Optimization
4. Countering Common Job Search Issues for Gen X and Baby Boomer Job Seekers
5. Additional Executive Job Search Resources (Ageless Careers Toolkit)

Start With Your Career Strategy

Before you sit down to write your resume …

I want you to use this process to build your confidence.

We’re going to really think about all of the great work that you have delivered.

We’re going to take the time to highlight your results in a clear and concise way.

So many times, my clients don’t want to brag about their results.

For this process to be successful, I need you to stop and own your results. You have delivered value to your employers and I know that you can deliver value to future employers. But you need to take the time to write it out and own it.

I want you to catch the employers’ eye with an awesome resume, but I also want you to internalize and know your value so that when you go into that interview, you are ready. You’re going to be confident in your skills and ready to go.

Before we start, I’m going to assume that you have defined your career goals. If you haven’t defined your career goals, then please go back to “Build Your Ageless Career” to set your career goal before you sit down to write your resume.

99% of the time, you will not need different versions of your resume. Yes, you can make small tweaks based on each job, but your resume base should be enough and your changes shouldn’t take more than 5 minutes.

Resume Strategy

Here are 5 quick tips to think about as you get started:

1. Review job descriptions: You've got to understand the language that the hiring team is speaking, so note the skills and keywords that are most important and focus your resume/LinkedIn in these areas.
​
2. Brain dump: Rome wasn't built in a day and your resume won't be either. Take 5-10 minutes per day to jog your memory on past accomplishments (pen and paper is fine).
​
3. Look it up: If you have access to reviews/emails/etc, scan those files and make a note of your biggest highlights and impacts. (And if you think that you may be laid off soon, grab those details now).
​
4. Google yourself: This might sound silly, but you want to see how you are showing up. This also might help you to jog your memory on presentations, etc that you might not be giving yourself credit for.
​
5. Give yourself grace: It's going to take a little bit of time to do all of this - especially if it's been awhile since you've updated your career documents.What are your biggest career accomplishments and why?

As you're getting started, ask yourself what skills would you like to emphasize in your resume? (Hint: those should be aligned with the jobs that you are apply for – review those job description closely)

Do you have any volunteer work (aka community leadership), presentations, publications, patents, board work, or other areas that you currently aren’t giving yourself credit for in your resume and LinkedIn profile?

Bonus tips:

If you are looking for a “promotion” or jump in title (let’s say you want to move from Director to VP), then be sure to discuss how you currently do VP-type in your current role. Make sure to spell out how you advise VPs and/or highlight if you are reporting to a VP.

Be careful about getting stuck in a resume feedback loop – it’s good to have friends and/or peers review your resume, but if you have 10 people review your resume, you’re going to get 10 different opinions. Just because someone says that they wouldn’t do it that way, that doesn’t mean that you should change what you have. However, if you’re not getting results, it makes sense to revisit what you have.

Resume FAQs

How do I talk about early career work experience?

The answer is: it depends.

Is the early experience relevant to the roles that you are applying for?

Is it with a “big name” company?

Is it work that you would like to emphasize?

If the answer is NO, then you can choose to keep it off of your resume and we can discuss this as a brief career note at the end of your resume and share this without the years that you worked. Examples:

Experience includes roles as Project Manager for ABC Company and Business Analyst for XYZ Corporation. Highlights include managing team of 10 to drive 10% reduction in quality defects.

Experience includes various IT roles with ABC Consulting. Key accomplishments include delivering $10M technology upgrade for global Fortune 50 transportation leader (FedEx).

Experience includes HR leadership roles with Westshore Electronics and HP.

If the answer is YES, then we can discuss this experience in more detail, highlighting this experience in your Executive Summary and Experience sections. Here’s an example:

Experience includes leading roles including Senior Vice President, Marketing & Promotions for Fortune 500 Company and Marketing Director for ABC Corporation. Key highlights include:

· Spearheaded $8 million advertising sponsorship, partnering with leading consumer brand.

· Drove thought-leadership and created an advisory board and event series with prominent keynotes.

· Sponsorship development drove billions in advertising revenue for multiple networks.

· Developed integrated media sponsorships, custom content, and brand integrations; included award-winning programs.

· Strategies generated millions in revenue and significant earned media promotion.

· Directed publicity and promotions for a location-based entertainment concept, including crisis management strategy.

How do I discuss my career break on my resume?

I use a Career Note to discuss career breaks on resumes.

Career Note: Currently working on consulting project for XYZ Corporation. Highlights include driving 10% sales growth through optimizing online media strategy.

Career Note: Completed volunteer work with North Hills Community Outreach and completed PMP coursework from 2021-2022.

Career Note: Was on caregiving leave from 2014 – 2017, serving as McKnight Elementary School PFA President. Led $25K fundraising campaign to purchase new playground equipment.

MILITARY EXPERIENCE: Experience includes roles as HR Specialist and Recruiter with United States Navy and United States Army Reserves. Held Top Secret SCI Security Clearance. Won numerous awards for service.

You will see several examples at the end of this guide to show how to incorporate these into your resume.

How do I talk about consulting projects that I completed during my career break?

You can talk about these consulting projects as a career note (see above) or as a separate section (see my resume in Example 1 for how I discuss my work as an Independent Contractor). I think either of these methods are fine – if you don’t have a lot of room, then the career note should be OK. If you are looking to emphasize this work, then you can list this work out as a separate section. You can create a LinkedIn business page so that this work appears more cleanly in LinkedIn.

How do I write a career change resume?

If you are looking to change careers, you are going to have to show how your transferable skills will apply to your new role.

Let’s say that you are looking to move from engineering to financial analyst: you are going to emphasize all of the skills that you used as an engineer (i.e. problem solving, project management, analytics, research, etc) and show how you will use those skills in your goal role.

One quick job search hack is to filter job postings and look for those that consider "transferable skills" - this will give you an idea of companies that are actively accepting career changers.

How do I target remote roles?

As I’m sure that you have heard, the number of remote roles is declining dramatically.

If you are looking to land remote work, you need to show how you have succeeded in a remote work situation in the past.

Be specific! Say things like:

· Formed new remote organization, coaching team of 15 new direct reports and building collaborative group with focus on teamwork and communications.

· Built cross-functional relationships in remote work environment, setting goals and clearly identifying growth opportunities.

How do I target part-time roles?

I typically use FlexJobs when looking for part-time roles (there is a cost to join, but if you want part-time work, it is a good source of jobs). If you have previously worked on a part-time, flexible, or contract basis, I would discuss this:

· Evaluated admissions applications for Top 20 MBA program, providing support on a seasonal basis.

· Drove success for healthcare start-up in part-time role, serving as social media subject matter expert.

How do I discuss a short-term job on my resume? What if the role wasn’t a fit and I left the job quickly (i.e. within a few weeks/months)?

This happens all of the time. I would prefer that you discuss the role in some way on your resume – this is a lot more common than what you think it is and I believe it’s better to show this (versus hide it or pretend that it didn’t happen). I would discuss it as a career note – when you go into the interview, I would not speak negatively about the employer, but would briefly frame what you learned from the role (and emphasize how you can use those learnings in your new role if you can do so).

How do I transition from entrepreneurship?

Entrepreneurs re-entering the paid workforce can give employers pause for a number of reasons. Employers will wonder:

Can I pay you enough?

Can you take direction as an employee (vs giving direction as an entrepreneur)?

Will you leave when something better comes along?

How will your entrepreneurial experience translate to the new business?

Here are my tips:

1. Narrow your search: you could probably go in a lot of different directions, but be clear on the types of roles/companies that you are targeting.

2. Demonstrate how you can solve the employer’s pressing issues: as an entrepreneur, one of your superpowers is solving problems. Closely read the job description and research the company’s current situation. Outline how you can step in and drive growth, cut costs, etc.

3. Tackle the elephant in the room in your cover letter, LinkedIn, and interview: be transparent about your goals and counter potential concerns throughout the process. Show that you are committed to building relationships.

4. Be careful about using lofty titles: You might have been CEO of your company, but some companies are going to be afraid of the CEO title – especially if you are targeting a VP or below role. Don’t be afraid to change your title in your resume and LinkedIn so that it’s closer to the title that you are targeting.

Should I use a functional resume format?

I don’t recommend using a functional resume format

Use your Executive Summary to summarize your experience and show the common threads in your experience. If you really want to, you can use a “Selected Career Highlights” section

How should I break out my experience if I have been with the same company for a long time?

Can I show multiple roles together? Answer: It depends!

Our goal is to position you for your target roles, so you always want to highlight the experience that aligns with your target.

You can break out experience in projects or with bullets – whatever you feel tells your story best.

Should I show my hobbies on my resume?

Unless your hobbies/interests are aligned with your goal role, I don’t recommend it.

LinkedIn Optimization: Why do you need a strong LinkedIn profile?

Recruiters use LinkedIn as a key tool in looking for qualified job candidates. Our top goals in upgrading your LinkedIn profile are:

1. Ensuring that recruiters can find you using LinkedIn – LinkedIn search has numerous algorithms that it uses for the recruiting search. We want to make sure that your profile is found during this search.

2. Make your LinkedIn profile standout so that once you are found, potential employers will know that you are a top candidate for the position.

3. Communicate where you are in your career and what you are looking to do in the future (use your Headline and Summary/About section for this).

4. Grow your network and utilize your network to help in your job search.

LinkedIn Profile Picture

I don’t want you to spend a lot of time worrying about this – I know that this becomes a tough topic as we get into our 40s, 50s, and beyond.

My biggest advice for your profile picture is that you pick something that looks like you.

My profile picture was taken on an iPhone by my teenager in our backyard.

Some folks are moving towards the AI-generated pictures – those really aren’t my favorite (but that’s a personal preference – it’s not a hard and fast rule).

The picture should be of only you (not a group).

In the end, I want you to have a picture that you feel comfortable with and that represents you.

LinkedIn Banner

You can choose to add a customized banner to your profile. Canva (https://www.canva.com/linkedin-banners/templates/) has several free templates that you can use if you are interested in making one of your own. You could also choose a photograph of a location (or general picture) if you would like. Either way, I’d like to see you remove the blue banner as a way to show that you are current/up-to-date on LinkedIn best practices.

LinkedIn Connections

LinkedIn shows accounts with 500+ connections higher in search results, so it would be helpful for you to get to 500+ connections. You can reach out to past coworkers, past classmates, friends, and then try to make new connections with recruiters or others in your industry.

LinkedIn Headline

We’re going to use the same strategy that we used to create your resume headline.

Some folks like the:

“I drive growth for healthcare start-ups” or

“I deliver IT strategies for Fortune 500 leaders”

I’m OK with this if it fits with your overall search strategy.

But I don’t want you to be creative for the sake of being creative.

In the end, we want your headline to attract the right kind of attention (from recruiters, hiring managers, potential clients, etc).

I’m going to repeat what we talked about in forming our resume headline because those same concepts apply here.

Think about what sets you apart from the competition – these are the things that we want to emphasize in your headline and executive summary.

You can choose a general statement (i.e. Executive Leadership, Fortune 500 Leader).

You can also add in the top skills and keywords required for the role.

Sample phrases include:

• Fortune 500 HR leader

• VP, Procurement

• CMO Advisor

• Technology Transformation

• Award-Winning Sales Leader

• Multi-Million Dollar Projects

• M&A Expertise

• Army Veteran

• PMP Certification

• Community Board Leader (Do you volunteer in your community? If so, highlight this!)

Then, put it all together for a catchy headline:

Fortune 500 HR Leader | Army Veteran | Multi-Million Dollar Projects | Community Leader

I deliver healthcare transformation for world-class hospitals | Award-Winning VP | Board Advisor

VP, Business Operations & Strategy | Fortune 50 Executive

Vice President, Real Estate & Facilities | Fortune 500 | Industry Board Leader

Director, Strategic Marketing | CMO Advisor | Award-Winning Revenue Growth

LinkedIn About Section:

You are limited to 2600 characters in your About section and we want to use that space to show your value proposition to potential employers. The trend right now is to write your About section in 1^st person, but really I am fine with either 1^st person or 3^rd person as long as you have a clear value proposition.

The About section previews the 1^st three lines of your summary, so we really want to catch the reader’s eye with the introduction. A recent study shows that only 3% of profile viewers actually click through the About section, so you want to write something compelling that prompts the reader to want to read more.

There are 2 different ways that I like to start my About sections.

Version 1: Mission statement or value proposition

Use your opening statement to show how you can deliver value to future employers.

My mission is to drive multi-million dollar sales growth for world-class SaaS start-ups.

My mission is to optimize spend for Fortune 1000 companies.

My mission is to build high-performing marketing organizations for top global chemical companies.

Version 2: Lead with your title and/or name drop your past experience

If you have strong experience, it may make sense to lead with that in your introduction.

As an award-winning Marketing Executive, published author, and widely-sought speaker, I have built a career jumpstarting growth for Fortune 500 retailers including The Gap.

Throughout my career with award-winning start-ups, world-class technology companies, and Fortune 500 leaders, I have consistently launched cutting-edge products and services to drive growth.

In roles including VP of Procurement for GE, I made it my mission to optimize our supply chain processes and cut costs while ensuring supplier quality.

Once you put together a compelling opening statement, you can use the rest of your About section to tell your story. Some folks prefer to be brief, others prefer to use as many of the 2600 characters allowed as they can. Use the highlights from your resume (executive summary and experience) as a starting point. You don’t have to go crazy here – you just need to give enough detail so that recruiters can find you when they are search from appropriate candidates.

LinkedIn Experience Section

You can use your experience from your resume in LinkedIn.

Some folks will tell you not to copy/paste your resume experience into LinkedIn – I am ok with that as a start. Our goal is to use your profile to attract attention, so if there is specific experience that you would like to emphasize, I would do that.

I understand that sometimes results are proprietary, so I’m fine with not including specific numbers and results in LinkedIn (although if you can provide numbers, that would be great).

You have 2000 characters to share your biggest highlights. What I recommend: rewrite your role description from your resume in 1^st person and then share your biggest role highlights in bullet form.

Linkedin Education Section

This is pretty straightforward. You can include all of your college coursework here.

You should not include years of graduation or GPA.

If you completed any continuing education coursework at any college, I would include it here.

You can reorder education if you would like (let’s say you want your Bachelor’s degree to show before your Masters’ degree) by choosing the reorder button.

How to counter and troubleshoot common job search issues for Gen X/Baby Boomer job seekers

Problem 1: Coming back from a career break

62% of Americans have had a career break

You don’t have to discuss health issues or the personal reasons why you took a break

You can discuss a layoff (but stay positive)

Try to stay current during your break

• Consulting projects

• Volunteer work

• Coursework

Use a career note to discuss on resume

Problem 2: How do you come back from “underemployment” or a “career step-back”

• Emphasize past experience that aligns with career goals

• Show this experience in your executive summary/About sections

• Be clear in your interview

• Acknowledge that you took an “in-between” role in order to pay the bills

• Stay positive

Problem 3: You’re “overqualified”

1. Lean into your expertise

You want to demonstrate how you can step in and quickly make a difference.

How can you solve the company's pressing issues?

How have you delivered results in the past?

Here's what to say:

"Yes, I have been doing this work for many years and I can quickly step in and deliver results. For example, when I worked for XYZ Corp, I increased sales by 50% in 18 months through building awareness via social media."

2. Acknowledge if you are looking to step back

Some of my clients have been in leadership roles, but are looking to move back into an individual contributor role

Here's what to say:

"I've succeeded in individual contributor roles throughout my career. I understand that XYZ Corp is looking to expand into the direct-to-consumer marketplace. Let me tell you how I have done that work in the past."

3. Counter the "you'll be bored" argument

How can you really be bored at work if you are contributing to the bottom-line?

That's right - you won't be.

Here's what to say:

"That's interesting that you would say that. I've never been bored in roles where I am contributing to the growth of a company. I know that XYZ Corp is looking to grow its online presence - here's how I can help."

Problem 4: Salary is too low

Make sure that you are applying for the right roles and revisit salary expectations:things aren’t where they were in 2021. Also, make sure to do some salary benchmarking on Salary.com and Glassdoor.

Final Thoughts

I know how discouraging today's job market can feel—especially for experienced professionals who have spent decades building successful careers. My hope is that this guide gives you practical strategies, renewed confidence, and a reminder that your experience is still incredibly valuable. The goal isn't to hide your career; it's to position it in a way that helps employers quickly understand the value you bring.

Ageless Careers Toolkit

This guide was taken from the materials in the Ageless Careers Toolkit, which was designed to give everyone access to my best practices in job search, resume writing, LinkedIn profiles, cover letters, and interviewing.

I'm committed to helping you become more visible and find a new role, so I'm offering this program for $29 (use the coupon code NEWJOB2026 at checkout).

What’s inside:

5 practical, on-demand modules with written guides, examples, and videos:

• Build Your Ageless Career – job search strategy and common pitfalls
• Write Your Ageless Resume – how to position experience at any stage
• Create Your Ageless LinkedIn Presence – so opportunities can find you
• Craft Your Ageless Cover Letter – clear, efficient, and effective
• The Art of Ageless Interviewing – confidence and preparation

I also cover issues I see every week in my practice, including:

• how to show early-career experience (yes, even from the 80s or 90s)
• how to explain career breaks or step-backs
• what to do if you’re not getting interviews

If you’ve been feeling stuck or unsure about your next move, I made the Ageless Careers Toolkit for you.