Olivia Gamber – Career Upgrade Roadmap

Occupational Olivia Gamber

Olivia Gamber is the founder of OccupationalOlivia.com where she strives to develop people to maximize their potential at work.

In addition to running Occupational Olivia, she also holds down a full-time job as the head of Talent and Organizational Development at with current company.

Because of her position, Olivia knows all too well that being good at your job isn’t enough in today’s highly competitive environment.

You must also be able to build relationships, navigate complex corporate matrices and develop many other key skills.

Olivia is the host of the Occupational Olivia podcast, which you can find on iTunes and Stitcher and she the author of the book “Career Upgrade Roadmap, 90 days to a better job and a better life”.

The book is a #1 best-seller in 3 categories on Amazon including job hunting, career development, and vocational guidance.

Olivia also offers a Career Breakthrough course and Coaching services.


After spending many years in the Human Resources department learning how recruiting and candidate sourcing really works, Olivia decided to start her website, occupational Olivia, as a way for her to share her thoughts and knowledge with others.

Prior to launching the website, she did have a conversation with her boss about the site and her intentions with it. The conversation was an easy one and Olivia was able to move forward.

Because she decided to just start, Olivia was able to vet out her thoughts and ideas online and people began to take notice.

As she was building her brand, Olivia began to attract an audience hungry for her content and information. This inspired her to launch her podcast, Occupational Olivia and eventually her book The Career Upgrade Roadmap.


As a full-time human resources professional, Olivia Gamber watched as the rules of recruiting started to change. The way recruiters were searching for candidates and the way the “A” type candidates were finding job openings had become dramatically different.

Olivia captured everything she was learning and shares it all in her book.

Olivia identified five steps or phases in the “new” job search process. She goes into detail about each one in the book that comes with an accompanying workbook so job seekers can execute the process as they read the book.

Olivia wrote the book with the following “types” of business professionals.

  • Underemployed
  • Highly Educated (bachelors, Masters Degrees)
  • Not being challenged
  • Not happy with their career
  • Feel stuck and don’t know how to move forward

If any of these descriptions fit with where you find yourself today, I highly recommend you check out Olivia’s book and get started executing the five steps.

I’ve provided a high-level overview of the steps here.


Olivia states right up front, this initial step of target identification, is the step that most people she speaks with skip.

The Career Upgrade Roadmap is unlike any job search process you may have grown up following. The “old school” job search method simply has you sending out your resume to multiple companies.

This may make you feel like you are getting a lot of work done but in reality, you’re just wasting your time. This is not how you get a job in today’s environment so do NOT skip this step.

Olivia challenges instead that the first step you need to take today is to identify the job titles and companies. Why job titles and companies? To help you become laser focused on what you want from your job search.

She recommends using LinkedIn to identify the job titles you feel you would like and can actually get with your skills and experiences. Olivia Gamber suggests you find 3 to 5 job titles to review.

Once you have the job titles, the next step in this process is to identify the 3 to 5 companies as well.

Step one is really conducting the research you’ll need to move into the remaining steps. You’ll spend a lot of time behind the computer identifying your target job titles and companies.

In step two, we’ll move away from the computer and into the marketplace.


Step two of the Career Upgrade Roadmap, market validation, can be summed up with one word, networking. Specifically, you will be identifying and meeting with individuals who have either held the job titles you identified in step one or who work for one of your target companies.

We are not applying for any positions in this step.

Step two is all about obtaining more information about the jobs you identified and the company. To do that you’ll use LinkedIn once again to identify individuals holding the job titles you identified or who work at your target companies.

Once you have this list of people, you will reach out to them and have a conversation. Your goal during this chat is to figure out if you will like the job and if you can actually get the job.

Olivia Gamer suggests reaching out to these individuals and if possible, asking them out for a cup of coffee. Remember your goal is not to ask for or apply for a job. Your goal instead is to learn.

While you are validating your target market you are also making connections and building your network. These are two key tenants to finding a job today.

Olivia and I discuss in detail how to structure these meetings and even provides a script for them in her workbook. If additional help is needed, Olivia is also available for coaching.


At the beginning of step three, you should have a very good idea of the job you want to pursue and can actually get. You may also have a few additional company names for further investigation.

Step three of the Career Upgrade Roadmap is all about maintaining the connections you made in step two. You do this through follow-up.

You may remember from my discussion with David Fisher, that follow-up may seem easy, most people will skip this step. Don’t skip this step.

Follow-up begins shortly after the meeting with you held with the individuals identified in step two, with something as simple as an email. A quick thank you email for their time and sharing their knowledge can go a long way.

But this is only the beginning. Additionally, you will be following up with them in order to keep them abreast of your job search progress. This will help you stay top of mind for them.

Olivia Gamber tells us to not be surprised during this step if you start to see opportunities being floated to you from the individuals you met with in step two.

Remember, we have still not yet applied for a position.

The opportunities that may come your way in this step is because you are maintaining a consistent connection with your network. Again, the companion workbook has worksheets and scripts for how to properly follow-up.


Your career narrative starts with your marketing documents, the cover letter, and resume. Yes, Olivia refers to these common job search documents as marketing documents.

This makes perfect sense if you really think about what a marketing document is supposed to accomplish, which is capturing the attention of those who review it.

Olivia and I spend quite a bit of time discussing the difference between a career narrative and what is typically put on a resume.

Building a narrative allows your resume to float the top of the stack, by showing how you can solve specific problems for specific companies.

You will do this by incorporating the information you learned about the job and company during your meetings in step two.

I think it’s important to point out that even here in step four we still have not applied for a job.


Ok. This is it. Step five is where everything comes together and we can apply for a job. However, we are not going to apply via the online application front door if you will.

Instead, we will be going directly to the hiring manager. All of our work up to this point has really served to raise our visibility and grow our influence with our target jobs and companies.

It’s highly possible that by the time we reach this step, hiring managers are already reaching out to us. If not, we’re reaching back out to the individuals we’ve already spoken in and remained in contact with throughout the process to ask for introductions to the hiring managers.

Because we are no longer an unknown commodity to them these individuals will more than likely take us directly to the people who make the decisions.


The Best ways to get in touch with Olivia can be found below.

Twitter: @theoliviagamber

Web: occupationalolivia.com

Podcast: Occupational Olivia Podcast

Course: Career Breakthrough course and Coaching services.

About The Author

Ryan Rhoten

I help you build your brand so you can grow your influence and get recognized for your expertise.