Why Many Small Business CEOs Fail At Job Search

Have you had enough of being a CEO of a small business?

(Maybe your official title is not CEO – it’s probably MD, GM or similar – but in this article I’ll use CEO as an umbrella term for all of those to aid consistency and comprehension).

Often the pressures of running a small business to small business CEOs and they begin to dream of having a “normal” job.

At least for a little while.

CEO job search

However, getting a job after being a small business CEO is not always easy.

Press any recruiter and they’ll (grudgingly) admit that CEOs who have been running their own business for the past 10+ years often get overlooked during job search.


Recruiters like to fit square pegs into square boxes. They don’t get paid to take big risks. And you, somewhat unfortunately, are a round peg.

You may have built a business and have more business experience than an entire Ivy League MBA class combined, but that won’t necessarily help you during job search.

It means you need to play a shrewd game. Which is what this article is all about. Read on to win at job search after a long stint as a small business CEO.

Problem 1: You’re Not Communicating Your Strengths

There’s a simple reason there’s a huge market for resume writers: most people aren’t very good at communicating their strengths on their resume.

As someone with experience in both executive recruitment and resume writing, I can confidently say this is the top reason why small business CEOs get overlooked by recruiters.

Truth is, your strengths are numerous. As a small business CEO you’ve had to wear many hats – from marketer to customer service representative to debt collector.

However, positioning yourself as a jack-of-all-trades on your resume will make your job search considerably more difficult.

You need to communicate your value with razor-sharp focus, perfectly aligned to your intended direction.

You also need to show what makes you unique, why you do what you do, and what you’re like to work with.

Problem 2: You’re High Risk

Senior hires present a considerable risk for companies, and it is the recruiter’s responsibility to minimise that risk.

While it may feel like a recruiter is on your side, their focus is their client – hence they’re assessing your motivation, commitment, and all the variables that could derail your candidacy.

When a recruiter calls to follow up on your application, it’s critical you work to allay their unspoken concerns.

For example, relocation is one of the most common – and significant – risk flags, especially if you will bring a partner or children with you.

In your initial call with the recruiter, demonstrate that you’ve thought through the potential move; mention that you’ve looked into the real estate market, job market and schools for your family.

Having a rough plan in place to manage the transition signals you’re serious.

Problem 3: Your Salary Expectation Is Unrealistic

Salary is the other top risk, and recruiters will use information about your current salary as a mitigation strategy.

If you’re currently making $200k as a CEO of your own business and the client’s budget is $150k, it’s a red flag.

While a recruiter won’t share their client’s budget with you, they will work to manage the risk by asking subtle questions about what’s important to you.

Answer honestly to help the recruiter understand how big of a deal (breaker) salary is, and how open you are to other forms of compensation, like vacation time, telecommuting, and benefits.

CEO resume

Problem 4: Your Resume Is Confusing

Recruitment is a high volume industry, and recruiters are expected to juggle multiple projects, racing against internal and client deadlines to move the process along as quickly and efficiently as possible.

With that in mind, one of the worst things you can do is make it difficult for recruiters to find the information they need with a resume that is:

  • disorganised,

  • too long

  • too short

  • containing irrelevant information (leaving it to the recruiter to connect the dots)

  • poorly written.

Use a traditional, reverse chronological format resume – unless you have strong rationale for doing otherwise.

(Functional resumes – where you list job titles and companies without detailing specifics, and then group duties and accomplishments together without specifying the ‘where’ and ‘when’ – are the bane of most recruiters’ existence).

Because you’re a small business CEO, you’ll be considered “one of those people” who has a non-traditional background.

It means you’ll need to make an effort to highlight transferable skills on your resume.

If your work history is very complex, I recommend that you work with a professional resume writer to help you present your experience in a way that is easy for recruiters to understand (How to choose the best resume writer?).

It’s also important to keep your resume structurally organised, to the point, and relatively short – though detailed enough to convey your overarching message.

While Australian and UK resumes tend to be longer than resumes written for the USA job market, concise and precise language is expected everywhere.

Stick to a maximum of 2-4 pages (depending upon the country in which you’ll be applying), using the first page to create a persuasive professional profile, as well as an executive career summary, key skills and qualifications.

Populate the middle pages of your resume with role descriptions and accomplishments in reverse chronological order, and the final portion of the last page can be reserved for non-critical, but relevant information such as technical skills, presentations or publications, honours and awards, and volunteer positions.

5. You Are Difficult To Find Online.

Consider this: many recruitment firms don’t advertise the positions they’re contracted to fill.

Instead, they prefer to actively source candidates through internal databases and online platforms.

If your job search strategy consists of reactively applying to posts on job aggregator sites, you’re likely missing out – especially at the management and executive level.

Start by embracing LinkedIn and fixing your LinkedIn profile.

It’s the first place most recruiters go to search for candidates online, and it’s more important than ever to have a robust profile that uses appropriate keywords, includes a professional headshot, and highlights the value you bring to an organisation.

While LinkedIn is a good place to start, don’t stop there.

Increase your online footprint by investing in a personal domain name, and populate it with a combination of personally-branded storytelling that communicates your unique selling proposition (USP), along with blog posts that share your insights into key challenges and opportunities facing your function or industry.

Saying you’re a thought leader isn’t enough anymore: you need to actually demonstrate it.


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