How to Write the Best Cover Letter for Executive Job Search

I’ve written many times here about why you should always include a cover letter or cover email when you send your resume to various people.

And I’ve written about what the experts say about cover letters.

Cover letters really do matter.

How to Write the Best Cover Letter for Executive Job Search

Cover letters vary in content and length, depending upon the recipient:

• Job application letter (responding to a job posting on a job board or company website)
• Networking letter (used to network your way into the goldmine of hidden executive jobs)
• Prospecting letter (send to recruiters, HR and others at your target companies)
• Career change letter (may be used to respond to job postings or to reach out to your network)

I’ll include examples below, but the basic structure of a cover letter is usually the same:

Salutation

Address a real person, as in “Dear Ms. Smith”. Using “Dear Sir or Madam” won’t cut it, and will indicate to the reader that you were lazy or didn’t care enough to find someone to write to.

First paragraph

Introduce yourself and why you’re writing to them. If written well, the first few sentences will capture attention and compel people to want to read further.

There are various ways to approach this. You can start with an intriguing question or a bold statement. You’ll see examples below.

Second through (perhaps) fourth or fifth paragraphs

Include a rundown of your relevant skills and experience, with specific examples of wins for past employers that will resonate with potential employers, whenever possible. If you’re using a job description, be sure your cover letter includes plenty of the keywords and phrases that you find in it.

If you have no job description to work from, do some research on the companies and industry, and talk to people who work at the companies or are associated in some way. For instance, you can request an informational interview.

Final paragraph

Wrap it up in one or two sentences. Thank them for their consideration and express interest in speaking with them about what you have to offer.

Important tips as you write your cover letters

Remember that the purpose of your cover letter/email is to be even more specific than your resume.

Don’t rehash what you already put in your resume. This is your opportunity to provide more info about yourself.

It’s meant to address specific achievements and contributions of yours that will resonate with that particular recipient.

You may be able to re-use some of the content in the middle paragraphs verbatim for several of your letters. But make sure the info really applies to that recipient, and the qualifications needed for the job and company.

If the best you can do is send the same generic cover letter to every recruiter and employer hiring authority, assuming they will somehow interpret your good fit from your unfocused mishmash, don’t bother.

A generic letter does nothing to differentiate how you’re uniquely qualified for the job.

Being generic in your cover letter positions you as the same as other candidates. How does that help anyone determine that you’re a standout who needs to be considered?

People will easily spot a generic letter and probably disregard you. You’ll come off as not willing to take the time to personalize your letter.

Generic letters are a problem because they don’t contain specifics about how you will help that particular employer.

Because a cover letter is more specific than a resume, it affords the opportunity to position yourself not only as the right fit for the job, but also the right fit for the company.

And cover letters are where you will address employment gaps or other potential red flags in your resume, plus things like whether you’re open to relocation or why you’re making a career change.

One little-used cover letter tactic

One way you can stand out in your cover letters while backing up the claims you’ve made in your letter and resume is to include relevant, hard-hitting accolades from people you work with.

The way you’re perceived by others is one of the best ways to communicate your personal brand and get some of your personality into the letter.

I also often include accolades in resumes, but I don’t use the same ones in the cover letter.

Here’s an example of a glowing accolade I put in one client’s cover letter. He’s the same senior healthcare generalist noted in the examples below:

“Tom works well with all people and seeks to understand all sides of a situation. His work is governed by the highest of ethical standards, moral values, and commitment to transparency through honesty. He constantly demonstrates a productive sense of humility and the one quality I constantly seek in a leader, which is to know when you do not have the necessary command of knowledge about a subject, and to take measure(s) to rectify that by asking the appropriate question(s) or educating yourself before speaking.”

What about formatting for your cover letter?

Since your letter is likely to be read on a phone or small-screened device, make sure you include plenty of white space for ease in reading, and to draw the eye down the page.

Using subheadings is another good way to break up content and highlight your value-add.

But avoid using enhancements (like images and special fonts) that may not “read” on the recipients end.

Overall, make sure you don’t make these 10 job search email mistakes.

Also understand that, when recruiters and other hiring professional are the recipient of your cover letter with resume, the cover letter will probably go into their Applicant Tracking System (ATS), along with your resume.

That means that both documents will be parsed for the various relevant keywords and phrases they have put into the system.

Here’s what happens to the documents:

• They’re put into a database or ATS, along with thousands of other people’s resumes and cover letters, for various kinds of jobs they’re trying to fill.
• The ATS attempts to match candidates to jobs. The database sifts through the documents and parses their content for matches to particular jobs.
• Candidates are selected if they meet the requisite qualifications.
• Candidates may not be selected if their documents are incorrectly formatted, or don’t contain enough of the right keywords, or the candidate doesn’t fit the bill in some other way.

Examples of cover letters

I’ve included these examples to help guide you in writing your own. Be aware that I wrote these for actual clients of mine, so these cover letters are probably in circulation.

Just like you wouldn’t copy someone else’s resume, you should not copy any of this content and use it in your own cover letters or elsewhere. Plagiarism is always a bad idea. It can come with disastrous consequences and is plain wrong to do.

Cover letter introductions

Here are a few examples of the first paragraph(s) of cover letters I wrote for clients.

This one is for a Chief Information Security Officer:

Many otherwise successful companies struggle to strengthen cybersecurity, often because their Chief Information Security Officer is not taking a more strategic enterprise role.

Why is this? Because most CISOs are technologists by training and trade . . . not business partners. My IS / IT expertise comes with keen business acumen, and a quickness to understand and deal with business risks and opportunities . . . resulting in optimized global enterprise technology capabilities. My business MBA specialization was in Project Management with a concentration in Marketing.

Cover letter intro for a Cybersecurity GRC – Information and Risk Management Specialist

Over the past 10 years or so I have been providing Cybersecurity GRC consulting services and leading Information Security and IT Management initiatives for various Fortune 500 companies, including finance organizations. I am up-to-date with industry-leading practices, global cybersecurity standards and the latest trends in GRC management. My expertise includes proactive leadership of Information Management, Regulatory Requirements, Third Party Risk Assessments and Data Classification.

And here’s one for a senior healthcare generalist:

I’m that proverbial “jack of all trades” consultant – a senior healthcare generalist with a multi-disciplinary background strengthened by 14 years’ experience in diverse environments in academia (exercise and sports science, biomechanics, physiotherapy, education faculties).

Full cover letter

Here’s the full networking/referral cover letter I wrote for a Corporate Turnaround Management Executive, with identifying information fictionalized to protect her confidential search.

Dear ——,

Mark Stewart suggested I contact you directly. I connected with Mark at the Association of Financial Professionals convention, where he mentioned you would be filling the COO spot in the next few months.

A change agent for companies in distress, I offer [company name] deep expertise in restructuring and turning around failing financial and operational performance to capture healthy, sustaining profitability and growth.

My value-add is powered by these core strengths:

Finance and Accounting Management – An unwavering numbers and metrics watcher, I have the dexterity to anticipate potential risk factors; establish a viable budget, financial model, and profit objectives; control P&L, cash flow, and asset management; preserve equity; and oversee mergers and acquisitions.

Leadership and Mobilization – Practiced at gaining the trust of my colleagues and managing by “walking around”, I know how to talk to people, develop a comfort level, and rally them around what needs to be done. Getting an accurate read on the pulse of the organization and connecting with employee views of operational opportunities and concerns are two keys to my management strategy. I raise the bar by focusing on results, not effort, and get everyone excited about the journey we’re all on together.

Organizational Structure Improvement – Doggedly persistent and proactive in the face of complex recovery obstacles, I challenge status quo processes, pursue strategic alternative approaches, and take calculated risks associated with evolution. My success lies in the innate ability to synthesize the functional areas of Engineering and Operations, Finance, Administration, HR, Legal, and Marketing and Sales.

Customer Relationship-Building – Driving an organization to act as if any customer service failure is intolerable, I make it easy and pleasant for them to do business with our company. I have a strategic talent for ensuring “fit” between products, clients, and markets.

I welcome the opportunity to meet with you to discuss my potential contributions to [company name]. Mark believes I’m a good fit for your company, and I look forward to exploring that potential. I’ll call you next week to discuss scheduling a meeting.

Thank you for your consideration.

Sincerely,

Susannah Moore
Enclosure: Resume