Writing to a CEO When There Is No Vacancy
Many senior roles are never advertised. Some are not even planned. They are created because the right person turned up at the right time.
That person is often someone who wrote to the CEO with a clear idea of a problem they could solve. Not a resume with a hopeful note. A short, sharp message that made the CEO think, “I should talk to this person.”
Most speculative letters fail. They are long, vague and all about the writer. A good one is the opposite. It is brief, specific and all about the reader’s business.
This article covers when a direct approach works, how to research the problem you can solve, the structure of a short letter, a full example message, following up and the mistakes that kill it.
When it works
A letter to a CEO is not a magic door. It works best in certain conditions:
Mid-sized and growing businesses. The CEO is close to the hiring decisions and can create a role quickly.
Private equity or founder-led businesses. Owners often move fast when they see someone who can fix a known gap.
Businesses going through change. A merger, a new market, a funding round, a new system or a turnaround. Change creates needs before job descriptions exist.
When you have a clear, relevant edge. You have solved this exact kind of problem before.
It works less well with very large listed groups, where hiring runs through formal processes and search firms. It also rarely works when your message could have been sent to any company.
For more on how unadvertised roles appear, read the hidden job market for executive roles.
Researching the problem you can solve
The research is the letter. Without it, you are just asking for a job.
Spend an hour or two on each target. Look at:
Annual reports, investor updates or the chair’s statement, if available
Media releases and news about growth, acquisitions or restructures
The CEO’s own LinkedIn posts and interviews
Job ads they have posted recently, which hint at gaps
Industry news that affects them, such as regulation or supply changes
Then answer one question: What is the most likely problem on this CEO’s desk that I have solved before?
Examples:
A business that has made three acquisitions in two years probably has messy reporting and systems.
A founder-led company that just took private equity funding probably needs board-ready reporting and stronger cash discipline.
A business expanding into New Zealand or Australia probably needs help with structure, tax and local banking.
Pick one problem. Not five. A focused letter beats a broad one every time.
Structure of a short letter
Keep it under 200 words. A CEO will give it about 30 seconds.
The hook. One or two sentences showing you understand something specific about their business.
The problem. Name the likely challenge plainly.
Your evidence. One or two results from your past that match it. Use numbers.
The ask. A short conversation, not a job.
The sign-off. Your name, title and contact details.
Attach nothing. Or, at most, a one-page summary. A full resume turns the message into an application, and the CEO will forward it to HR.
Example message
Here is a full example, written by a CFO to the CEO of a growing services business.
Subject: Integrating your three acquisitions
Dear Michael,
Congratulations on the acquisition of the Queensland business last month. That makes three in two years, which is a strong run.
In my experience, the third acquisition is often where reporting starts to strain. Different systems, different charts of accounts and month-end that takes longer each quarter.
I have dealt with this twice. As CFO of a national services group, I brought four acquired businesses onto one system and cut the monthly close from 12 days to 5. The board received one consistent set of numbers for the first time.
I am not writing about a specific role. I would value 20 minutes to hear how you are thinking about finance as the group grows, and to share what worked for us.
Would a call in the next two weeks suit?
Kind regards,
Sarah Bennett
Chief Financial Officer
0400 000 000
That is under 150 words. It is specific, it shows evidence and it asks for a conversation. It does not ask for a job, and it does not describe Sarah’s personality.
Sending it
Email usually works best. Find the CEO’s address through the company website, a mutual contact or a standard email format. A LinkedIn message can work as a backup, but it is easier to miss.
A warm introduction is even better. If you share a contact with the CEO, ask them to forward your note with one line of their own. “I worked with Sarah. Worth 20 minutes.” That line often does more than the letter.
Time it well. Avoid the week of a results announcement, a holiday period or the days after a big news story about the company.
Following up
Most CEOs will not reply to the first message. That is normal. They are busy, not uninterested.
Follow up once, about a week to ten days later. Keep it shorter than the first message:
“Hi Michael, I wanted to follow up on my note about integrating your recent acquisitions. Happy to work around your diary if a short call would be useful.”
If there is still no reply, leave it for a few months. Then send something useful, such as a relevant article or a short observation about their sector. No pressure. Just a reason to stay on their radar.
Do not follow up more than twice in a short period. Persistence becomes pressure fast at this level.
Mistakes that kill it
Writing about yourself first. The opening line should be about their business, not your career.
Being vague. “I can add value” means nothing. Name the problem and your result.
Asking for a job. It forces a yes or no. A conversation is an easier yes.
Attaching a long resume. It gets forwarded to HR and lost.
Sending the same letter to 30 companies. CEOs can tell. It reads like a mail-out.
Criticising the business. “Your reporting is clearly a mess” will end the conversation. Frame the issue as common, not as their failure.
Getting the name or facts wrong. Check every detail twice.
How search consultants see it
When I worked in executive search, some of my assignments started because a CEO had met someone interesting. They had a conversation, saw a gap more clearly and then called a search firm to run a proper process. Sometimes the person who sparked it was hired. Sometimes they were not, but they were the benchmark.
Either way, the person who wrote first shaped the role. That is a strong position to be in. The letters that led to those conversations were short and specific. I never heard of a long, general one doing the same.
How many to send
Quality beats volume. Five well-researched letters will usually achieve more than fifty generic ones. Choose businesses where your experience fits a likely problem, then do the work on each.
Track who you wrote to, when, and what you said. A simple spreadsheet is enough.
Preparing for the reply
If the CEO says yes, be ready. Prepare a short version of your story, two or three questions about their plans, and one or two ideas that show how you think. Treat it as a conversation, not an interview. You are exploring a problem together.
For broader advice on building senior conversations, see networking for senior finance professionals.
A quick self-check
Can I name the one problem I could solve for this business?
Do I have a result with numbers that matches it?
Is my message under 200 words?
Am I asking for a conversation, not a job?
Your next step
Choose three businesses where your experience fits a likely problem. Spend an hour researching each, then write one short letter using the structure above.
If you want help with a direct approach strategy, my executive career transition support helps senior leaders open conversations that lead to unadvertised roles.
If you want a second view on your target list or your letter, book a complimentary Clarity Session.
