A staffing agency sells candidates. A boutique executive search firm sells one outcome: a named senior person in a seat in four months. The client is almost never the HR department. It is a CEO, a board chair or a founder with an open chair that is costing the company money every week, and your first message has to read like it came from someone who already understands that chair.
The way in is a one-page search outline sent before the client has hired anyone. This guide covers how to spot the opening early, what goes on that page, and how retained terms differ from the contingency work most recruiters know.
Retained or contingency: choose before you write
In contingency recruiting you are paid only if your candidate is hired, and the client can work with many recruiters at once. In retained search, the client pays an agreed fee in installments and gives you the search exclusively for a period. The retained model fits roles where the client wants a researched shortlist and where the miss is expensive: a CEO, a CFO, a head of sales. Fees in retained search are commonly set around a third of the first year's cash compensation, paid in three installments. Terms vary, so treat that as a rule of thumb and set your own.
A rule of thumb for fit: if the client would hire the first decent candidate from a job post, it is a contingency role. If they need someone found who is not looking, it is retained. Don't mix the two in one email. The offer for each is different, and we cover the staffing side in getting staffing agency clients and the middle ground in getting clients as a recruiter.
Spotting the opening before the posting
By the time a senior role is posted, three recruiters have called. Look for earlier signals. A departing executive often appears in a company press release or on the executive's own profile. For public companies, an 8-K filing under Item 5.02 reports the departure of a director or officer, and the SEC's EDGAR database is free and searchable. For private companies, follow funding announcements: a company that closes a Series B often needs a head of sales, a CFO or a VP of engineering within six months. Other signals: an acquisition, a new board member, a founder moving to a chair role, a growing team with nobody in charge of it.
Who to write to
Write to the person who will make the hire, not the one who will manage the process. For a senior role at a company with under a few hundred people, that is the CEO or the board chair. For a non-executive search, such as a director-level finance role, it is the head of HR or the executive who will manage the hire. Build a list of 30 companies with recent signals, with the decision maker named for each, using how to find decision makers at a company and how to get meetings with decision makers.
The one-page search outline
The outline is your first offer, and it takes about 90 minutes to write for each company. It has five parts: the role and why it matters now, the profile you would target (the kind of company the person comes from, the scale they've run, the two or three things they must have done), five to eight companies where you'd look, a realistic timeline, and the fee and terms. Because you've done real homework, the CEO sees you already know the market. They don't need to hire you to benefit from the page, which is exactly why they'll read it.
An illustrative example. A 90-person medical device company has just raised $30 million. Its CEO, Rosalind Teague, has a founder running sales and no VP. Your outline proposes a VP of Sales with hospital capital-equipment experience, names the kinds of competitors and adjacent firms to search, and projects a 14-week search. The role pays $220,000 in cash compensation, so a 33 percent fee comes to $72,600, paid in three installments of $24,200. You state a 90-day exclusivity period and a replacement if the hire leaves in the first year, if that matches your terms.
A first email to a CEO
Subject: Your VP of Sales search, a one-page outline
Rosalind, congratulations on the Series B. A company at your stage with sales still run by the founder usually looks for a first VP of Sales within the next two quarters. I run a small retained search firm that places commercial leaders at medical device companies. I wrote a one-page outline of how I'd run that search for you: the profile, where I'd look, and a realistic 14-week timeline. May I send it? No obligation.
Cassian Moore, Moore Search Partners, 5 Harbor Plaza
Include your physical address and an opt-out, as CAN-SPAM requires. The client in a regulated industry should also check your confidentiality terms; promise discretion and keep it.
Following up with a market view
If the CEO doesn't answer, don't ask again. Send something new: a short note saying what you've seen in the market for that role, like how many strong candidates are reachable at the moment and what they're being offered. This builds trust without pressure. Send one every four to six weeks to your list of 30. See following up with a lead who said not now for the pacing.
Fee terms and exclusivity
Ask for exclusivity for a fixed period, commonly 60 to 120 days, and explain why: you can't recruit hard for a role that three other firms are chasing. Be flexible on installments and firm on exclusivity. A client who wants ten firms on the same search is a contingency client, so offer contingency terms or decline. Write your terms in a short engagement letter, and have your own lawyer review it. Employment agency licensing rules vary by state, so check yours.
Ten emails with real homework in them beat a hundred form letters. Rocketship can track the signals, find the CEOs by name and send the outline offer from your own Gmail, with follow-ups on a schedule; see how the AI workers run it. The partner-first approach in the R&D tax credit guide is a useful contrast: a specialist who sells through an intermediary instead of straight to the CEO.
Rocketship finds the buyers, emails them from your own Gmail, follows up, and books the meeting on its own. Plans that get you customers start at $24.99 a month (Launch), and both Launch and Frontier start with a 7-day free trial, card required.