PeakPitch Executive Search · Finance Leadership
A finance leadership hire isn’t a role you fill. It’s a decision you live with for years — in your monthly close, your board meetings, your ability to raise capital or sell the company when the moment comes. Get it right and most of what follows gets easier. Get it wrong and you keep paying long after the search is forgotten.
Two decisions shape how it goes: who you trust to run the search, and how you reach the people who would never answer a job post. We’ll take them in that order.
First, who you hand the search to
Choosing a firm means choosing who represents your company to the leaders you’re trying to hire, and who’s on the hook when it’s done. The name on the door tells you less than you’d think. Ten questions tell you almost everything.
1. Who’s actually doing the work?
At many large firms, the person who wins you over in the pitch isn’t the person who runs your search. They hand it to a consultant you’ve never met. Ask, plainly, who does the day-to-day recruiting — and make sure it’s the same person sitting across from you now.
PeakPitch: Peter Nelson pitches your search and runs it himself. The person you meet is the person doing the recruiting, from first call to final offer — there’s no handoff.
2. Retained or contingent?
Retained fits senior, confidential, can’t-afford-to-miss roles. Contingent can make sense for higher-volume hiring with a deep pool of active candidates. Pick the model that matches the stakes, not the one with the smaller invoice. For a fuller comparison, see retained vs. contingent search.
PeakPitch: We work exclusively on a retained basis, so a senior finance search gets a dedicated, committed process instead of a race to submit résumés.
3. Have they done this exact kind of search?
A first-time CFO for a founder, a CFO steering toward a sale, and a controller cleaning up the books are three different hires. Ask for placements that look like yours — same function, same stage, same ownership.
PeakPitch: We focus only on finance and accounting leadership — CFOs, CAOs, controllers, and VPs of Finance — for middle-market and investor-backed companies, so your search sits squarely in our lane.
4. How full is their plate?
A recruiter carrying a dozen searches can’t give yours real attention. Fewer searches means more hours on yours and a sharper shortlist.
PeakPitch: We keep our caseload deliberately small, which means real hours and senior attention on your search rather than a spot in a long queue.
5. Who’s off-limits?
Retained firms can’t recruit from their own clients for a stretch. At a large firm with a long client list, that quietly walls off some of the best candidates — a tradeoff we dig into in boutique retained search vs. the SHREK firms. Ask for the off-limits list for your search before you sign anything.
PeakPitch: As a boutique with a narrow client base, we carry fewer conflicts — and we check off-limits against your specific target list before we begin.
6. How do they judge a candidate?
You want a method, not a stack of forwarded profiles — real interviews, a defined profile to measure against, and references someone actually called.
PeakPitch: Every candidate completes a detailed first-round interview with us and reaches you with a written dossier making the case for fit, not just a forwarded résumé.
7. How often will you hear from them?
Ask about cadence. Regular updates with honest market feedback let you adjust early, instead of learning at the finish line that the profile was off. It’s a big part of what to expect when you engage a retained search firm.
PeakPitch: You get a weekly progress update built around a clear search matrix, so you always know exactly where things stand.
8. Can they keep it quiet?
If you’re replacing someone or heading into a transaction, discretion isn’t optional. Understand exactly how they protect your name and the opportunity.
PeakPitch: We run confidential, targeted searches, so sensitive transitions stay discreet from the first outreach.
9. What happens if it doesn’t work out?
Good firms stand behind a placement with a replacement guarantee inside a defined window. Get it in writing.
PeakPitch: We stand behind our placements and set clear guarantee terms up front, in writing.
10. Will they let you call their clients?
Talk to people who’ve hired them for something like your search. Their experience is the best predictor of yours.
PeakPitch: We’re glad to connect you with clients we’ve placed finance leaders for — our references are the pitch.
The warning signs
- The pitch team and the delivery team aren’t the same people.
- Vague answers about caseload, off-limits, or how candidates get assessed.
- Pressure to move fast, non-exclusive and pay-on-placement, for a senior role.
- No clear reporting rhythm and no replacement guarantee.
Then, who you’re really trying to reach
Here’s the part most companies get backwards. You post the role, you wait, and you interview whoever turns up. The trouble is that the person you actually want almost never turns up.
The people you want aren’t looking
The best CFOs and controllers are already in seats, already delivering, and not thinking about job boards for a second. They’re passive — open to the right move if it finds them and arrives with credibility, invisible to a posting otherwise. Advertise the role and you reach the people who happen to be available. That’s a very different group from the people who are good at the job.
Why a job post misses them
- Postings surface active seekers, which skews away from top performers in stable, high-impact seats.
- You can’t advertise a sensitive change — replacing an incumbent, prepping for a deal — without tipping your hand.
- A senior posting draws a pile of unqualified applications that eat time and improve nothing.
- A résumé won’t tell you whether someone has actually done it in your ownership model, at your stage, on your systems.
The best hire is rarely the best of who applied. It’s the right leader who was never going to apply in the first place.
What it takes to reach them
Reaching passive leaders is research, not advertising. You define the hire in detail, map the market to find the handful of people who genuinely fit, then reach them directly and quietly — with enough credibility to earn a conversation from someone who wasn’t looking. That’s the whole point of a retained search.
How we find the ones you can’t
This is the work we do. We build the success profile with you, map the market, and go straight to the finance leaders who match — including the ones who’d never reply to a posting. Every candidate has already sat through a real first-round interview before you meet them, and arrives with a written case for why they fit your role, your culture, and your goals. You get a weekly update the entire way. And because Peter runs the search himself, the outreach comes from someone a serious CFO will actually take a call from.
The questions we hear most
How do you choose an executive search firm?
Look past the brand to the person who’ll actually run the search, their track record in this kind of role, their caseload, how they assess candidates, their off-limits list, their reporting cadence, and their guarantee. Accountability lives with the people doing the work.
PeakPitch: You work directly with Peter Nelson from the first conversation through placement — no sales-to-delivery handoff.
What questions should you ask an executive search firm?
Ask who does the day-to-day work, how many similar searches they’re carrying, which companies are off-limits, how candidates get assessed beyond the résumé, what reporting you’ll get, and what the replacement guarantee is.
PeakPitch: We welcome every one of these and answer them in writing before an engagement starts.
What’s the difference between retained and contingent search?
Retained is exclusive and paid in stages for the process, built for senior and confidential roles. Contingent is paid only on placement, often non-exclusive, and better suited to higher-volume hiring.
PeakPitch: Every finance search we run is retained, which is what makes proactive outreach and real assessment possible.
How do you recruit a CFO?
You define what the role has to deliver, map the market of qualified leaders, and reach them directly and confidentially — not post and wait. Then you judge them against your ownership model, stage, and goals, not just their résumé.
PeakPitch: We run a proactive, retained search that reaches the strongest finance leaders, most of whom aren’t looking.
What is a passive candidate?
Someone who’s employed and not job-hunting, but would consider the right move if approached. The best senior finance leaders are almost always passive, which is why a posting won’t reach them.
PeakPitch: Going straight to passive candidates is the heart of what a retained boutique does.
When should a company hire a CFO?
Usually when growth accelerates, a financing or transaction is on the horizon, the finance function needs to grow up, or a sale or succession is coming. The right time is before the gap in financial leadership starts holding the business back.
PeakPitch: We help you pin down the finance leadership your moment calls for — first-time CFO, sponsor-facing CFO, or beyond.
Related reading
- Retained vs. Contingent Executive Search
- What to Expect When You Engage a Retained Search Firm
- Boutique Retained Search vs. the SHREK Firms
- How Much Does a Retained Executive Search Cost?
Planning a senior finance leadership hire?
Talk through the search and the right candidates with Peter Nelson at peak-pitch.com.
PeakPitch Executive Search — boutique retained search for finance and accounting leadership across the Western and Central U.S.
