Blog | Executive Search Insights

You’ve Tried Recruiters Before. It Didn’t Go Well.

If you’re the owner of a growing business and you’ve hired a recruiter for a senior role, there’s a decent chance the experience left you frustrated. Resumes that didn’t fit. Candidates who disappeared. A process that felt transactional when the stakes were anything but.

You’re not imagining things. The model most business owners have been exposed to, contingency recruiting, was never designed for executive-level hires in owner-operated companies. It was built for volume, speed, and placement fees. And when you apply that model to a role that will define the next chapter of your business, it breaks.

This post breaks down the real differences between retained search and contingency recruiting, explains why the distinction matters for your next leadership hire, and helps you decide which approach fits your situation.

How Contingency Recruiting Works (and Where It Falls Short)

Contingency recruiters get paid only when a candidate is hired. That sounds like a good deal. You don’t pay unless you get results. But the incentive structure creates problems that aren’t immediately obvious.

Because they only earn when someone is placed, contingency firms are incentivized to move fast and present volume. They’re working multiple openings simultaneously, often across dozens of clients, and their primary goal is to get a hire across the finish line before another firm does.

What this means for your search:

Candidates are often sourced from job boards and active applicant pools, not passive, high-performing leaders who aren’t looking
The recruiter has limited time to deeply understand your culture, team dynamics, or the nuances of the role
You may receive a high volume of resumes, but few that reflect real alignment with your business
There’s no exclusivity. The same candidates may be submitted to multiple companies simultaneously

For mid-level or functional hires, contingency recruiting can work fine. But for a President, COO, or Integrator in a founder-led company? The model simply wasn’t built for that level of complexity.

How Retained Executive Search Works

Retained search is a fundamentally different engagement. You’re hiring a firm, not just posting a job, to act as a strategic partner throughout the entire process.

Here’s what a retained search typically looks like:

Phase 1: Deep Discovery. The search firm embeds with your team. They learn your business, your culture, your leadership dynamics, and the specific outcomes the new hire needs to deliver. This phase alone often takes 2 to 3 weeks.
Phase 2: Strategic Sourcing. Rather than posting a job and waiting, the firm conducts confidential, targeted outreach to 50 to 100+ prospective leaders. Many of whom are currently succeeding in similar roles and not actively job searching.
Phase 3: Assessment and Calibration. Candidates are evaluated against a multi-dimensional framework, not just a resume checklist. Behavioral profiles, values alignment, leadership style, and strategic fit are all part of the picture.
Phase 4: Finalist Presentation. You receive detailed profiles on a small number of thoroughly vetted finalists, each with candid notes on strengths, risks, and tradeoffs.
Phase 5: Offer and Onboarding Support. The firm helps navigate the offer process, coach through negotiations, and co-create a 90-day onboarding plan to set the new leader up for success.

The Hidden Cost of a Bad Executive Hire

When a senior leader fails, the damage extends far beyond their salary. Industry research consistently estimates the total cost of a bad executive hire at 3 to 5x their annual compensation when you factor in:

Lost productivity and team disruption during the failed tenure
Damage to culture, morale, and trust
The cost of re-recruiting and re-onboarding
Revenue lost to stalled initiatives and strategic drift
The founder’s time and emotional energy spent managing the fallout

For a $250,000 executive hire, a failed placement can cost $750K to $1.25M in total organizational impact. Suddenly, the upfront investment in a retained search looks like the most affordable option on the table.

When Contingency Makes Sense vs. When You Need Retained

Contingency recruiting is a reasonable choice when:

The role is mid-level or functional (sales manager, project manager, controller)
The skills are well-defined and the candidate pool is large
Speed matters more than deep cultural alignment

Retained search is the right investment when:

You’re hiring a President, COO, VP, or Integrator
The role is critical to the company’s next chapter
Culture fit and leadership style matter as much as skills
You’ve been burned before and can’t afford to get it wrong again
The best candidates for this role aren’t actively looking

See the Navigating Talent™ Process in Action

At Captains Club, retained executive search is all we do. Our Navigating Talent™ framework was built specifically for owner-operated businesses navigating their most important leadership transitions. Every search is tailored around your culture, your leadership team, and the outcomes that matter most to your business.

The result? A 94% twelve-month stick rate and clients who describe the experience as the most thorough and human hiring process they’ve ever been part of.