Chief of Staff placement
The Chief of Staff Who Gives You Your Week Back.
The Windermere Agency places chiefs of staff and senior executive assistants with Orlando founders for a flat $4,500 fee, a $750 deposit applied and a 90-day replacement guarantee. Candidates are personally interviewed and fully screened before introduction.
$4,500 flat fee | $750 deposit applied | 90-Day Replacement Guarantee
The role
What a Great Chief of Staff Does.
When a founder needs someone to run the company's week, not just their own, the role is a chief of staff. We place people who can hold priorities, run a meeting cadence and carry decisions through without being the founder.
- Owning the operating rhythm: priorities, meetings, follow-through
- Running special projects and cross-team initiatives
- Preparing board, investor and leadership materials
- Acting as the founder's proxy with partners and the team
- Building the systems a growing company lacks
How It Works
How a Chief of Staff Search Runs.
- 01
Inquiry & Introduction
A one-minute inquiry tells us who you are and what you need. You receive a confirmation right away, and we respond within 24 hours.
- 02
Discovery & Client Intake
A conversation by phone or email, then a short division-specific intake so we understand the role, the schedule, the compensation and what matters most.
Company and hiring contact, position and reporting structure, work location, employment type, compensation and timeline.
- 03
Proposal & Engagement
A clear proposal: scope, what is included, the flat fee, deposit and payment terms, and how we will communicate. The search begins when the agreement is signed and the deposit is received.
- 04
Search & Candidate Selection
We source, interview, verify references and complete the screening the role calls for, then present a curated shortlist with updates on the schedule we agreed.
Business candidates are screened for the role: professional references, a background check and verification of the skills the position requires.
- 05
Interviews & Placement
We schedule interviews, gather feedback, arrange trials or assessments where appropriate, and help with the offer through acceptance and a confirmed start date.
A culture assessment built around your team sits alongside the interviews.
- 06
Onboarding & Ongoing Support
We confirm the start went well, check in after the first week and again around 30 days, and stand behind the placement with the replacement guarantee.
Corporate placements carry our 90-day replacement guarantee.
Questions about chiefs of staff
Ready to Hire the Right Person?
We're not here to fill a position. We're here to find the right person.
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