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Executive Assistant Staffing in Chicago, IL

Hire polished, high-performing executive assistants who can support fast-moving leaders across Chicago’s finance, tech, hospitality, and professional services markets. Ikon Search delivers tailored EA staffing for permanent, contract, and temp-to-hire needs, combining boutique attention with rigorous vetting, compensation insight, and qualified shortlists typically presented within 2-3 days.

Executive assistant staffing consultation in Chicago office

Our Executive Assistant Staffing Services

Flexible EA staffing solutions for permanent, contract, temp-to-hire, and specialized administrative support hiring needs.

EA Recruitment

Specialized placement for Executive Assistants, Senior Executive Assistants, Team Assistants, and C-suite support professionals who can manage calendars, communications, travel, projects, and confidential executive priorities.

Administrative Staffing

Recruitment for Administrative Assistants, Receptionists, Office Coordinators, and front-office support roles that keep business operations organized, responsive, and professionally represented from day one.

Personal Assistants

Discreet recruitment for Personal Assistants and family-office support professionals serving founders, executives, principals, and private households with high standards for judgment, flexibility, and confidentiality.

Contract Staffing

Short- and long-term contract EA staffing for leave coverage, project-based support, seasonal demand, interim executive coverage, rapid scaling, and high-pressure corporate services environments.

Temp-to-Hire

A flexible contract-to-permanent model that lets companies evaluate an executive assistant on the job before committing to permanent headcount and long-term team fit.

Permanent Placement

Direct-hire executive assistant recruitment with culture alignment, reference checks, targeted sourcing, and qualified shortlists designed for durable support relationships with senior leaders.

Recruiter screening executive assistant candidates

Our Executive Assistant Hiring Process

Clarify the Executive Support Need

We start by understanding the executive’s working style, communication preferences, pace, calendar complexity, confidentiality requirements, and company culture, including the expectations common in Chicago’s finance, professional services, and growth-company environments.

Map the Right Candidate Profile

Source and Vet Qualified Talent

Present a Focused Shortlist

Support Offer and Onboarding

Trusted By Leaders

Client Success

Ikon Search supports established firms and growing companies with fast, carefully vetted staffing solutions.

"We engaged with Ikon Search to help us find an HR Manager for our boutique investment bank, and the experience was exceptional. As a specialized financial institution, we needed someone who not only understood the nuances of our industry but also had the right cultural fit for our team. Ikon..."

Boutique Investment Bank

"Ikon Search filled a highly critical PR Director position at a hedge fund HQ in NY. We were to demonstrate our expertise in the financial services sector and a deep understanding of the unique skill set required for the role. We ensured that each candidate was not only highly qualified..."

Hedge Fund
The Ikon Difference

Why Choose Ikon Search?

A boutique staffing partner built for precise, responsive executive assistant recruitment.

Market Speed

Qualified EA shortlists are typically presented within 2-3 days for urgent Chicago hiring needs.

Tailored Focus

We invest upfront to understand culture, executive style, workload, and long-term support goals.

Deep Expertise

Founders bring 25+ years of executive search experience across demanding professional markets.

Flexible Hiring

Permanent, contract, and temp-to-hire models fit Chicago teams scaling or covering critical gaps.

Meet the Ikon Team

Experienced recruiters focused on precise, relationship-led staffing.

Portrait of Kristin Lutz, Head of Contract Services at Ikon Search

Kristin Lutz

Head of Contract Services

Kristin Lutz serves as Head of Contract Services at Ikon Search, the boutique staffing firm she helped establish in 2021. With deep expertise in contract and contingent workforce solutions, Kristin brings a client-first approach to every engagement, investing time upfront to thoroughly understand each organization's culture, values, and long-term hiring goals. Her extensive background in executive search and staffing enables her to connect businesses across financial services, technology, insurance, and marketing with exceptional professionals efficiently and accurately. Kristin is committed to delivering clean, quality-driven candidate pipelines and building lasting partnerships that support sustainable growth for clients ranging from growing startups to established corporations and PE-backed portfolio companies.

Portrait of Connor Brown, Head of Insurance at Ikon Search

Connor Brown

Head of Insurance

Connor Brown is the Head of Insurance at Ikon Search, leading the firm's specialized Insurance, Risk & Compliance recruiting division. With a focused expertise in the insurance sector, Connor works closely with carriers, brokerages, MGAs, reinsurers, and TPAs to identify and place top-tier talent across a wide range of roles. He leverages deep industry knowledge, broad professional networks, and Ikon Search's cutting-edge recruitment technology to present highly qualified candidates typically within two to three days. Connor takes pride in building genuine relationships with both clients and candidates, ensuring every placement aligns with the organization's operational needs, culture, and long-term strategic objectives.

Portrait of Adam Levy, team member at Ikon Search

Adam Levy

Managing Partner

Adam Levy is a key team member at Ikon Search, the boutique staffing firm founded in 2021 with a mission to deliver tailored talent solutions across select industries. Adam contributes to the firm's commitment to pairing rigorous candidate vetting with a deep understanding of client needs, helping businesses across financial services, technology, insurance, and marketing find exceptional professionals. He embraces Ikon Search's core values of tailored focus, market speed, and data quality, working diligently to build and maintain strong relationships with both clients and candidates. Adam's collaborative approach supports the firm's ability to handle diverse hiring engagements, from full-time permanent placements to contract and temp-to-hire arrangements.

Frequently Asked Questions

What is the average salary of an executive assistant in Chicago?

Executive assistant compensation in Chicago varies by industry, executive level, scope of responsibility, and whether the role supports one leader or a full leadership team. Senior EAs supporting C-suite executives, finance leaders, founders, or family offices typically command higher compensation. Ikon Search can support benchmarking by reviewing base salary, bonus potential, hybrid expectations, and comparable market demand.

What is the best staffing agency in Chicago?

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Do you place contract and temporary executive assistants?

What types of executive assistant roles do you recruit for?

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Need Help Hiring an EA?

Talk to Ikon Search about your next executive assistant hire.

Trusted Expertise

Awards and Recognition

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25+ Years Experience

Founder-led executive search expertise and market insight.

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5-Star Rating

Rated five stars on Google Business Profile.

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Boutique Staffing Firm

Tailored talent solutions across specialized hiring markets.

Find Your Next Executive Assistant

Share your hiring goals, timeline, and preferred engagement model. Ikon Search will review your needs and recommend a focused executive assistant staffing approach.

Contact Us Today

For immediate assistance, feel free to give us a direct call at 347 332 9668. You can also send us a quick email at KristinL@ikonsearch.com.