Sales Associate Team Lead — Estate Sales

Location: Chicago, IL & Surrounding Areas

Engagement Type: Independent Contractor (1099)
Job Type: Part-Time | Contractor Position
Compensation: Paid by day (based on experience)

About Chicago Estate Advisors

Chicago Estate Advisors is a BBB-accredited, full-service estate liquidation company featured in The Economist for revolutionizing the estate sale industry. We help families navigate life’s most sensitive transitions — from the loss of a loved one to downsizing and relocation — with professionalism, discretion, and results. We are expanding our Estate Sales division and seeking a high-performing Sales Associate Team Lead who can hit the ground running.

Position Overview

The Sales Associate Team Lead is a critical, hands-on role responsible for leading the full setup, organization, pricing, and execution of estate sales across the Chicago metro area. You will be expected to transform a standard three-bedroom home into a fully staged, priced, signed, and sale-ready environment within a single eight-hour day — and drive maximum sales revenue over a two-day sale event. This role demands speed, precision, leadership, and an expert eye for value.

Key Responsibilities

Setup & Staging - Lead the full setup of estate sale locations, including furniture arrangement, item display, and merchandising - Hang and position all directional and pricing signage throughout the property - Stage items to maximize visual appeal and buyer flow within the allotted setup timeframe - Manage setup of a standard three-bedroom home within an 8-hour window (extended timelines apply for hoarding or high-volume situations)

Item Research & Pricing - Research items using a combination of online platforms and AI-assisted identification tools to establish accurate, competitive pricing - Platforms used include: Worth Point, Live Auctioneers, 1stDibs, Pinterest, eBay sold listings, Google, and AI image identification tools (such as ChatGPT) for unknown or hard-to-identify items - Identify and flag high-value items including antiques, collectibles, jewelry, art, and specialty collections - Apply percentage-based pricing strategies and markdowns across sale days

Sales Execution - Lead the sales team on the floor during the two-day sale event - Actively engage buyers, answer questions, and negotiate to maximize revenue - Process transactions accurately, including cash, card, and check payments - Perform mental and written calculations for discounts, percentages, and change with accuracy - Ensure all sales are recorded correctly throughout the event

Light Accounting & Cash Handling - Open and manage the cash at the start and end of each sale day - Track all cash, card, and check transactions throughout the event - Reconcile sales totals at the end of each sale day and submit accurate reports- Apply percentage-based discounts and calculate payouts accurately

Team Leadership - Brief, direct, and supervise sales associates before and during each event - Assign roles and responsibilities to team members for setup and sale days - Maintain team professionalism, energy, and focus throughout the event - Report team performance to the Principal Advisor following each sale

Qualifications

Required - Minimum 2 years of experience in estate sales, auctions, antiques, consignment, or high-value retail - Proven ability to set up and stage a full estate sale location efficiently and independently - Strong cash handling skills — must be comfortable with addition, subtraction, and percentage calculations - Experience leading or supervising a team in a fast-paced, event-based environment - Proficiency researching items using platforms such as Worth Point, Live Auctioneers, 1stDibs, Pinterest, and AI identification tools- Ability to lift and move furniture and items as needed during setup - Professional, discreet, and trustworthy — our clients are in sensitive life transitions - Flexible availability including weekends and occasional short-notice scheduling

Preferred / Additional Compensation - Illinois Auctioneer’s License — candidates holding an active auctioneer’s license will receive additional compensation - Experience appraising or authenticating antiques, fine art, jewelry, or specialty collections - Familiarity with mobile POS systems (Clover Go experience a plus)

Incentives & Growth

Competitive per-event contractor rate (commensurate with experience)
Bonus compensation for verified Illinois Auctioneer’s License holders
1099 Independent Contractor engagement

This role rewards individuals who are proactive, sales-driven, and take initiative on the floor. Chicago Estate Advisors, LLC is an equal opportunity employer. All contractors are required to maintain strict confidentiality and adhere to company security and conduct standards.

Independent Contractor Status
This position is classified as an independent contractor role. The Store Associate is
responsible for their own taxes and is not eligible for employee benefits including health
insurance, paid time off, or retirement benefits. Compensation is provided on a daily rate
basis. This is a contract position with the opportunity for consistent weekly hours based on performance and reliability.

Why Join Chicago Estate Advisors?
• Work in a creative and ever-changing retail environment
• Be part of a growing company in a premier Chicago location
• Gain hands-on experience in retail operations, merchandising, and consignment
• Opportunity to grow within the company

To Apply:
Please submit your resume and a brief cover letter highlighting your experience and
interest in Chicago Estate Advisors to admin@chicagoestateadvisors.com and deb@chicagoestateadvisors.com