Senior Relocation and Estate Services Team Lead

Do you like giving back to the community in meaningful ways? Do you enjoy leading people to accomplish important goals? Do you like thrifting, antiquing, or hunting for hidden treasures?

If so, we want to meet you!

Caring Transitions Evanston & Skokie is seeking a responsible, compassionate, and detail-oriented Team Lead who has a heart for service and enjoys being innovative and creative.

In this hands-on leadership role, you’ll lead small teams helping seniors and their families through downsizing, relocating, estate cleanouts, and settling estates with compassion and respect.

You’ll help organize and clean out homes, prepare clients for moves, and research, photograph, and describe interesting items—including antiques, fine art, collectibles, jewelry, furniture, and vintage décor—for sale on CTBIDS.com, our online auction platform.

Every project is different. One day you may uncover a hidden treasure, and the next you may help a senior unpack and settle comfortably into their new home. This is meaningful work where you can see the difference you’ve made for a family at the end of the day.

What You’ll Do

• Lead the Team – Provide on-site direction, delegate responsibilities, keep projects organized, and ensure work is completed efficiently and with care.
• Sort & Organize Homes – Sort belongings into items to sell, donate, dispose of, or relocate to the client's new home.
• Capture the Details – Photograph items to showcase their condition, details, and appeal to buyers on CTBIDS.com.
• Research Treasures – Research antiques, collectibles, artwork, furniture, jewelry, vintage pieces, and other household items.
• Prepare Online Auctions – Assist with lotting, photographing, measuring, researching, and writing accurate auction descriptions.
• Support Estate Sales – Serve as sales staff, cashier, or Team Lead during in-person estate sales as needed.
• Support Seniors & Families – Work directly with clients while treating their homes, belongings, and memories with dignity and respect.
• Assist with Packing & Resettling – Help clients pack for moves, unpack at their new residence, organize living spaces, and create a comfortable new home.
• Complete Cleanouts – Help ensure homes are cleared, organized, and ready for the client's next step.

What We’re Looking For

We’re looking for someone who is dependable, organized, compassionate, creative, and comfortable taking the lead. You should be able to communicate clearly, solve problems, keep a small team focused, and maintain a positive attitude in a fast-moving environment.

An interest in antiques, thrifting, estate sales, collectibles, art, resale, or vintage items is a big plus. Previous leadership, moving, estate sale, retail, organizing, or customer-service experience is preferred.

Candidates should also be comfortable lifting and moving household items, being on their feet throughout a shift, and working in homes, garages, basements, storage units, and senior communities.

Compensation & Benefits

• $21.00 per hour
• Part-time / project-based position
• Eligible for 401(k) benefits after one year of employment
• Opportunity for additional hours based on project volume and availability

Company: Caring Transitions Evanston & Skokie
Position: Team Lead – Senior Relocation & Estate Services
Pay: $21/hour
Employment: Part-Time / Project-Based
Service Area: Evanston, Skokie, Glenview, Morton Grove and surrounding areas
Schedule: Varies based on client projects; weekday and occasional weekend availability may be required.
Benefits: Eligible for 401(k) benefits after one year of employment.