Senior Transition Specialist (Organizing, Downsizing, Packing) - Chicago

Top Tier Transitions LLC; Chicago (IL); On-site; USD 25,000 - 28,000; Part time

Benefits offered by this job

Flexible scheduling

Competitive pay

Chicagoland travel

Job summary

Top Tier Transitions LLC is seeking a compassionate, detail-oriented Senior Downsizing & Move Specialist for part-time, flexible hours in the Chicago area. You will assist seniors with relocation, downsizing, estate preparation, and coordinating donations, with a focus on empathy and discretion.

Ideal candidates bring patience, organizational skills, and strong communication. Travel within the Chicagoland area and lift up to 25 lbs are part of the role.

Qualifications

• Compassion and patience in client interactions.
• Organizational skills to handle fast-paced environments.
• Clear, professional communication with clients and team.
• Attention to detail when handling personal belongings.
• Physical stamina to stand, move, and lift items.

Responsibilities

• Provide hands-on support to seniors and families during relocation, downsizing, estate sales, and home prep.
• Deliver compassionate, high-touch service to clients navigating transitions.
• Bundle and sort belongings into Keep/Resale/Donation/Disposal categories.
• Coordinate donations to local organizations for respectful rehoming.
• Assist with packing/unpacking to create functional living spaces.

Skills

Compassion & Patience

Strong Organizational Skills

Professional Communication

Attention to Detail

Physical Stamina

Job description

Downsizing & Senior Move Specialist

Part-Time | Flexible Schedule | Chicago

About Top Tier Transitions

At Top Tier Transitions, we specialize in senior relocation, downsizing, and estate management services. From sorting cherished belongings to creating a comfortable new home, our team delivers thoughtful, trustworthy, and high-value solutions with care and discretion.

Whether managing an estate sale, decluttering a lifetime of possessions, or preparing a home for sale, we handle every detail with respect—because transitions aren’t just about moving. They’re about honoring memories, preserving dignity, and supporting families during meaningful life changes.

Make a Meaningful Impact

At Top Tier Transitions, we believe life experience is an asset.

We are seeking compassionate, dependable individuals to join our team as Senior Downsizing & Move Specialists. This role is ideal for professionals who bring patience, emotional intelligence, and strong organizational skills—and who find purpose in helping others during important life transitions.

Many of our most successful team members come from backgrounds in education, healthcare, caregiving, administration, customer service, or have developed strong organizational skills through managing households and families. If you are calm under pressure, detail-oriented, and naturally supportive, you will thrive in this role.

This is meaningful, flexible part-time work for individuals who value people, professionalism, and purposeful service.

What You’ll Do

As a Senior Relocation & Downsizing Specialist, you will provide hands‑on support to seniors and their families during relocation, downsizing, estate sales, and home preparation projects.

No two days are the same, but your responsibilities will include:

Client Support & Transition Assistance

• Deliver compassionate, high‑touch service to clients navigating emotional transitions
• Assist with downsizing, decluttering, and organizing belongings with care and sensitivity
• Pack and unpack household items to create functional, comfortable new living spaces
• Thoughtfully sort and stage belongings into Keep, Resale, Donation, or Disposal categories
• Support estate sale preparation and item organization
• Help prepare select items for approved resale channels when appropriate
• Coordinate donations to meaningful local organizations so items are respectfully rehomed and continue serving others within the community

Logistics & Physical Responsibilities

• Lift and move items (up to 25 lbs; larger items handled by professional movers)
• Clean and prepare homes for sale or new occupants
• Travel locally to client homes throughout the Chicagoland area

What We’re Looking For

We value empathy, integrity, and efficiency. The ideal candidate demonstrates:

Core Skills & Qualifications

Compassion & Patience – You treat every client with dignity and understanding
Strong Organizational Skills – You thrive in fast‑paced, ever‑changing environments
Professional Communication – You interact confidently with clients, families, and team members
Attention to Detail – You handle personal belongings with care and accuracy
Physical Stamina – You can stand for extended periods, navigate stairs, and lift up to 25 lbs

Additional Requirements

• Reliable transportation and willingness to travel within the Chicagoland area
• Smartphone proficiency (scheduling, time tracking, documentation)
• Background check required prior to hiring

Our Core Values

Act with Empathy – Every client’s story is unique. We listen deeply and tailor our approach with sensitivity and respect.
Live with Integrity – Clients entrust us with their most personal spaces and possessions. We operate with discretion, reliability, and transparency.
Simplify the Process – We manage every element of the transition so families can focus on what matters most.
Rehome with Pride – We thoughtfully rehome, resell, or donate belongings with care—ensuring each item is treated respectfully and, when possible, continues to bring value within the community.
Strive for Excellence – Our white‑glove standard means going above and beyond—offering refined, reliable, and responsive support from start to finish.

Why Join Top Tier Transitions?

Make a Real Impact – Support seniors and families during some of life’s biggest transitions
Flexible Scheduling – Ideal for parents, retirees, students, or those seeking supplemental income
Collaborative Culture – Work with a caring, supportive, and professional team
Competitive Pay – $18–$20 per hour, based on experience
Growth Opportunities – Join a growing company with potential for advancement

Join Our Mission

If you’re ready to bring compassion, organization, and excellence to a role that truly matters, we would love to hear from you.

Chicagoland Area