Senior Transition Specialist

Help Seniors. Stay Active. Do Meaningful Work.

Caring Transitions of Milford is looking for dependable, compassionate people who want more than just another job.

We help seniors and their families through some of life’s biggest transitions—downsizing, moving, estate sales, organizing, and home cleanouts. Every project is different, every family has a story, and every day you have the opportunity to make a real impact.

This is ideal for someone who enjoys helping people, likes staying physically active, and takes pride in a job well done.

Why People Love Working With Us

✅ Meaningful Work That Matters
Help seniors and families during important life transitions with compassion and respect.

✅ No Two Days Are The Same
One day you may be packing a home, the next staging an estate sale, setting up an online auction, or helping a client settle into their new community.

✅ Family-Owned Company
We’re a local business that values teamwork, accountability, and treating people the right way.

✅ Flexible, Project-Based Scheduling
Great for retirees, parents, students, first responders, tradespeople, or anyone looking for rewarding part-time work.

✅ Active, Hands-On Environment
Skip the desk job. Stay moving, problem-solving, and making a difference.

What You’ll Do

• Pack, organize, sort, and unpack household belongings
• Assist with moves and resettling services
• Set up and operate estate sales
• Photograph and inventory items for online auctions
• Sort items for donation, sale, recycling, or disposal
• Assist with home cleanouts
• Deliver outstanding customer service to clients and families
• Work alongside a team that genuinely cares

We’re Looking For People Who

• Enjoy helping others
• Are dependable and show up ready to work
• Take ownership and solve problems
• Communicate professionally with clients and teammates
• Work well independently and as part of a team
• Are comfortable using a smartphone and mobile apps
• Have reliable transportation
• Live within 30 miles of Milford

Physical Requirements

• Lift and carry up to 50 pounds
• Bend, kneel, climb stairs, and remain active throughout the day
• Work in homes of varying sizes and conditions
• Occasionally work outdoors as projects require

Our Core Values

Help First
Lead with compassion and empathy.

Find the Solution
Think critically and solve problems.

Extreme Accountability
Own the outcome and follow through.

Professionalism Always
Treat clients, families, and teammates with respect.

Passion & Purpose
Make every project better because you were part of it.

Position Details

Position: Senior Transition Specialist
Location: Milford, CT and surrounding communities
Schedule: Part-Time / Project-Based
Hours: Primarily weekday daytime hours
Pay: Starts at 20/hr 

This isn’t just moving boxes.

It’s helping a daughter prepare her mother’s home for sale.
It’s helping a veteran move into a safer living environment.
It’s helping families reduce stress during difficult transitions.

If you’re looking for work that combines purpose, teamwork, and variety, we’d love to meet you.

Apply today and help us change lives—one transition at a time.