Personal Photo & Digital Organization VA

I am looking for an extremely organized, detail-oriented virtual assistant to help organize a large collection of family photos and videos.

This is a personal/family project, not a social media position. I have years of digital photos from everyday family life, vacations, birthdays, holidays, kids' activities and special events. My goal is to turn them into a well-organized photo library that is easy to find, use, print and eventually turn into photo books.

Responsibilities

You will help:

Sort photos and videos chronologically
Organize photos into a consistent folder system by year, month and/or event
Identify vacations, holidays, birthdays and other major events
Identify duplicate or near-duplicate photos
Identify blurry photos, screenshots and obvious unwanted images
Move questionable images into a REVIEW FOR DELETE folder — never permanently delete photos
Identify the best photos from an event or group
Create folders such as BEST PHOTOS, PRINT, PHOTO BOOK, etc.
Rename folders and files when helpful
Maintain a consistent organizational system
Potentially help create family photo books in the future

Most work will initially be completed through shared cloud folders rather than direct access to my personal accounts.

Who I'm Looking For

You should be someone who genuinely enjoys organizing things.

You must be:

Extremely detail-oriented
Comfortable working with thousands of photos
Able to recognize chronological patterns and group related photos
Consistent with naming and folder structure
Comfortable using Google Drive and cloud-based photo/file systems
Able to follow detailed instructions without needing constant supervision
Careful with private family photos
Comfortable asking questions when something is unclear rather than guessing

Experience organizing digital photos, Google Photos, Apple Photos, Dropbox, Google Drive, Lightroom, photo books or large digital file libraries is a plus.

Hours & Pay

This will begin as a paid project/trial with approximately 500–1,000 photos.

If we work well together, there is a substantial amount of additional photo organization work available and this could become an ongoing part-time position.

Please include your desired hourly rate in your application.

How to Apply

Please answer ALL of the following questions. Applications that do not answer them will not be considered.

Tell me about a time you organized a large number of photos, files or digital documents. What system did you use?
Imagine I give you 800 family photos from 2024. They include a Disney vacation, hockey games, birthdays, screenshots, everyday photos and duplicates. Explain exactly how you would organize them.
You find 12 nearly identical photos of two children standing in front of Cinderella Castle. What would you do with them?
You find a photo that you believe should be deleted, but you aren't sure. What would you do?
How would you name a folder containing photos from a family vacation to Belize in February 2026?
What programs or platforms have you used for photo or digital-file organization?
Have you ever created a photo book? If so, which service did you use?
What is your preferred hourly rate?
How many hours per week are you currently available?
At the very beginning of your application, please write the words PENNY LANE so I know you read the entire job description.

Please do not send a generic application. I care much more about organization, attention to detail and your thought process than a long résumé.