High-Ownership Personal Assistant for Retirement Logistics & Travel Planning

I am looking for a high-ownership assistant to manage personal logistics for my amazing mother. You will offload important administrative tasks of ours and eventually transition to being her dedicated assistant. She is approaching retirement and I want her to retire from worrying about anything in her life ever again - whether the bills are paid, if the car is insured, keeping track of emails, booking flights, managing a schedule.

I am a 30 year old software engineer and entrepreneur who finds unique ways of getting things done quickly. I will share with you how I think about problems and some of the tools I use - I like productivity tools and try to use them where I can. My mom is a single parent Spanish-speaking immigrant about to graduate law school. Right now my sole focus is getting her retired - a goal that has many steps that I need help with. That’s why we need a highly capable assistant like you!

This is a pivotal moment for her and one of deep importance to me. Your work will have a direct and meaningful impact every single day. Once she’s retired we want to start traveling together so your work will turn into more fun stuff like researching ideas for where to travel to, what to do, planning our days, etc.

What You'll Do (Sample Responsibilities):

* Create a system for you and my mom to track important dates, appointments, and household maintenance. Using a tool like Trello to follow up on tasks.
* Act as her go-to person for any and every task, from making calls on her behalf to patiently providing tech support.
* Research/call local establishments for information, quotes, appointments
* Call service providers (banks, insurance, internet, cell phone, etc.) For things like change of service or billing disputes
* Consolidate all of my mom’s online accounts - reducing her down to one or two emails, clearing out her email, closing unused accounts, cleaning up her passwords
* Find a local personal assistant to help with in-person tasks
* Trial software tools to make our work more streamlined
* Plan a complete 3-day weekend trip, including booking travel and creating a summarized itinerary suitable for my mom and I, presented in a saved Google Maps list
* Anticipate and order any items that my mom needs e.g. Glucose monitor refills or a Netflix subscription. Hunt for items for sale on Facebook Marketplace, eBay, etc.
* Sell her items online as we downsize the house. Posting and managing items of ours for sale on Facebook Marketplace, Craiglist, OfferUp, Depop, eBay, etc. This includes research to come up with an accurate title, description and competitive price, and coordinating with potential buyers to schedule a pickup that works for our schedule

Skills & Qualifications

Must-Haves:

* Fluent in both English and Spanish (my mom speaks Spanish).
* Ability to make and receive calls during U.S. Business hours (est/pst).
* An active Facebook account for managing Marketplace listings.
* Experience managing phone/email communications and acting as an intermediary e.g. Calling the bank, waiting on hold, and patching us in when they’re ready.

Must be proficient with these tools:

* Slack and all its features for organized communication.
* Trello, Todoist, or similar shared task manager
* ChatGPT for research, and ability to verify information externally
* Google Calendar (managing multiple shared calendars), Google Maps (creating/sharing lists), Google Sheets and Google Forms.

Extra tools we will use, bonus points if experienced with them:

* Loom for communicating things visually (much more efficient than text).
* Krisp for transcribing our meetings and generating action items.
* Advanced prompt engineering knowledge or having a system for using LLMs would be a huge plus. Experience with Perplexity AI for research, or other LLMs like Gemini/Claude.
* Calendly and Doodle to streamline scheduling.
* Canva for creating basic flyers; Pixlr, Photoshop, or Lightroom for photo editing; Midjourney for image generation.
* Tango for creating step-by-step browser guides.