AI-Savvy Chief of Staff to CEO, Multiple Businesses (Sherman Oaks, CA)

****NOTE********* PLEASE read this entire job description before applying. There are specific instructions inside it, and applications that don’t follow them won’t be considered. This role is all about attention to detail, so this is your first test.

You’ll also need to complete a short 10-minute project (details under “How to apply”). It shows us right away that you have both the willingness and the ability to make this a great fit.

A bit about us

I’m an entrepreneur running several businesses at once: real estate development and construction, a telehealth company, a medical spa clinic, a digital marketing agency, and a few other ventures. Things move fast, there are a lot of moving parts, and I need one person who can keep it all organized and make things happen.

I’m looking for a Chief of Staff who becomes my right hand. Not someone who waits to be told what to do, but someone who sees what needs to get done, gets it done, and keeps everyone on track.

We use AI and technology across everything we do, so this person needs to be on the cutting edge. You should be the one bringing new tools and smarter ways of working to the table, not the one catching up.

The role

Full time, in person, based out of our clinic office in Sherman Oaks. Monday through Friday during business hours, with some evenings and weekends when things come up. You’ll also be out around LA for meetings, job sites, and errands, so a reliable car is required.

What you’ll be doing

• Running my calendar, inbox, and priorities day to day
• Following up with teams, vendors, lawyers, contractors, and partners across all the businesses so nothing falls through the cracks
• Tracking projects and deadlines and keeping me updated on where things stand
• Using AI tools every day to work faster: drafting, research, summaries, organizing info, and automating repetitive tasks
• Finding and setting up new tools and automations that save time across the businesses
• Handling basic IT: setting up accounts, devices, apps, and integrations, and troubleshooting when something breaks
• Writing emails, summaries, and documents professionally and clearly
• Helping on projects across the businesses, from marketing to clinic operations to construction
• Personal and local errands when needed

What the right person looks like

First and foremost, a great attitude and a real desire to learn. You’ll be jumping between very different businesses every day, and that should excite you, not stress you out.

You’re very organized, sharp, and a strong communicator. You take ownership and follow through without being chased. To show us you read the full description, start your cover letter with the words “Ready to run it all” before anything else.

You’re an expert with AI and VERY tech savvy. You use tools like ChatGPT, Claude, and other AI apps daily and know how to get real results out of them. You stay up to date on what’s new in tech and AI, and you get excited about finding better ways to get things done. You’re comfortable with Google Workspace, Excel, Slack, project management apps, and automation tools like Zapier or n8n.

You must be reliable, mature, and trustworthy. You’ll be handling sensitive business and personal information, so discretion is a must. You show up on time, ready to work, and you care about doing things right.

Requirements

• 3+ years as an executive assistant, chief of staff, operations manager, or similar
• Expert level with AI tools and very strong with computers and technology
• Basic IT skills (account setup, devices, software, troubleshooting)
• Excellent writing skills in English
• Strong with Excel / Google Sheets
• Understanding of basic digital marketing is a big plus
• Reliable car and valid driver’s license
• Must live in or near Los Angeles

Preferred

• AI classes or certifications (please list them in your application)
• Experience with automation tools (Zapier, n8n, Make, or similar)
• Bachelor’s degree

How to apply

Submit your resume through Indeed with a cover letter that includes:

• Your answers to this short project:
• You walk in Monday morning and have three things waiting: a contractor needs an answer on a change order by noon, a patient complaint came in at the clinic, and I’m asking for a summary of a vendor proposal before a 2pm call. Walk us through how you’d handle the morning in 4 to 6 sentences.
• Find 3 private meeting rooms or coworking spaces within 15 minutes of Sherman Oaks that can be booked by the hour. List the name, hourly rate, and link for each.
• Tell us about one AI tool or automation you’ve used to save real time. What was the task and how did you set it up?
• Any AI classes or certifications you’ve completed
• Why you’d be a great fit for this role
• Your required pay
• Links to your social media so we can start getting to know you

Applications missing any of these won’t be considered. If you’ve sent everything, we’ll get back to you quickly.

Job Type: Full-time Schedule: Day shift, on call, weekends as needed Supplemental Pay: Bonus opportunities Experience: Executive assistant, chief of staff, or operations: 3 years (Required) Education: Bachelor’s (Preferred) Certifications: AI certification (Preferred) Location: In person, Sherman Oaks, CA 91403

Pay: $62,100.00 - $74,900.00 per year

Work Location: In person