Executive Assistant - AI Consulting Business Operations (20-40hrs/week)

Hi

My name is Howie! Thanks so much for reading this job posting. A little about me before jumping into the role: I'm a fun, friendly 30 year old software engineer living in California. I train Jiu Jitsu most days, travel a lot, do camping/road trips, am creative in both my work and personal life, and do amateur photo/videography that I'm going to start making content with. I live an active life and it's about to get more busy as I've just launched my consulting business and it's already moving fast. The rest of this job posting is dense and overwhelming so wanted to show that I was a real person first, not some business executive.

My ----------
My LinkedIn: ----------
Business page: ----------

UPDATE March 5: Thanks to everyone for their applications so far! I got flooded with work so will be following up this weekend. Will try my best to respond to everyone then, thanks

ABOUT THE ROLE
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I run a consulting business based in San Francisco and Miami where I provide guidance on companies' operations, build any software they may need, and connect them to any new AI tools that would make them more efficient. Clients include tech startups, accounting firms, a law firm and individuals so far, so you'll get exposure to those industries. It's been one month but already I need help as I'm being quickly referred by my existing clients. My 3 month goal is to grow this from just me to an agency with other engineers, a designer, video editor, content/marketing. I need a sharp, resourceful assistant like you to be an extension of me in my personal life and for the business.

- The 20hrs/week for me will be a mix of my personal tasks and tasks for the business. If we end up needing more hours that's no problem for me, just estimating 20hrs for now.
- You'll also have the option to work 10hrs/week for my sister and her fiance's accounting firm that they run (or if you know anyone feel free to refer them)
- Then there will be frequent opportunities for you to do work directly for our clients as needed. For instance, if the law firm has a project they need help with. This can pay $7/hr.


WHY WORK WITH ME
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You won't be doing repetitive work. This is a dynamic, high-trust position. Here's what makes this worth your time:

You'll work with the latest AI tools - I use and build AI tools for a living. I live in Silicon Valley so I'm the first to hear about any new tools, and I get to meet a lot of the people building them. You'll be using those same tools daily. I hope we can work together forever but if not you'll come out of this role with hands-on experience that you can put on your resume or use to start your own business!

You'll learn my productivity systems - I work fast and efficiently. Together we'll create systems to get things done faster than 99% of the world. I invest in making us better - if you need something to do work more efficiently it's yours. If you want to develop a skill that will help the business go for it. The skills we build together will be beneficial for any future position.

You'll gain experience across multiple industries.

There's a real growth path - The right person's responsibility and pay will grow with the company.


SCHEDULE & COMPENSATION
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Hours: 20-40 hrs/week as stated above
Availability: Mostly on your own time but some work (like calling businesses) will need to be done during Pacific Time business hours: 9AM - 5PM PST. And I'm sometimes busy with clients during those hours so if you and I need to meet then it might be done outside of those hours e.g. 8AM or 6pm PST. So flexibility is a plus.
Rate: $5-7/hr USD (based on experience). Any ad hoc work for other clients billed at $7/hr.
Growth: Compensation reviews at 3 months and 6 months


WHAT YOU'LL BE DOING
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Business Tasks

- Researching and trialing new tools and services and reporting back on whether they're worth it
- Finding and vetting video editors for both business and personal content. Sourcing a designer for brand and visual identity work. Finding a front-end software engineer for project-based work. Identifying someone to help with brand strategy and content creation. A part-time junior software engineer
- Drafting and editing client emails and cold outreach in a real person's voice
- Industry research: What AI tools are being adopted in accounting? What does a mid-size law firm's tech stack look like?
- Setting up and optimizing the business profiles across platforms: Creating and optimizing profiles on Google Business Profile, LinkedIn Services, Clutch, G2, Yelp Business, and other relevant directories for consultants
- Conducting a digital presence audit - searching for the business across Google, LinkedIn, and other platforms, documenting where we rank, who appears above us, and identifying specific opportunities to improve visibility
- Seeing what other agencies do, copying them, maybe reaching out to work together or become friends
- Project manager - coordinating with me, clients and contractors
- Administration e.g. managing expenses in Quickbooks

Personal Tasks

- Managing schedules
- Making calls to US businesses on my behalf - banks, government agencies, insurance companies, service providers
- Emailing companies for customer support
- Email management: cleaning up inboxes, following up on deliveries
- Sourcing things I need to buy from Facebook Marketplace, Amazon, eBay
- Researching and booking travel arrangements: hotels, campgrounds, events, interesting stops, scenic routes, activities, events, restaurants
- Reaching out to professional services for things like moving, printing services, etc


TOOLS
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You do NOT need experience with most of these. Having experience is a plus. What matters most is that you can pick up new tools quickly e.g. via YouTube tutorial. That's the skill I care about. Though some of these are very useful for any work you may do so even if you don't apply I highly recommend looking into them!

- Slack - communication, task assignment
- Loom - video recording. Besides Slack we'll be communicating through video more than anything
- Claude / ChatGPT (will ask to see your chat history because there are smart ways to communicate with these. This is the best way I can see how you think)
- Zapier / Make / n8n - workflow automation (HUGE plus if you have experience here!)
- Bitwarden - password and credential management (like LastPass or 1Password)
- OpenPhone or Google Voice - US business phone number
- Linear - task management (like Jira)
- Trello - personal task management
- Wispr Flow - voice-to-text dictation
- Granola - AI meeting notes
- Google Workspace
- Canva - light design work
- Superhuman - high-speed email management
- Notion - documentation and SOPs
- Perplexity - AI-powered research
- Claude Cowork - desktop automation agent (big plus if you have experience here)
- Tango - step-by-step guides and SOP creation
- Toggl Track - time tracking and reporting
- CRM Tools e.g. Attio


QUALIFICATIONS
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First thing's first - if your application sounds like it was generated by AI, I'll ignore it. That doesn't mean don't use AI to help write it - I'm using it to help me write this posting. But I'm editing it heavily so that it has my voice. A real voice. Your work will involve the same - clients don't want to get emails that sound like AI. So your application is the first test of this.

Must-haves:

- Strong written and spoken English. Reliable internet. Quiet environment to make calls.
- Available for a 2-3 hour window during US Pacific business hours (PST)
- Day to day flexibility would be really great. You can mostly do tasks whenever best for you but I might ask for things at any point during my day - like making a cool graphic for a last minute client presentation - and it would be nice if you were available.
- Available (some) Saturdays. Since I'm busy with clients during the week, my personal tasks end up on the weekends. Can work this out - maybe Sunday and one weekday off, and if we agree to work on off days we can do so at a higher rate.
- High agency - you take initiative and ownership, solve problems before being asked
- Attention to detail - you have high standards and double-check that all instructions were followed before completing a task
- Comfort with technology and a demonstrated ability to learn new tools independently
- Experience making phone calls to US businesses on behalf of a client

Strong pluses:

- Experience with any of the Business or Personal work listed above
- Strong background in computers e.g. IT
- Any content creation background (graphics, photoshop, video editing, social media)
- Background in marketing, SEO, branding, or helping grow a business's online presence
- Strong written and spoken Spanish
- Familiarity with business administration or bookkeeping
- Experience with any of the Business or Personal tasks listed above - please note them in your application!
- Trustworthy Facebook, LinkedIn profiles

Dream bonus (not expected):

- Experience with Zapier, n8n, Make, or similar automation tools
- Junior-level software engineering skills
- Experience as a travel agent or travel planning professionally


HOW TO APPLY
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Please engage with the business page I just created - follow, like, comment
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Send a resume with references

Part 1: Video Introduction
Record a video introducing yourself, your experience in general, and your experience with any of the work or tools listed above. I'm big on "show vs tell" so if you have samples of your work or can show off some of your workflow that would be amazing. Even if you script this try to sound natural!

Part 2: Sample Task
Quickly find some software or AI consultant or consulting firm based in Miami and write up an analysis on them - could be their website, their services, their clients, their marketing. Then write them an email (don't send it) saying what interests you about them and how our businesses could potentially collaborate. Using AI is completely ok just remember in the end it has to sound human. Bonus points if this is all shown in the video, but can also just paste the write-up and email in your application.


WHAT HAPPENS NEXT ---------- . Top 5-10 applicants will be invited to do a paid task ($5 USD) to evaluate your speed, how you figure things out, and your communication style.
- 2. Top ~5 candidates will be invited to a video interview. To make sure we're a good fit! Will notify everyone of results on this day.

I am always looking to help - if you make it to the final rounds where we meet but don't end up working together, I will keep your name in mind any time I hear of someone needing VA support.

I'm so so so so excited to work with you!!! Thank you