Executive Assistant - Right Hand to Founder

Hello future sidekick :)

I run a high-ticket online coaching and education business built on faith and family values, and I'm looking for an Executive Assistant who can become my right hand — the person I hand almost anything to and trust it gets done, or gets solved.

This is not an entry-level VA role. I need someone with real experience who thinks for themselves, and who's comfortable working inside a faith-driven business and its culture.

You’ll also be in charge of handling anything I need which is sometimes all over the map - from client care to light design.

Here’s the areas you’ll own:

1. Client Care & Concierge

Helping clients in our premium programs with login/platform issues, onboarding, and general "make sure they have everything they need" support

Managing the requests for cancellation, billing issues, etc.

You’ll also be hosting/running support zoom calls - usually Bi-weekly at 10am PST. You just host the call and guide clients through the process.

2. Executive Support

Inbox and calendar management for me directly, including scheduling with clients

General project management — keeping initiatives moving and on time, flagging what's falling behind

3. Tech & Platform Management

- Website updates (Wordpress)
- Platform migrations
- Publishing blog posts and podcast episodes on schedule
- Troubleshooting when something breaks — finding the problem, not just reporting it
- Light video editing

4. Marketing & CRM Ops

- Tag/segmentation management
- Email automation management in Kit
- Email sends to active clients inside our CRM
- Canva graphics and slide decks when needed
- Building new products and funnels in ThriveCart


5. Organization

- Keeping Google Workspace/Dropbox files clean and organized as you go — not just when asked

Our tools:
- Slack, Google Workspace, Canva, ThriveCart, ClickUp, Kit (CRM), Zoom, Mighty Networks, Wordpress, Podbean.

Requirements: You must have:

- Minimum 5 years of experience as an executive/virtual assistant, ideally supporting a coaching, course, or online business

- Fluent, nuanced English — non-negotiable. You need to understand idioms, tone, and the way clients actually talk, not just formal business English. This is a client-facing, judgment-heavy role.

- A track record of being reliable and showing up. I do not work with flaky people.

- Genuine comfort with tech: you don't need to be a coder, but you can find a problem on a platform or in a workflow and troubleshoot it yourself before escalating

- Availability to overlap with US Pacific Time mornings daily + available for occasional meetings and calls on Pacific time.


You are NOT a fit if:

- You have not been an executive assistant for at least five years.

- You do not have experience with high ticket clients or an online coaching business before

- You wait to be told exactly what to do, every time (after you’ve been trained)

- When something breaks, your instinct is to report the problem and wait — instead of coming with 2-3 options you already tried or considered

- Tasks and projects fall off your radar without a heads-up — when new things get added to the plate, I need you to raise the "let's reprioritize" conversation, not let something quietly drop off

- You're flaky — late or a no-show without communicating ahead of time

- You lean on ChatGPT (or similar tools) to do your thinking or write for you instead of using your own judgment

- You're looking for a low-commitment, part-time, or short-term gig (my last VA was with me for 5 years)

- You're not comfortable with ambiguity or fast-changing priorities - things change quickly in an online business


What I actually care about most:

I need a critical thinker and a self-starter who treats this business like it's partly theirs. I give my exec assistant the authority to make things better and make decisions. If you spot a sales page that could convert better, a website fix, or a gap in the client experience, I expect suggestions and feedback and - if it’s not a structural change to my business - just make the change :)

The people who impress me most communicate proactively, have a real eye for detail, and go above and beyond what was asked without being told. Over time, the right person starts to think like me — less "assistant," more "sidekick."

To apply:

Start your application with the words "Blue Pineapple" in the first sentence, so I know you read the full posting.

- Include your resume - which should include your last 3 jobs & how long you worked there. Ideally with references.

Then answer these three things:

1. Why are you the perfect candidate for this role?

2. Describe a time you found a problem on your own and solved it before anyone asked you to. What did you do?

3. What hours (in your local time) can you consistently work, and what's your overlap with US Pacific Time?

Applications that skip "Blue Pineapple" or copy/paste a generic cover letter will not be considered.

* do not use AI to write your letter - I am very experienced at telling when it’s AI that has written it, and it will immediately disqualify your application.

Note: salary is negotiable based on experience and skill level

I look forward to reading your application!