Executive Assistant / Operations Assistant (Remote)

Executive Assistant / Operations Assistant (Remote)

We are looking for a highly organized and resourceful Executive Assistant / Operations Assistant to help manage podcast operations, sales follow-up, content production, scheduling, and day-to-day administrative tasks.

This is not a narrow “calendar-only” assistant role. You’ll be involved in multiple parts of the business, including podcast production, client follow-up, social media posting, CRM organization, SEO content research organization, and administrative support.

You do not need to be an expert in all of these areas already. What matters most is your ability to learn quickly, follow instructions carefully, think critically, stay organized, and adapt to different tasks without constant supervision.

This role is ideal for someone who learns by watching videos and knows how to use AI to ask questions first before asking me. I've provided all the resources with transcripts that have all the information you need. I strongly encourage using AI tools, transcripts, tutorials. Please always double-check the transcript and resources provided with AI before escalating questions to me.

Put grapejuice in the subject line and use 5 AP to apply (no more no less). For your ideal rate, also put $8/hr. This is the starting salary with a $1 per year raise depending on performance. If you put more or less for desired salary you won't be considered.

Responsibilities
Podcast & Content Support
Edit long-form podcast episodes using Descript
Use AI tools inside Descript to help clean up episodes
Cut long-form episodes into short-form clips for social media
Convert clips into vertical format for platforms like Instagram Reels, TikTok, LinkedIn, and YouTube Shorts
Upload and publish content to social media platforms
Organize podcast assets and content files
Podcast Guest Outreach & Scheduling
Send LinkedIn connection requests and outreach messages to attorneys and professionals
Coordinate podcast scheduling with guests
Access calendar availability and propose meeting times
Send scheduling emails professionally and accurately
Keep communication organized and professional at all times
Sales & Lead Follow-Up
Review notes and transcripts from sales calls and cold calling sessions
Write personalized follow-up emails based on the context of each lead
Understand different lead situations, such as:
Interested now
Needs more information
Follow up later
Not interested currently
Update lead statuses in Google Sheets and sales pipelines
Maintain organized records of communication and follow-up timing
Web & SEO Assistance
Generate free website mockups/design concepts using AI tools like Claude
Follow SEO content workflows and automations
Prepare AI-assisted articles for final review
Understand basic website and SEO terminology
Assist with website-related administrative tasks
Administrative & General Support
Handle multiple small operational tasks throughout the day
Follow written SOPs and instructions
Communicate clearly and consistently
Stay organized while managing multiple ongoing responsibilities
Required Skills
Strong written English
High attention to detail
Comfortable learning software quickly
Organized and reliable
Able to work independently
Comfortable with AI tools and modern software
Basic understanding of websites and digital marketing concepts
Ability to adapt communication based on context
Tools You May Use

We will provide access to paid tools and subscriptions as needed.

Examples include:

Descript
Canva
Claude
Google Sheets
Google Calendar
LinkedIn
AI-assisted SEO tools and workflows
Application Process (Assessment Required)

We do not want generic cover letters.

Instead, applicants must complete the assessments below so we can evaluate real-world problem solving, organization, communication, and adaptability. You will create a Google Drive Folder and make it public to share your assessments. The only thing you need to respond with is the Google Drive folder. If you write anything else outside "grapejuice" in the subject line, use 5 AP and the Google Drive folder link you will not be considered at all.

Assessment #1 — Canva Business Card

Create a simple professional business card for yourself using the free version of Canva.

Requirements:

Use your own name
Include a headshot of yourself
Include your contact information
Make it look professional and clean
If you don't have a logo for yourself create a simple one

Submit:

PNG or PDF export

Assessment #2 — AI Website Mockup

Using the free version of Claude or another AI tool, generate a homepage design concept for a business. Create a modern homepage mockup inspired by a professional SaaS website like Wix. The text and images you have to update so that it uses information about yourself and your abilities as an executive assistant. You can generate images with Chat GPT or Google Flow and have Claude update them in the design. You are not being evaluated as a designer or programmer. This assessment is focused on your ability to use AI tools to create organized, professional-looking output.

Requirements:

Include a hero section
Include services
Include a call-to-action
Must look professional and modern

Submit:

Full page screenshot along with HTML provided by Claude

Assessment #3 — Sales / Podcast Guests Follow-Up Evaluation

Here's an example cold calling / follow-up transcript that you'll use to draft the emails and update the leads in the sales pipeline:
0:00 Hey, Robert, it's Ted, Ted Martinez. Umm, since last time we spoke back in May of last year, I came up with a podcast interviewing insurance defense attorneys to help the forensic accounting community.

0:14 And I was just curious if you got a chance to check it out. Umm, no? Did you not know about it?

0:22 How did you think I hooked- I came through, uhh, Mr. Reynolds. I'm- I'm sorry? Mr. Reynolds? No? No, I'm trying to figure out how you know me.

0:32 How I know you. Oh, I- I just called you last year, so I help forensic accountants, uhh, with their marketing.

0:40 And so I called you, I just called called you last year. I said, okay. Yeah. Can you send me- can you send me information?

0:47 I don't, uhh- You I don't That's correct.

1:01 Uhm, Gotta tell ya, I'm, I'm quite busy with it.

1:16 Like, uh, I still like to get enough that I can turn things down. You just gotta keep them coming, right?

1:24 Never have to pick a case. I'm coming and turn them away rather than wondering when my next one's coming in.

1:32 It's a much better feeling. Yep. Awesome. I can look it over. Perfect, yeah. I'll send it over and then, uh, if it's okay with you, can I give you a call?

1:41 Maybe, um, Thursday? Get your thoughts, see what you thought, if anything. Uh, Thursday is a horrible day. Uh, if you wait until next Wednesday.

1:48 Okay. Okay. Yeah, around this time. Yeah, uh, if it goes to voicemail, just- means I'm busy with a client, okay.

2:02 Okay. Okay, perfect. Okay. Definitely can do. Thank you so much. We'll try to answer. Thank you. I'll take it. Bye.

2:09 And it's Ted. Ted Martinez. We emailed last year. And since then I came up with a podcast interviewing insurance defense attorneys to help the forensic accounting community and- I was just curious if you got a chance to check out the podcast.

2:28 If not, I can just send you the link. It's a public link. Uh, other than that, Brian, thank you so much for your time and happy Tuesday.

2:36 Bye. It's not in the center of Phoenix, so how can I help you? Hey, Farid, please. Um, I'm sorry he's not available at the ---------- nt, could I- .

2:48 Take a message. Uh, sure. I, uh, I was just calling to see if he'd seen the podcast, like the Forensic Litigation podcast.

2:59 You can just- that would be the message. Okay, who and first? Ted Martinez. Okay. I will let him know.

3:17 Okay, perfect, thank you so much. Yep, you have a good one. You too, bye. you Umm, Sandra.

3:29 Yes. Hi. Hi. This is Ted Martinez. So, we emailed last year, uh, around June. June. So you again. And since then, I came up with a podcast interviewing insurance defense attorneys to help the forensic accounting community.

3:44 And I was just curious if you'd gotten a chance to check it out. Um, I have not. Okay. Uh, is it something that would interest you?

3:53 Can I send it over? It's just free. Uh, it's just like a public link I can send to you. Thank you.

4:00 That's fine. Okay, umm. Okay. Awesome. So the email I have for you is ---------- ls at ---------- . That's correct. That's still a good one.

4:11 Okay, perfect. And just curious, what are you doing right now to getting in front of attorneys? Um, actually, I, I, my consulting business, I'm doing compliance investigations.

4:30 This is not something that, you know, when you reached out before it was, um, I thought you were looking for, like a forensic accountant for some things, but, um, it didn't seem to work out, so that's fine.

4:44 Oh, gotcha, gotcha. And I have, I have business that I have engaged- So this is not something I'm pursuing at the ---------- nt.

4:53 Oh, okay, okay, got it. I can't, well, thank you so much for your time. Thank you. I have better. Hey, Marcus, it's Ted.

5:07 Ted Martinez. Since we emailed last year in June, I came up with a podcast interview- doing insurance defense attorneys to help the forensic accounting community.

5:17 And I was just curious if you had gotten a chance to check it out. If not, uh, feel free to let me know or text me or call me and I can send you the link.

5:26 Otherwise, Marcus, thank you so much for your time and happy Tuesday. Bye.

Here's how a podcast conversation might look (which you will be the one conversing with them and scheduling them but for the purpose of this exercise just update the podcast guest accordingly in the Google Sheet)

Podcast Guest Example #1

Ted:
Hi Rachel. I have a podcast to help the expert witness community. I bring in litigation and trial attorneys as guests.

You can find more information here:
----------

Would you have 60 minutes sometime this month to come on as a guest?

Rachel:
Hi Ted, thanks for reaching out. I took a quick look and it seems interesting. I mainly work with medical malpractice attorneys so I think I could contribute.

Ted:
Awesome. Would either of these times work?

Tuesday April 7th from 1pm-2pm EST
Thursday April 9th from 11am-12pm EST

Rachel:
Thursday works better for me.

Ted:
Perfect. I'll send over a calendar invite shortly.

---

Podcast Guest Example #2

Ted:
Hi Michael. I host a podcast where I interview litigation attorneys to help expert witnesses better understand how attorneys evaluate and hire experts.

Here's the podcast:
----------

Would you be open to being a guest sometime this month?

Michael:
Possibly. What kinds of topics do you usually discuss?

Ted:
Usually things like:
- what attorneys look for in expert witnesses
- credibility
- report quality
- deposition mistakes
- communication with juries

Michael:
Got it. Yeah, I’d probably be interested. My schedule is pretty packed the next two weeks though.

Ted:
No worries at all. Would one of these work later in the month?

Monday April 20th from 2pm-3pm CST
Wednesday April 22nd from 10am-11am CST

Michael:
Tentatively yes on the 22nd. Can you follow up with me closer to that week?

Ted:
Absolutely.

---

Podcast Guest Example #3

Ted:
Hi Jennifer. I came across your profile and saw your experience with construction litigation. I run a podcast for the expert witness community where I interview attorneys and consultants involved in litigation matters.

Would you have any interest in coming on as a guest?

Jennifer:
Hi Ted. Thanks for reaching out. I’m not really familiar with the podcast. Do you have a link?

Ted:
Absolutely:
----------

Jennifer:
Thanks. I’ll take a look.

Ted:
Sounds good. If it makes sense after reviewing it, I’d be happy to coordinate around your schedule.

Jennifer:
I watched a few clips and it looks professionally done. I’d potentially be interested sometime in May.

Ted:
Perfect. Here are a few possible times:

Tuesday May 5th from 9am-10am PST
Thursday May 7th from 1pm-2pm PST

Jennifer:
May 7th should work assuming nothing changes with trial prep.

Ted:
Understood completely. I’ll pencil that in and follow up closer to the date.

Update leads and podcast guests in a Google Sheet following this format. Make a copy of this document and add it in the Google Drive folder with the rest of the files.
---------- (these are examples here, you will update them with the transcripts written out in this job description)

Your task from the cold calling / follow-up transcript and the podcast guest outreach:

Identify which leads need follow-up
Write appropriate follow-up emails (pro tip: the shorter and more casual the email the better)
Categorize the leads properly
Update a mock sales pipeline spreadsheet

We are evaluating:

Attention to detail
Context understanding
Communication quality
Organizational ability
Sounding like a human

Assessment #4 — Simple Design Task

Create a circular GIF that alternates between:

Your headshot
Your favorite animal

We are evaluating:

Ability to follow instructions
Creativity
Resourcefulness
Comfort with simple digital tasks

Assessment #5 — Problem Solving & Attention to Detail

You want to download Descript for Windows.

What is wrong with this link?

----------

Explain:

what the issue is
how you identified it
what you would do instead

You may use AI tools if needed.

We are evaluating:

logical thinking
attention to detail
ability to troubleshoot independently
comfort using AI to solve small technical problems

Assessment #6 — Website & SEO Fundamentals

Create a Loom video walking through each parts of this on a website. Creating a free WordPress website is simple, if not ask AI to show you how to inspect a page's HTML and you can show me this. Your Loom video has to show your face live. You don't need a 4k camera but people with no camera, super dark backgrounds to where your face can't be seen, extremely loud surrounding noises won't be accepted. If you don't create a video at all you won't be considered.

What is a title tag?
What is a meta description?
What is alternative text (alt text)?
What does “above the fold” mean?
What is content relevance on a website?
How do broken images affect a website?
Use Gemini AI to explain what a canonical tag is.

I'm not expecting expert-level SEO knowledge. We want to see whether you can understand foundational concepts and explain them clearly.

Administrative & General Support

I will prioritize your tasks on a daily basis. You will work on them exactly in the order in which I give them to you.

There will be trainings provided for other tasks. You will get paid to watch these trainings, therefore, timing is of importance. The job starts at 7am MDT sharp and ends at 3pm MDT. There is a lunch break you can take, ideally at 11am MDT so I know you're at your lunch break if you don't respond.

Daily communication is done through Google Chat so make sure your notifications are turned on. "My notifications were turned off." "I don't know why I didn't hear it" are not valid excuses. During working hours I expect fast communication and responsiveness through Google Chat.

I never expect someone to work extra but if you're falling behind or taking too long to do tasks and not taking the initiative to catch-up then this is not the position for you.

Google Drive Folder Naming Convention:
Name your Google Drive Folder "PWD-Firstname-Lastname-Assistant-Application"

Ideal Candidate

This is an AI-first role. We encourage the use of ChatGPT, Claude, Gemini, Canva AI, Descript AI, and similar tools. We are not testing whether you memorize information. We are testing whether you can use modern tools to solve problems efficiently. If you cannot figure out these tasks with the help of AI then this position is not for you.

This role will continue evolving over time, so adaptability is important.