A Pretty Cool Executive Assistant Job

Okay let's skip through the fluff and cut to the chase. I have a small law firm that is completely virtual. The good news? You get to work from home, the coffee shop, your childhood bedroom, wherever really.

I am biased here, but I think what we are building is pretty cool and this will be different than other law firms you have worked at.

While awesome, there is good things and bad things about the position.

Let’s get the bad news out of the way first:

The hours are weird. I’m a small law firm. My work is unpredictable. This is a part-time position but I may not always have enough work for part-time. So, if you’re looking for something full-time to start, then this is no longer the “coolest” contract Executive Assistant job, it just became the “suckiest” and probably isn’t a good fit. I’m looking for someone who can join the team with these part-time hours, but feel like this is their full-time home.
Things are scattered at the moment, I won't sugar-coat it. We have some systems, but others are not there yet, which is where you come in, we need an order deliverer, drill master, someone who brings order to the chaos that is our firm.
My availability is sporadic at best. If you are looking to learn on the job and have everything spelled out for you, then this likely isn't a good fit. Sometimes the instructions will be vague or ill-defined. We are parents with young families, between traveling, sales calls, producing legal work, networking and caring for family there just isn't always time to spend hours on end training.
We do have rush projects on occasion, we are a law firm and there isn't little I can do about that other than accept we are at the whim of our clients.
This is an executive assistant position. There is a lot of administrative work - email clients, calling potential clients, organizing documents, sending emails. If you don’t get jazzed about administrative work and are not the type of person that likes to talk to people, this probably isn’t a great fit for you.
Review points 1-4.

Now let’s talk about the good stuff:

1. My office is virtual...which means you can wear yoga pants, pajamas, or a costume. Really the idea is that you can wear whatever you want. Just think of the amazing money you’ll be saving on ‘work clothes’ and the time in the morning that you won’t have to spend on a work routine, heck you don’t even have to brush your teeth if you don’t want to (although I do highly recommend it….good dental hygiene and all). You’re probably already used to this as someone who’s been around the block in the online world, but it’s still worth mentioning a plus!

2. The work is cool (Sometimes). You will be working with me and my associate attorney. You will have the opportunity to get involved and leave your mark on our firm within the boundaries of the vision and culture we are trying to build. I am not here to micromanage and sometimes I am almost too hands-off, but that is the beauty of it all, this role is for the entrepreneur at heart. Now let me be clear, not ALL the work is glamorous, there is a lot of administrative work, engagement letters, managing my client pipeline, scheduling meetings and the like. So if you do not get amped about being the administrative guru, this likely isn't a great fit for you.

3. I’m not big on stress. I will expect you to work efficiently and get things done. I’m not big on double-checking your work or having a bunch of back and forths just to get a task done - plus I am not an expert in most of the tasks you will be doing, which is why I need you to take charge and get ‘er done the best way you know! That said I firmly believe that AI TOOLS ARE JUST THAT...TOOLS NOT A REPLACEMENT FOR CRITICAL THINKING. So while I love the use of ChatGPT, Claude, Grok, Perplexity or any other tool you may have out there, I don't have any tolerance for it being a replacement for your critical thinking. This is a hard-line.

4. The hours can be flexible-ish. I will work with your schedule to get a routine that works for you, at the same time this is still a part-time position and I am looking for someone who can be mostly available during the hours that I am available to help attend calls, take notes, triage emails, etc. so that I can focus on the the parts of the firm that are my strengths. My preference is that you’re within 1+/- hours CST

5. You will be the star of the show. As a small law firm, I need someone that can do “all the things.” Eventually as your hours build there will be an opportunity to niche down into certain work, so if you are looking for a consistent daily routine this probably isn’t the job for you. If you want to have variety, setting up invoicing, reminding me to follow-up with particular clients and holding me to it, and calling up clients to schedule meetings the next, you may be the right person for the job!

6. You’ll have a ton of autonomy + the opportunity to bring your ideas to the table and boss me around when you need me to get things done. Seriously, I am so strapped for time that the more I can outsource the better. In other words, I want you to take charge!

7. You don’t have to run your own business! Maybe you’ve been around that block, and it wasn’t for you. Now you can have all the benefits of supporting people to create their dream businesses that provide freedom, without all the headaches + expenses of actually building your own empire. It’s like the best of both worlds! You don’t want the pressures of marketing + growing your own business (way too hard), but you do enjoy being the right-hand person to someone else who is doing it.

Now, let’s talk about the job requirements:

1. You need to be the type of person who gets joy out of getting things done. Every day, you will bang out a list of stuff. Fun stuff. Important stuff. Necessary stuff.

2. You like being on the computer a lot, and have a solid understanding of online software, an ability to learn new tools and maximize what we have at hand - and you totally geek out on all of it. If you would rather be outside gardening this probably isn’t the job for you. We use a lot of different software, so you will have to be prepared to get up to speed on what we use. Sometimes, we decide that the tool we are using isn’t what we need so we change.

3. You will be emailing + talking with clients, potential clients + the team. So, you need to enjoy talking with people and giving/getting direction, and be able to do it with love + empathy...even if you’re having a terrible, not-so-good, very bad day.

4. You are a free thinker + willing to take an outcome and make it happen. As much as I would love to help you through every problem, I am stretched thin most days and there are weeks that I am just simply unavailable. So you need to be the kind of person that can problem solve, take information, a set of permissions, and achieve the outcome. In the same vein, I believe that AI (ChatGPT, Grok, Claude, etc.) is a wonderful tool, but it isn't a replacement for your brain and your ability to make decisions. So there will be no just copying and pasting from ChatGPT and no AI work slop.

5. You love to organize things that may feel currently chaotic (aka my tech stack) and make them work way better than I ever could have. And you work well when given an outcome, a good playlist, and uninterrupted space.

6. You love thinking critically. You’re thinking three steps ahead. You can take the information given you to, ask follow-up questions, and aren’t afraid to probe even deeper when something seems ary or unclear.

7. You are interested in making an impact through a part-time position that can grow into a full-time position. We are growing and have the ability to scale quickly if I can build the capacity to go out an market. Part of your job will be helping me free up the space so that I can focus on growing and scaling. If I am able to spend more time marketing because all the other pieces of the puzzle are working together, there is more profit in the business and more that can be shared with everyone involved in making it happen.

In short, your job is to help us in any way you can drive our mission forward + continue to free us up from questions, decisions, and the things I don’t need to be involved in. And to have fun at work (who wants a job that isn’t fun?!?).

But what I don’t expect is perfection. Tools are teachable, but I do expect you to have a solid understanding of the online business world and I want you to get excited about diving into the strategy for someone else’s business. I expect intelligence, energy, organization, resourcefulness and a get it done attitude.

To learn more about the company, check out our

Some specific things you’ll get to do:

Use my project management software (ClickUp) to keep projects + initiatives moving forward and on time.
Making plans and executing on them efficiently. You’ll be responsible for making sure I’m on track too, so you must be comfortable taking charge + delegating up!
Tracking metrics (how are we doing on hour utilization? Are we over budget with a flat fee client? Are our newsletter subscribers down?)
Responding to clients, potential clients and making sure their feedback is heard!
Holding initial screeners with potential clients.
Tracking my sales pipeline.
Helping with all of the administrative stuff: emails, preparing invoices, collecting fees from clients, collecting documents and information, onboarding clients, off-boarding (is that even a word?) clients, and making sure the client experience is stellar!
Create ideas + plans for how to leverage what I have already created, more strategically throughout the year.
Jump in where needed!

If this is a job that gets you so excited that you would even do it for free, I would totally accept that offer from you. But if you prefer compensation (I totally get it…I prefer getting paid as well) this is what I can offer: -This is an part-time position with a starting salary of $15,000. This is a virtual role, so you can work from wherever is most comfortable -- but I’d prefer someone who is within 1 hour +/- of the Central Time zone.

Unfortunately, given my size, there are not many benefits that I can provide at this time. But with the right person in place that is open and willing to be a part of our growing team, all the goodies will be on the table: profit-sharing, incentives, bonuses, a work computer, 4-5 weeks of PTO, health insurance, etc. While this is all a part of my dream, I am just not there yet.

I’m looking to bring my Executive Assistant on board as soon as possible, but I will spend the necessary time to find the best fit both in abilities and culturally.

I can’t wait to meet you!

Applications must be submitted by November, 21 2025 at 11:59pm CST . Late applications will not be accepted.

Job Type: Part-time

Pay: From $15,000.00 per year

Expected hours: 20 per week

Application Question(s):

What is your familiarity with using technology?
Share with me about a time that you had to think critically when given a task with little to no guidelines or explanation

Experience:

Executive administrative support: 5 years (Required)

Work Location: Remote

The Law Office of Joshua A. Lowenthal, PLC

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A Pretty Cool Executive Assistant Job