GMass, Inc.: A non-existent assistant (100K+ USD/year)

Headquarters: GMass, Inc.

Hi! My name's Ajay, and I'm the founder of a SaaS company in the email space called GMass.
I'm looking for someone that probably doesn't exist, but I hope you can prove me wrong.  My company, GMass, makes software that turns a Gmail account into an email marketing platform. For the last 10 years, I've been grinding away on all the things that a techy CEO of a promising startup does: coding, marketing, sales, support, administration, responding to email…oh boy, so much email. Which you might expect because we're an email company. 

I need some help with all the busy-work so I can get back to building our product and growing the company.

"Assistant" isn't even the right word for this role, but it happened to make for a good rhyme. "Chief of staff", or "Right hand to the CEO" or "Executive Assistant" are all more fitting, but I’m more concerned with talent and skills than titles. Once hired, you can choose your title.
The person I seek will take control of tasks and projects related to GMass and my personal life, and these items span multiple disciplines from operations to customer support to negotiation to finance on the GMass side to logistical planning and domestic staff management on the personal side.

Skills I'd like you to have:
  1. Email marketing: You should understand the fundamentals of email marketing, either having worked for an Email Service Provider, or having coordinated email marketing campaigns for an organization.
  2. Writing: You must have an expert grasp on the English language. You should be able to write nearly perfect prose without the use of Grammarly or ChatGPT. I consider myself a good writer, and you should  be able to write as well or better than me so you can communicate on my behalf.
  3. Technical: You should be well-versed in Windows and Mac environments and if I hand you a CSV file of data and ask you to clean, sort, and filter the data in a Google Sheet, you should laugh, because it's as second nature to you as breathing. If you know HTML and can write SQL queries, then even better.
If we could travel back in time two months and you were working with me then, here are some projects I’d assign to you:
  1. We have a series of email campaigns we need to send to our user-base of 1-million+ users. Wait until our content producer is finished with the content, then prep, schedule, and monitor all of the campaigns. Then, reply to everyone that replies to the campaign.
  2. We need to run the entire GMass codebase through a static code analyzer in order to pass a security assessment from Google. Given a list of companies that make code analyzers, find the top five that we can use on a free trial basis to get an initial feel for how much work needs to be done on our code in order to be Google-compliant.
  3. A big customer has reached out directly to me and they're upset because they feel like the support team hasn't adequately addressed the issue. Dig in, find out what's going on, and solve the issue for the customer.
  4. I want to build a Hubspot integration into our platform. Research which competitors have such an integration, try all of them out, and then report back to me as to who's doing it well and who's doing it poorly and why.
  5. I need an icon designed for a new screen in GMass. Find a designer on Upwork and coordinate the process to get the icon created from beginning to end.
  6. It's early December, and some key financial decisions need to be made about the company and taxes before the end of the year. Our books are only done through November though. Extrapolate the data for December, and make some financial projections.
  7. I need to plan an in-person retreat for my small leadership team. We need hotels, flights, dinners, and a space to collaborate. Plan it.
  8. The lease on my car is ending next month. I would usually lease a new car, but interest rates are higher than they've ever been since I started driving cars. Determine if leasing or buying is the better option.
While lots of job ads ask for "a self starter" and "a team player" and someone "that can multitask" and has "attention to detail", I find all those requirements silly, because everyone in the workforce should have those skills. Those are baseline skills needed to succeed at any job, including this one.
It's important to have high emotional intelligence so that you have a good understanding of people and how to make people feel good. Do you know what to say to an angry customer? Can you anticipate what will resolve the situation without the customer explicitly telling you?
Finally, it's important that we get along and enjoy working together. If we don't, we'll start to drift, the role will become stagnant, and we’ll part ways. Feel free to start to get to know me from my X profile and my LinkedIn profile. Note: there was a time when I outsourced my social media posts, so if you read anything that feels off-brand, it's probably because I didn't write it. And if you're a good candidate for this quirky, unorthodox, but fun role, then I'm looking forward to getting to know you too.

Other information:

This is a remote position, but ideally you’re in the United States. This is a high-level position for the most experienced of candidates and with commensurate compensation.

How to apply:

Send me an email to a special address I’ve created: Tell me about yourself and how you’d fit into this role. Please include links to any professional social media profiles or online work you’re comfortable sharing with me.
You can count on your application being read by ME and only me, since I…well…don't have an assistant.

To apply: