Startup Seeks Executive Assistant.

I have been leading this startup since we launched in May of 2017, and we’re working on some really exciting stuff. It is by no means a sure bet just yet, but once again we have some great momentum and hope to establish a plan to expand by the end of 2021. One of the problems I’m struggling with right now is making sure I am using my time in the best possible way for myself and the sustainability of the company, and that’s why I’d like to hire you.

As I’ve progressed in the lifecycle of our company, I have learned that I need someone to help make sure the trains run on time. You will also help me offload administrative work that is not consistent in volume — and when it spikes I don’t sleep, and that’s not good for anyone (great examples include executing marketing plans, following up with clients, planning a company training or strategic planning sessions, etc.)

How the Role Works

I need someone to partner with, who can be fully trusted with managing my calendar, my email, my phone, my contacts, as well as coordinating aspects of both my professional and my personal life (one of my cofounders is my wife and I need to make sure to plan dates and vacations with her, for example). I work hard to be a good person and communicate with compassion, but I know you will interact with me in some of my most stressful moments and this might stress you out, too. When I am stressed, it's not uncommon for my true caring to seemingly evaporate. The ideal person for this role would be calmer than me.

I prefer you to be “in the studio” when I’m in the studio, relieving me of administrative work so that I can focus on the responsibilities that come with leading the company. Together, we will navigate a time of incredible growth for the business as well as a great deal of personal growth for me as I train up the next wave of executives to lead our growth. It’s going to be a rollercoaster ride and we will throw our hands up, sometimes in ecstasy and sometimes in surrender.

Some of the Things You’ll Do

I am doing many new things now that I wasn’t doing a year ago, so I imagine your role might evolve as well. Here are some things I know I would like to entrust you with managing right away:

  • Making sure I eat lunch (I know, but it is actually one of the biggest reasons I’ve identified why I have an unproductive day…)
  • Managing my agenda as a gatekeeper against any waste of time
  • Coordinating lunches and dinners with my senior team, key customers and partners, and other constituents
  • Collecting and driving a list of key decisions I need to make each day, such as: things I need to sign, documents to review, important emails, invitations, deadlines, reminders, etc
  • Coordinating events in the studio where I am hosting including training new technicians, monthly community tournaments, recruiting meet and greets
  • Taking on random tasks that are important to me but difficult to complete in between a day fully booked with meetings

What I’m Like to Work With

I am pretty brusque, at least day-to-day. Sometimes this might come off as uncaring, but once we’ve worked together for a few weeks I’m sure you’ll see that I care, possibly too much. Let’s be honest, in these extreme moments, I can throw tantrums as a way of shielding what is really going on. I’m working on toning it down but there are patterns woven together over decades, so I will often need patience and slowing things down to get underneath it all. Plus, there are volumes on the line already, and more and more getting written every week. I expect the pressure to increase over time, not decrease.

I like to give direct feedback, I will tell you what could be better and I will also tell you what is good. I will be persistently honest. If this makes you uncomfortable you’re not going to be happy together, so you shouldn’t work for me (I mean, I don’t want to make you unhappy!). If this feels like something you’d prefer, then let’s meet and get into the thick of it.

I am not interested in doing anything not directly connected to the goals of the company. You will discover very quickly what I think is important and what I think can be ignored. I will be pretty open with you about things I think are worth our attention, and things that aren’t. For example, I get invited to tons of events and tons of speaking opportunities and you’ll probably find I am pretty dismissive of about 95% of this stuff. It’s not because I have a big ego, it’s just that if I did all of that there would be no time for the research, product design, leadership, and other stuff I do internally. It’s weird, it seems like this stuff would be valuable, but doing in-person events doesn’t always scale… so we have to be picky.

The Long Term

I’m cool if you’re not my EA forever, but I want someone who will do this job happily and with great focus for at least 1 year. Beyond that, if you discover an aspect of the company you are thrilled about I’d love to promote you into one of our teams and task you with hiring and training your replacement.

Together, we will build a company and if you want to learn what it’s like to run a company then I invite you to come run a company with me.

Please email with a personal letter from you on why this role would be meaningful to you, your career, and your professional happiness as well as your resume.

I can’t wait to meet you!

futurist | game designer | technologist | consultant