Startup CEO Seeks Executive Assistant.

I am the CEO of a startup, and we’re working on some really exciting stuff. It is by no means a sure bet just yet, but we have some great momentum and just added an awesome investor to the mix. One of the problems I’m struggling with right now, especially as a first time CEO three years in the making, is making sure I am using my time in the best possible way, and that’s why I’d like to hire you.

I’ve had an executive assistant before, but they keep getting promoted into other important roles in our company like sales, product management and human resources. Maybe this will happen for you too, or maybe you love being an EA and we’ll work together for a decade. I’m cool with either one.

I used to think an executive assistant was too bourgeois or posh for a startup CEO, but as I’ve progressed in the lifecycle of our company and discovered a very different reality: you help make sure the trains run on time. You 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 fundraising due diligence, planning a company retreat, 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 husband and I need to make sure to plan dates and vacations with him). I would like to compensate you in the top quartile of the salary range for this position, because I know you will work a lot of hours and carry a lot of my worries as your worries. I work hard to be a good person, but I know you will interact with me in some of my most stressful moments and this might stress you out, too. A good person for this role would be more calm than me.

I need you to be in the office when I’m in the office, relieving me of administrative work so that I can focus on 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 an executive. It’s going to be a rollercoaster ride.

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:

• Managing my agenda as a gatekeeper against any waste of time
• Booking professional and personal travel
• Making sure all expenses are properly recorded
• 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…)
• 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 office where I am hosting including startup poker, monthly community happy hours, 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, it’s a bit of a shield. I’m working on toning it down but it is somewhat engrained in my personality.

I like to give direct feedback, I will tell you what could be better and I will also tell you what is good. I won’t yell or swear, but I will be brutally honest. If this makes you uncomfortable you’re not going to be happy, 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 we’ll probably get along.

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 dissmive 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 danielle@mattermark.com with your cover letter (e.g. a personal letter from you on why this role would be a meaningful next step in your career and your professional happiness) as well as your resume.

I can’t wait to meet you!