Executive Assistant / Chief of Staff

Read the overview on our job board page before you apply: https://jobs.ashbyhq.com/theacademysf

I’m looking for a right hand operator who loves checklists, operations, and wrangling people.

Over my last two companies, I’ve had an Executive Assistant at each. I rely heavily on them for both personal and professional life management. In turn, I’m an active coach, thought partner, and career champion. The last EA I had (Audrey Bannon - you can look her up) is now Head of People at my company, Maven. She will definitely interview you (though I haven’t even asked her; we just have that kind of trust) and you can definitely interview her.

What you’ll find is that I took great care to teach her everything I could about business, interacting with people, operations. She had access to my inbox, my take on every person I interfaced with, and as a result she got to see exactly how a company operates at every level.

In exchange, she gave me 4 years as EA. Even though she was definitely qualified for more after about 2 years (she learned fast!). And of course along the way, her scope grew every day and her compensation grew accordingly. By the end she was doing the day-to-day operations for almost every non-core function: she ran our offsites, managed my email, built our internal company culture, handled our taxes, managed vendor contracts, etc.

What makes these relationships special is the following:

• I am doing a million things at once. You keep things organized.
• I am hard-charging and provide frequent feedback. You are calm under pressure.
• I never remember anything. You remember everything.
• I am deeply involved in everything at the company. You love learning new things and are excited to help in every aspect.
• I have high standards on experience design and hospitality. You are naturally excellent with people and have good taste.
• HAA is an AI-native school. You have Claude projects for everything in your life.
• I am constantly interfacing with hundreds of people, including celebrities and 16-year-olds. You know how to write and communicate differently with each.
• HAA is in person. You will need to be in person in San Francisco every day the school is in session.

I truly believe this is an amazing opportunity for the right person. It is very likely the right person has never been an EA before, or has ambitions to learn the ropes and grow into a Chief of Staff. As long as you’re willing to do the work, for at least 2 years, then I’m open-minded. Here’s the work:

• Managing my email. AI-assisted for organization but human-written for any critical communication.
• Managing my calendar, travel, etc. Use Calendly for most people, but for the right people it’ll be completely manual. The hardest part here will be picking hotels, restaurants, etc.
• Creating a CRM for the company. Just look at the Academy’s website - we have a massive
• Running the office. You’ll make sure the office is stocked, set up workstations, onboard employees, etc.
• Legal, HR, Finance, Accounting. You can know none of this when you arrive but you must be excited to learn. Over time you will learn these skills and be able to review vendor contracts (especially with AI’s assistance), onboard/recruit employees, manage billpay, etc.
• Managing my personal life. You’ll mostly prioritize my work life, but there will be some personal stuff such as managing my finances or interfacing with vendors at my house.
• Implementing the company’s culture. By working super closely with me, you’ll learn to become a steward of my views on how the company should operate and you’ll do your best to help create that culture within the company.

If this appeals to you, please apply. Prior work experience is not super relevant to me but I’ve had success with former teachers or former operations managers in hospitality industry.