Exceptional EA/Chief of Staff ($1,200-$2,250 USD/month + 13th month + education benefit)

I'm Amit, Co-Founder of [Sudowrite]( ---------- ), we make the best AI writing tool for authors. I'm seeking an extraordinary EA or Chief of Staff who can handle complex projects, strategic responsibilities, and contribute proactively to both my professional and personal life.

ABOUT ME AND WHAT I CAN OFFER YOU

Over my career I’ve gotten to start several successful companies, and along the way I’ve enjoyed mentoring and helping employees grow while developing long-term friendships that continue long after our work together.

Examples

- At Sudowrite I work with a colleague who has worked with me as a bookkeeper since 2010 at my previous company. He’s now a trusted advisor and a friend.
- My first virtual assistant and I worked together for five years, then after I sold my company, we continued collaborating on and off for a few years. We finally met in person a few years later!
- My third hire at my previous company had only recently graduated from college. Despite her lack of experience, she impressed me at every turn. I mentored her, and when I sold the company years later, made her the CEO.

In short, I'm in this for the long haul. I enjoy working with exceptional people on ambitious and creative projects, over long periods of time. I value those that can help me, and am deeply loyal to them.

If we work together, I’ll be as committed to your success and growth as you are to mine. This role includes a dedicated annual professional development or courses budget of $1,000 to help you grow in any area you're passionate about. Please share what areas you're interested in learning or improving when you apply!

To learn more about me, you can watch this talk I gave ~10 years ago after I had leukemia ( ---------- ) or read this interview from a few months ago: ---------- .

ABOUT OUR COMPANY

Sudowrite is a profitable AI-powered writing platform serving over 20,000 authors worldwide. We're a team of around 20 people, all of whom play critical roles. We’re small enough that everyone has substantial responsibility, a real say in what we do, and opportunities for growth.

We’re driven by the fact that we’re changing our users’ lives. Authors tell us Sudowrite helped them get back to the work they loved, helped them write more books and make a living from their art, and support their families with their writing. We love that we’re helping people tell their story. Our company has been prominently covered in many media outlets, including The New York Times, The New Yorker, The Atlantic, Wired, The Verge, and many more.

HERE'S WHAT I'M LOOKING FOR

I’m looking for a long-term, trusted partner—someone who will be integral to my success and the growth of Sudowrite. I deeply value stability and building mutual trust, and I see this Chief of Staff as a strategic right-hand position. I’m looking for someone who seeks to do challenging, meaningful work that they can be proud of.

At the same time, I think life should be fun and we should be playful in our pursuits, so it’s also important to me that we enjoy working together. When you apply, tell me in a sentence or two what comes to mind when you think about a playful workplace.

WHY EA/COS?

I’m looking for *either* an EA or a CoS.

If you have have been a Chief of Staff and have years of significant high-level ops experience, I encourage you to apply for the CoS role. If, instead, you have several years of EA experience, please apply as an EA. The compensation will vary based on which role you apply for and your level of experience.

Please note which role you’re applying for in the subject line when you email. Unfortunately, this position is not suited for someone without significant experience in one of these two roles already.

WHO YOU ARE:

- You're highly intelligent, strategic, and resourceful—someone who can "figure anything out".
- Your English is flawless (written and spoken). You communicate clearly and confidently.
- You thrive on managing multiple priorities simultaneously without dropping any balls.
- You have exceptional taste, strong design instincts, and a whimsical, fun digital personality.
- You're tactful and know how to get things done smoothly, yet can apply force when required.
- You have advanced technical skills and are very comfortable with AI tools and software.
- You think strategically and can represent me effectively in critical meetings and decisions.
- You're experienced in project and people management, capable of overseeing complex initiatives from start to finish.
- You have impeccable attention to details. Everyone considers you their most organized friend.
- You have been a Chief of Staff before or have many years of experience as an executive assistant. (See “Why EA/CoS?” above.)
- You are happy to work on Hawaii Standard Time (HST), Monday through Friday
- You’re able to fully commit to this role as your sole employment. Side hustles, freelance gigs, or other part-time commitments aren't compatible with the dedication and focus required. This is a role for someone committed to growing with Sudowrite and doing exceptional, meaningful work.

CORE RESPONSIBILITIES:

- Be a strategic partner by managing operations projects across the company, coordinating contractors, and making sure we hit our goals.
- Firewall my time: schedule, triage and review communication with me daily.
- Personal assistant support: errands, phone calls, appointments, research, etc.
- Research and vet new hires, potential partners, contractors, and tools.
- Look for (and implement) ways to make our company run more smoothly. Draft SOPs and proactively look for ways to make the company, and me, more productive and happy.
- Draft emails, forum, and ---------- posts, crafting authentic, thoughtful responses.
- Represent me in meetings, making decisions aligned with our company’s vision and my goals.
- Administrative support: handle accounts, onboarding, phone calls, travel logistics, and company onsite planning.

HIGHLY PREFERRED (BUT NOT REQUIRED):

- Experience working with US-based technology startups.
- Background in marketing, copywriting, or novel-writing.
- Experience automating common tasks using AI or no-code tools.

**Why This Role is Challenging (and Why You'll Love It)**

This role isn't for beginners—it's designed specifically for an exceptional, experienced EA or Chief of Staff who's ready to take ownership, think ahead, be proactive, and take action. You'll have the opportunity to solve interesting problems and enjoy a very high level of access. However, you must hold high standards for yourself, be self-driven, and deeply trustworthy.

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HOW TO APPLY

Apply *only* if your experience aligns closely with the responsibilities listed above.

1. Write a concise (no more than 500 words), compelling cover letter:
- Tell me why you're uniquely qualified for this role.
- Tell me why you specifically want to work for me and for Sudowrite.
- Describe a situation where you proactively solved a complex problem for a previous employer.
- Tell me about a business book you love and why you love it.
- Include a link to your online profile on a jobs site, website, LinkedIon, etc.
- Include the word "Sudowrite" as the very first word of your cover letter.
- Put this letter in the email body.
- Attach a resume.
- Don’t use AI, write it in your own words, please.
2. Record a video (1-5 minutes) that shows your personality. **Don’t read off a script**, just be yourself. Use Loom and send a link in your email body.
3. Email everything to ----------

WHAT HAPPENS NEXT?

- If you’re chosen to move to the next round, I’ll contact you for more information.
- I may ask you to do a Zoom or asynchronous interview.
- I’ll ask you to complete a (paid) sample assignment.

I look forward to finding the right partner for this critical role!