Chief of Staff

I'm Amit, CEO of Sudowrite (www.sudowrite.com/), a company that makes an AI writing tool for authors. I'm seeking an extraordinary 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 since 2010 at my previous company.
- 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, she became 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! The role’s monetary compensation is between $2,000 and $2,500/month, dependent on experience. We also pay 13th month.

To learn more about me, you can watch this talk I gave ~10 years ago after I had leukemia (www.youtube.com/watch?v=9AP1hoNJkMk) or read this interview from a few months ago: founderthings.substack.com/p/interview-amit-gupta.

**About our company, Sudowrite**

Sudowrite is a profitable AI-powered writing platform serving over 20,000 authors worldwide. We're a team of around 25 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. At the same time, I think life should be fun and we should be playful in our pursuits, so it’s 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.

I’m looking for someone who seeks to do challenging, meaningful work that they can be proud of. You should want to be part of a high-trust culture where your contributions will be recognized and crucial to our collective success.

**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, efficiently, 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. Your friends consider you their most organized friend.
- You have been a CoS before or have several years of experience as an executive assistant.
- You can 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 departments, coordinating contractors, and making sure we hit our goals.
- Firewall my time: schedule, triage and draft email, review communication with me daily.
- Personal assistant support: errands, phone calls, appointments, research, family support.
- 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 discord 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.
- You won’t be doing all these things all the time! But this is a taste of the kinds of things I’ll ask of you.

**Highly Preferred (but not required):**

- Experience working with US-based startups.
- Background in marketing, copywriting, or novel-writing.
- Strong creative instincts, especially in content creation and idea generation.
- 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 Chief of Staff who's ready to take ownership, think ahead, be proactive, and significantly improve my professional and personal life. 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.