Become the founder’s right hand at a fast-growing AI writing startup ✍️🤖
Overview
No salary declared 😔
Remote / Hawaii
Expires at anytime
We’re nice people making AI tools for novelists.
We do this because we love storytelling and we’re optimists. We believe AI is a phenomenal collaborator, not a destroyer of worlds.
As writers living in the most interesting time for writers in history, we have an opportunity to reinvent how people write.
We feel honored that we get to do this work.
30,000+ paying writers love and use us.
20,000,000,000+ words written. That’s a lot of novels.
3,000,000+ projects in every genre imaginable.
9 full-time staff and 10 contractors. Small is beautiful.
3+ years of profitability. We’re building to last.
0 VCs on the board telling us what to do.
Chapter 2
The Actual Job Listing
I’m seeking a Right Hand to the CEO (aka business operations whiz).
Before we meet each day, you’ll have gone through my Slack, email, and task list. You walk me through the 5–7 things that truly need my attention—verbally, over coffee, in 10 minutes. For each one, you’ll have loaded the context so I can make a fast call. The other 30 items, you’ll handle, defer, or file. I never see them.
Throughout the day, you’re a buffer between me and the incoming stream. When something needs my judgment, you bring it to me. When it doesn’t, you do it.
Your job is to make sure I spend 80% of my time on the things only I can do. However you need to accomplish that—whether it’s planning a company retreat, negotiating with vendors, running errands, or anticipating what I or the company need—that’s the job.
Some days will look like this…
Prepping context for a $1MM/yr vendor negotiation
Running SQL analysis to support a tax decision
Writing a detailed SOP and using AI to automate it
Reviewing job applications for a new role
Other days will look like this…
Getting a contractor agreement signed
Researching babysitters & other travel logistics
Approving expense reimbursements
Ordering supplies because we ran out
The most important job: automating your own job.
We’re an AI company, and we’re leveling up how we do our jobs daily. Anything you and I find ourselves doing over and over, it’ll be your job to automate.
If that range gives you an identity crisis, this isn’t your role. If it sounds like a fun puzzle, keep reading.
What Success Looks Like
Month 1 - You’re sitting in my meetings, learning how I work, and taking things off my plate.
Month 3 - You’ve automated many of our recurring projects, you’re preparing decisions, and I have 3x more time to do the work only I can do.
Month 6 - You independently own projects—maybe retreat planning, maybe vendor negotiation, or something new. The ceiling is as high as you want to take it.
About You
You’re the most organized person your friends know
You can context-switch between a spreadsheet and a grocery order without feeling like one is beneath you
You use AI tools all the time. And you’re excited to teach yourself how to use them even better
You have previous operations, chief of staff, executive support, or jack-of-all-trades-at-a-startup experience
You have impeccable attention to detail. You’ve noticed errors in this listing and you will point them out
You’re comfortable with ambiguity, can change course fast, and juggle multiple projects at once
You can read a 20-message email thread and summarize it in two sentences
You can say “You’re wrong about this and here’s why”
You’re kind, thoughtful, have great taste, and you’re fun to be around
Nice to have
You can work in-person in Honolulu, HI
Comp: $80-130K, depending on experience. Plus profit share and generous equity in a profitable, growing company.
Our Culture & Perks
Company Retreats
We’ve been to Hawaii (twice), Portland, Palm Springs, Mexico, and more!
Kind Coworkers
You spend a third of your life at work. It should be with people you like.
Unlimited Books
Love to read? So do we. The books are on us!
Remote-only
For full-time roles, live anywhere within U.S. timezones.
Low-drama Culture
We work with a coach to support communication and openness.
Profit Share
We offer competitive compensation and a profit share.
Insurance Coverage
We offer full health and dental coverage so you don’t die.
401(k)
Because no matter how great this job is, someday you’ll want to retire.
Generous Equity
Not selling lottery tickets here, but if we win big, we’re in it together.
Chapter 3
Why you shouldn’t work at Sudowrite
We have a company cult.
It’s called “CLG” and stands for Conscious Leadership Group. It’s all about becoming more conscious in life and work by paying attention to your feelings (b/c they’re there either way, and they’re gonna cause trouble if you ignore them), keeping your commitments, acting with integrity, and so on. Very reasonable, non-culty stuff, packaged in a slightly culty way.
We work with a coach we love and she helps us learn and practice this stuff. We won’t make you do it, but you’ll probably want to.
CLG has helped many of us communicate more clearly, grow closer, and ultimately know ourselves and each other better.
We’re kinda normal, kinda not
In a lot of ways I think Sudowrite is a pretty normal startup. We make software. People pay for it using subscriptions (I know, ew). We are smart and motivated to make good things. We invent new things and take pride in our work. All pretty normal.
And in some ways it’s not a normal startup. James and I have started companies before and sold them, and we weren’t looking to start a company. Unlike most startups today, we didn’t do this to take part in an AI gold rush. In fact, we started a couple years before ChatGPT existed.
James and I were happily writing fiction and made Sudowrite for ourselves. Then it kinda blew up. Since we’d been through this before, we decided to do things a bit differently.
We raised some money, but not from random VCs. Instead, we carefully brought in founders, writers, directors, and operators. We decided from the start that we wouldn’t chase ever larger and riskier funding rounds, giving up control along the way. It turns out this matters a lot.
This is our fourth year of profitability, and the fourth year we plan to do a profit share. We’ve been featured in The New Yorker and everywhere we care about. We have infinite runway. Our growth has come predominantly from word of mouth. So far, so good.
We want to grow, but not just so we can raise more money and say we’re killing it. We want to grow because it gives us the resources to do cooler and more ambitious things. For example, last year we launched Muse, the first AI model made just for fiction. We’re working on more AI models for writers, and prototyping completely new ways to write.
We have over 30,000 paying authors. At our current revenue, a typical go-for-broke money-losing VC-backed startup might have 40 employees. We’re at a fraction of that.
That means we run things tight and stay focused on the important stuff. It also means everyone has actual impact. Not pretend impact, like share an idea at all-hands and maybe we’ll prioritize it if a VP claims it as their own idea next quarter.
Anyone can come up with an idea on Monday, spec it out the same day, and put it into action a couple days later.
Chapter 4
How to Apply
Write us a note. Tell us why you want to do this and why we should hire you. Let us see your personality.
Show us what you can do. Link or attach things. Tell us about the projects you’ve nailed, the people you’ve helped.
Send it to us. Email [email removed - click apply for more details]
What happens next…
1.
We’ll follow up to ask questions.
2.
We’ll reach out to set up a call.
3.
We’ll offer you a short paid project or go through an exercise together on a call.