Greywing (W21)
The Operating System for Maritime

Chief of Staff

1+ years
About Greywing

Greywing is a digital platform that tracks ships and optimises everything that gets on or off.

We connect hundreds of public and private data sources - like satellite tracking, crew and fuel reports, GDS, and port restrictions - to provide immediately actionable intelligence on vessel operations.

Our efforts are currently focused on making crew changes cheaper and faster, and in making sure the thousands of men and women who keep our economies functional get home safely to their loved ones.

We work with two of the largest ship operators globally to digitize their operations. They give us the real life experience to automate their businesses and our vision is to deploy the same techniques to the long tail, creating a single operational platform for shipping.

About the role

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 finalised a 2M USD Seed round after coming out of Y-Combinator W21. One of the problems I’m struggling with right now is making sure I am using my time in the best possible way, and that’s why I’d like to hire you.

I used to think a Chief of Staff 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 including making sure I book and take leave to spend time with my girl friend and do not schedule midnight calls over the weekend.

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
  • 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.
  • 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 function best in a routine and like to run my day to a schedule. Ideally we check in AM and PM and then get to work in between.

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.

The Long Term

I’m cool if you’re not the Chief of Staff 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. For the right person you might progress into being the COO, but who knows?

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.


Full time role, ideal candidate will already be in Singapore. Salaries are high, with competitive equity.

The Team

I am a former Royal Marine Commando that has built a business in maritime from nothing to 4 million in turnover.

Our CTO has published multiple papers across technology, from Formal verification in cryptocurrencies, human-computer interaction, embedded glucose monitoring to baseline optimization in chemistry and physics. He has also built software and hardware serving hundreds of thousands of users across southeast Asia, in fintech, insurtech, robotics, for companies like National Geographic, Ethereum, and SGX.

How to apply

If you're interested, please reach out to [email protected] with a short Loom video answering the following questions (or any you'd like):

  1. What should we know about you? Background, capabilities, what you think your strengths are.
  2. What interests you about us?
  3. Tell us a little about the most memorable project you've worked on. What were the hardest parts? What were the best moments?


Greywing currently has a state-of-the-art vessel routing tool, as well as the industry's first structured data collection tools for state actor and vessel data - both public and private.

Our first priority is human-augmentation, by using intelligent path-finding algorithms to navigate this data to provide actionable intelligence to vessel operators.

Other jobs at Greywing

Frontend Lead
Singapore / Remote
1+ years
Backend Engineer
Singapore / Remote
1+ years
Lead Integrations Architect
Singapore / Remote
Data Science
1+ years
Customer Success Lead
Singapore / Remote
3+ years
Chief of Staff
1+ years