Chief of Staff

New York
About Otis
At Otis, we turn aficionados into shareholders. We believe in transparency, liquidity, and trusting your own gut. We're democratizing an otherwise closed market and making alternative assets accessible. Invest in the things that you value, and whose value you understand, for as little as $10 and build a portfolio better suited to a museum than a stock ticker.

Our Culture
We have a saying here: “we design our culture like we design the product.” Culture is the most important foundation for a successful company. A great culture provides the context for people to deliver their best work. Our goal is to find the fastest way to win. Our culture is designed to allow us to achieve this (read more).

Your responsibility is simple: creatively solve any problem that gets thrown your way w/ relentless execution. In exchange, you'll get front row seats taking a company from 0 to 1. And, more importantly, gain the skills, network and experience to accelerate your career.

You'll work directly with the CEO and we'll carve out a role that fits your strengths and passions. You'll get to wear lots of hats: company strategy, fundraising, business operations, marketing, sales, hiring, product, etc - whatever is the top priority. We'll divide and conquer.

Your "tour of duty" will be for 24 months. Once your mission is done, we'll talk through what you want to do next in your career. It can be moving to a new role within a company, or even starting your own. We'll be supportive and help you land on your feet.

Some CoS alumni who worked with me include: Peter Boyce who is now a Principal at General Catalyst ($1B+ fund), Stephen Yang now Growth Product Lead at GoEuro ($146M raised) & TT Nguyen Duc who is a VC at Pearson Affordable Learning.

Who's ideal for this role? Mission-driven. Driven by disrupting the status quo. Collaborative. Resourceful. Curious. Has a growth mindset. Not scared to roll your sleeves up and GSD. First principles thinker.

How to Apply
1) Personal Deck: include a) why you want to join Otis; b) biggest accomplishments, c) strengths & weaknesses and d) anything else you want to include that showcases yourself (no more than 8 slides)
2) Written Memo - pick an asset over $1M (not art) that we should invest in on the platform (no more than 2 pages)

We expect the process to be finished by end of March and candidates should be able to start in April or May.
March 8: Final applications due by 5pm EST
Week of March 10th: Phone interviews
Week of March 17th: In-person meetings
Week of March 24th: Chief of Staff selected

Salary: $65K - $105K
Equity: 0.50% - 1.50%

- Medical, Dental, and Vision coverage 
- 401K 
- Unlimited vacation policy (with 10-day minimum) 
- WFH Tuesday's
- Pre-tax commuter benefits
- Quarterly company outings

What You'll Do

    • Special Projects: An extra set of hands to help with strategic priorities on anything from Product to Growth
    • Company Strategy: A strategic advisor and confidant (a highly trusted person with whom to discuss and pressure-test ideas);
    • Business Operations: An organizer to help manage a picture of the priorities, projects, decisions, and actions that should be in the brain space of the CEO

Who You Are

    • Experience - 2+ years experience working at a startup (ops & strategy), consulting, or investment bank
    • Super Organizer — Because a CoS is often brought in to help bring order to things, the individual needs to be a methodical organizer.
    • Strategic Thinker — The CoS needs to be able to see the big picture of things. A strategic mindset helps align detailed work to the big picture strategy, as well as evaluate what is urgent versus important.
    • GSD Reputation — The Principal and the leadership team need to know that responsibilities or tasks that fall to the CoS are guaranteed to get done. The CoS should have a reputation for never dropping the ball.
    • Trusted Operator — The CoS is often exposed to sensitive or confidential information in the normal course of executing the role. Consequently, the person in that role has to innately appreciate how to manage such information in confidence and with discretion.
    • Expert Facilitator—Finally, a day-to-day part of being a CoS requires managing conversations, synthesizing multiple points of view, and aligning on direction…all in an impartial and professional way.
Who You'll Work With
- Michael Karnjanaprakorn (CEO) who was formerly the CEO/founder of Skillshare
- Tye Wang (Head of Engineering) who was a Lead Architect at Venmo
- James Gilligan (Head of Operations) who ran operations at CommonBond and helped originate $1.5B

Transparent Compensation
We don’t believe that better negotiators necessarily make better employees. Inspired by Buffer’s salary transparency, every employee can see their current salary, the salary levels for their team, and what each level’s salary increase would amount to in the future. This allows us to offer equal pay to all employees.

Diversity & Inclusion
We are committed to building a culture where diverse thoughts are both welcomed and rewarded.