Chief of Staff, Office of the CEO (San Francisco)

What you will do

You will work extremely closely with, and act as a force multiplier to the CEO: taking on our hardest, most complex, most interdisciplinary problems… to make sure the company runs well and WINS!

You should expect the role to progress as follows:

1. First day: Welcome to the team.

2. Shadowing: Shadow the CEO to understand how the company works, and rapidly accumulate context on our business. You’ll join exec team meetings, external pitches, interviews, product workshops – travel to visit partners and customers, and go very very deep on the most important problems.

3. Solve your first problem: You’ll eventually get bored / feel compelled to dive in and start solving problems. At this stage you take on your first problem and solve it. This could be anything across the business… rebuilding an operational or product process, designing a new product feature, creating a new business line, etc… You’ll take something off the CEO’s plate, and get it done!

4. Take on harder and harder problems: You’ll continue operating as a problem solver across the business, and as you become formidable, the problems will grow more complicated and more impactful. Over time, you may fall in love with a specific part of the company and move into it full‑time, or help us launch a new business line, or even (if / when the time is right) leave to start a company (!)

Why you should NOT join:

• This is an IC role – if you’re looking to manage large teams of people, this role is not for you. If you’re looking to become a very effective problem solver, and learn CEO leadership skills, this could be the right place!

• We plan to hire multiple CoS’in the office of the CEO, if it’s important to you to be the only person in this role at the company, this role is not for you. However, we run our team lean to ensure a very healthy opportunity : people ratio so opportunity will still abound!

• We work very hard – long hours, often on weekends (often on Sundays but never on Saturdays). We understand that winning takes a level of intensity and dedication that others are simply unwilling to.

• Wherever you are weak, this role will push you to grow. You will face unfamiliar problems that demand you learn quickly and improve continuously. Learning and growing is kind of painful, and this role expects you to lean into that discomfort, over and over again.

What we’re looking for:

• Intellectual vitality, you are endlessly curious about how to build a great business, and more broadly, how the worlds of finance and technology work.

• Extremely driven – motivated to build an amazing company and an incredible career, because you love seeing what you’re capable of.

• 5+ years experience doing hard things: this could be through any of a wide range of experiences: consulting, banking, engineering, product, operating, founding a company, taking over a family business, etc…

• Analytical and not afraid of data, but also able to think intuitively.

• You use writing as a tool to think precisely and clarify messy problems.

• Technical. It’s a way of thinking, not a store of knowledge (especially these days).

• Move quickly and take ownership, by default. You feel pain when something isn’t working well and an almost compulsive desire to fix it.

• Humility.

Why Cardless

You’ll join a collaborative, fast‑moving team that values craftsmanship, curiosity, and impact. We’re building products that enable leading brands to offer credit in new ways — and we’re just getting started.

Compensation

This role has an annual starting salary range of $150,000–$235,000 + equity + benefits (see below). Actual compensation is influenced by a wide array of factors including but not limited to skills, experience, and specific work location.

Benefits

We’re headquartered in San Francisco, CA, with a beautiful office in the Financial District. We’re proud to offer our team excellent benefits:

• Meaningful start‑up equity

• 100% health, vision & dental primary coverage

• 75% health, vision & dental dependent coverage

• Catered lunches

• $250/month commuter benefit

• Parental leave

• Team building events & happy hours

• Flexible PTO with a minimum of 15 days off per year

• Apple equipment (unless you’re a PC person, that’s okay too)

• 401k plan

Location

We’re headquartered in San Francisco, CA, with a beautiful office in Jackson Square. We welcome employees who want to work from this office; we offer additional benefits to those who do, and relocation assistance to those who’d like to.