Chief of Staff to CEO

Location: NYC preferred but remote possible. We work in person when we can, and you’ll travel to wherever the work is.

Compensation: Competitive startup comp and meaningful equity upside

Department: Executive / Operations

Reports to: CEO

Rare Candy is revolutionizing the $25 billion trading‑card industry as the only community marketplace 100% dedicated to TCGs. Collectors use our AI‑powered card scanner, data‑rich collection tools, and jaw‑dropping drops to buy, sell, rip, and showcase Pokémon, MTG, Lorcana, One Piece, and more. We’ve hit 10x revenue growth over the last 6 months, the business is highly profitable, and we’re building the team to take this from a great product to a category‑defining one.

We’re a 10‑person team moving fast and looking for the next set of TCG‑obsessed rock stars to join our team.

Here’s the test for this role: where does execution break when the founder steps away for two days? Your job is to make sure the answer is ‘it doesn’t.’

We’re hiring a Chief of Staff to work directly with the CEO on the highest‑priority strategic and operational work across the company. You’ll own the work that falls between functions: cross‑functional initiatives, big bets, and the operating rhythm, so the company works on the right problems in the right order, with clear decisions and real follow‑through.

This is a senior operating role, not an administrative one. You won’t manage calendars or book travel. You’ll take fully formed priorities off the CEO’s plate and run them to completion: standing up new initiatives from zero, driving major projects across the line, owning big partnerships, and preparing for the moments that matter most, like board meetings and investor communications.

You own assigned CEO priorities end‑to‑end and make the in‑flight calls. On company strategy and major decisions, you provide sharp recommendations, and the CEO makes the final call.

If you’ve got the analytical horsepower of top‑tier consulting and the scars of having actually operated inside a startup, and you want to be the trusted right‑hand to a founder building something fast, this is the role.

First 30 days:
You take one live, high‑stakes workstream the CEO owns today – a new business line launch, or a stalled cross‑functional initiative – and run it to a clean finish with less oversight each week. Along the way, you map where execution breaks when the CEO steps away and start closing those gaps.

First few months:
The CEO’s recurring obligations, including board prep, investor comms, and the leadership operating cadence, increasingly run on rails without the CEO drafting them. You’ve taken ownership of at least one major initiative end‑to‑end.

By the end of year one, you’ve given the CEO meaningful time back. You’ve shipped six zero‑to‑one initiatives and several major partnerships under your ownership. The company’s operating rhythm is tighter and no longer depends on the founder to function, and cross‑functional work across product, ops, and growth stays aligned without routing through the CEO.

• Own the founder’s top priorities end‑to‑end: take major initiatives and run them to completion, making the in‑flight calls so the CEO doesn’t have to.

• Stand up new things from zero: the projects that don’t have an owner yet. You bring the structure and the follow‑through.

• Install operating cadence: tighten the leadership meeting, the planning rhythm, and the follow‑through, so the company stays aligned. Just enough process to move fast and reliably, never bureaucracy on a small team.

• Own big partnerships: carry significant external relationships and represent the company and the CEO credibly to partners and stakeholders.

• Prep the moments that matter: build board decks, investor updates, and the structured analysis behind the CEO’s biggest decisions. Consulting‑grade materials, startup‑grade speed.

• Handle the sensitive stuff: you’ll be close to the raise, the board, and the numbers. Discretion and judgment are the job.

Morning: you’re closing the loop on next week’s board deck, pulling the metrics, framing the three decisions…