Chief of Staff to the 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

Also posted as: VP of Strategic Operations · COO Track · Head of Special Projects · Strategy & Operations Lead

About Rare Candy

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.

The Role

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.

What Success Looks Like

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.

What You'll Do

• 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.

A Day in Your Life at Rare Candy

Morning: you're closing the loop on next week's board deck, pulling the metrics, framing the three decisions that actually need the board's input, and flagging the one number that needs a story.

Midday: a working session with the CEO to pressure-test a partnership you're about to bring across the line, then you're off to run it yourself.

Afternoon: you notice product and ops are drifting on a launch date, so you get the right three people in a room and resolve it before it becomes the CEO's problem. You close the day standing up the operating doc for an initiative that didn't have an owner this morning.

You Might Be a Fit If

• You bring top-tier management consulting, or an equivalent analytical and strategic background, and real operating experience at a high-growth startup. We care far more about your track record of owning hard things than your exact years, though most strong candidates will have around 4 to 8 years behind them.

• You're a finisher. You take ambiguous, half-formed problems and drive them to a clean, complete outcome, not a status update.

• You can produce executive-quality thinking and materials: structure a fuzzy problem, build the board deck, write the memo, make the recommendation.

• You can install a lightweight operating discipline on a fast-moving team without smothering it in process.

• You operate with extreme ownership and a bias to action. You move decisively and have the judgment to make good calls under ambiguity, without hand-holding.

• You're low-ego, high-trust, and discreet. You'll be close to the most sensitive parts of the business, and you handle that like a pro.

• Required signal: you know the trading-card or collector world. You collect, you play, or you've got real fluency in an adjacent collectible community.

What You'll Need to Thrive Here

You'll work in the CEO's orbit, which means priorities shift, context switches are constant, and a lot of your value comes from owning things while they're still ambiguous. You'll have real decision rights on the work you're handed, while the company's direction stays with the CEO, so the people who thrive here are great at extending a founder rather than replacing one.

If you like being the person things route through when they have to get done, this seat is rare.

Why Join Us Now

• Be the trusted right hand to a founder building a category-defining company, with a direct line to every important decision we make.

• Own real scope from day one: the biggest initiatives, the partnerships, the operating rhythm of the whole company.

• This is one of the best seats in the company to learn how a business gets built, and a classic launchpad toward a COO or senior operating path.

• Competitive startup comp and meaningful equity upside.

• Full benefits: health, dental, and vision coverage, 401(k), and a wellness stipend.

• A monthly dogfooding budget to spend on cards, because we hire people who love this hobby.

How to Apply

Apply through our Ashby posting and answer these:

1. Share two examples of ambiguous, high-stakes work you personally drove to a clean outcome. What was messy, what did you own, and what happened?

2. Describe one executive-facing artifact you're proud of: a memo, board materials, an investor update, a decision analysis, an operating doc, or a strategic plan. What made it effective?

3. Tell us about a time execution would have broken without you.

4. What kind of founder or CEO partnership brings out your best work?

5. Required: What trading-card or collector communities do you understand best? Tell us your favorite card, set, format, or collector niche.

Rare Candy is an equal opportunity employer. We celebrate individuality, from Pikachu collectors to Planeswalker pros, and are committed to building an inclusive team.