AI-Native Chief of Staff

Why This Role Exists

Our Founder and CEO leads company and product strategy, manages its most important GTM relationships with partners and customers, and drives alignment across the executive team. He also steps in when crises arise. But when he is focused on the top priority, other work can slip: follow-ups go unfinished, research stays in his head, signed partnerships stall, and internal tools that could streamline operations never get built. This role exists to catch those balls and carry them through to completion.

The job is AI-native by default. Our founder and CEO is obsessed with AI and is a heavy user of Claude. We want someone who's even more cracked at it than he is. Engineering already runs on an advanced AI-native SDLC: our engineers ship with agents every day, on a shared team brain that hands work between people and their agents. The rest of the company isn't there yet. Closing that gap is a big part of this job. When the sales team keeps asking the same questions about our capabilities, you build the internal brain that answers them. When the President is curious about the main objections on demo calls, you build an agentic workflow that provides continuous updates and insights.

How this fits with the exec team. You report to the CEO and work daily with our President and the other department heads. You run the CEO's operating system: his follow-through, his research, his special projects, and the cross-department communication that would otherwise die without him.

The CEO's time. The scoreboard for this role is simple: the CEO spends more of his week on thinking about the organization's hardest problems and closing the biggest deals, and less on chasing, researching, and relaying. You default his calendar and his inbox to "handled" and tell him what he actually needs to see.

Think of this seat as an apprenticeship with the CEO. For the first 18 to 24 months, the job is the job: you make the CEO faster, you learn every department from the inside, and you build the tools that make the whole company better. We grow future leaders from this seat on purpose, and the step up comes from owning outcomes, not from a countdown. When you've proven it and the company has a gap worth filling with you, that's when it happens. We're not hiring a career chief of staff. We're hiring someone we'd trust to run something big one day.

What You'll Own

Cross-department alignment and follow-through. You help the CEO write the weekly Companywide Alignment memo: you pull updates from every department, draft from the week's meetings, and get it to him mostly done. Once it's out, every ask in it has an owner, a date, and a written confirmation. You track them and you chase them. When something starts slipping, your first move is to help: unblock a dependency, pull the data they need, or build the automation that frees up their week. If it's still slipping, you escalate to the CEO before it's late, not after.

Market and GTM research. The kind of work the CEO has been doing himself for the strategy memos: market sizing by segment, competitor teardowns (product, pricing, positioning, what they just shipped), platform moves and what they mean for our merchants, etc. You pull from merchant communities, competitor products you actually use, public filings, and our own data.

Partnerships, from first call to live. You join the CEO on partnership calls, and you bring a point of view: is this worth doing given everything else on our plate, and what would it take to make it real? Talking us out of a shiny partnership that doesn't fit is as valuable as closing a good one. When we say yes, you run the cross-department plan that gets it live: legal review through the President, a spec from product, an integration slot from engineering, a rollout to merchants with client success, and the announcement with marketing. Every partnership gets a number, an owner in each department, and a next step, and nobody is left waiting on someone else.

The big merchants the CEO closes. The CEO personally works our largest prospects, and the handoff from his close to a live, scaling merchant is where things can slip. You're the second pair of eyes on every deal he's involved in. You join the calls, pull every commitment we made from the call notes that same day, and make sure client success, implementation, and payments deliver on it: onboarding on schedule, processing approved, backup accounts warmed up, the first campaigns live, and the merchant ramping the way we said they would. If something is stuck, you know before the merchant does and you get the right person moving. Client success owns the relationship. You make sure nothing falls through the gap between the CEO's handshake and the merchant's first big month.

Special projects that need a bullet train. When something needs to go from idea to live in days, you run it end to end. Here are a few examples:

• An internal Phoenix brain. Any sales or operations team member asks a question and gets a real answer: Can we move subscribers from one gateway to another, and how? What percent of our portfolio is VIP membership vs. autoship? What's the current expected delivery date for the AI-native checkout builder? Which promising merchants aren't activating and why? Is this a merchant that we would accept on Adyen? Engineering has started a Team Brain for code and context; you extend that thinking to the rest of the company, built on our CRM, our docs, our roadmap, and our meeting transcripts.
• The CEO's agent team. The CEO runs much of his week through his own set of AI agents, each built for a different kind of work: strategy, project management, company-wide insights and analytics, and more. What makes them good is context: how each agent's knowledge, decision trees, and playbooks are organized so it knows how to think in its situation, plus the routing that sends each question to the right one. You help him push that further. You structure each agent's context, sharpen the decision logic for the situations it handles, and build the loop so every agent gets better from its own sessions and corrections. The goal is a CEO who can trust his agents with more of his thinking, not just his tasks. Then you turn it into the template every department head runs on.

You're also the AI coach for every department head. Our leaders are excellent operators, and most of them are earlier on the AI curve than engineering. Your job is to make that curve feel easy, not intimidating. You sit with each of them, find the one workflow eating their week, build it together, and show them how to run and change it themselves. Small wins first, then bigger ones. **Success is every department head shipping their own automations within a few months, not you building everything for them.

AI before headcount.** When a department head wants to add a person, you're in the conversation before the role opens. You break the job down task by task, figure out how much of it an agent could do, and build that part with the department head. Sometimes the answer is still to hire, and then you make sure the new person starts AI-native from day one. Sometimes the answer is one great hire instead of three. You're not a gate on hiring; the department head and the President still make the call. You make sure we've asked whether AI could do the job first.

What Success Looks Like in 90 Days

Day 30. You know our ICP, our product, our competitors, the market, and our team at ground level. You've used the platform the way a merchant does, sat in every department meeting, and can name what each department head is driving from memory. You've taken over cross-department communication, most of the CEO's follow-ups, project tracking, and monitoring, and a big chunk of his admin. Things that used to wait on the CEO now move without him.

Day 60. You're automating real workflows. The Phoenix brain is live and cutting the communication tax: the team gets answers in seconds instead of pinging three people and waiting a day. Several team members outside engineering are building with AI because you sat with them. And at least one role we planned to hire never opened, because your automation does the job.

Day 90. The CEO is getting significant time back every week, from the agents you built for him and the operations you took off his plate. When his attention gets pulled into one fire, nothing else drops. Every department head will tell you they're moving faster because of you. And on the decisions that matter, you bring insight from deep research and command of the details, and the CEO wants your research or analysis before he makes the call.

Who You Are

• An emerging leader. You have strong business acumen and can operate as a force multiplier bringing organization, accountability, and follow-through to priorities across the business.
• The complement to the CEO. Our CEO is a visionary and a deal maker. He thinks in big concepts, gets his energy from closing, and he'll be the first to tell you he loses dopamine once a deal turns into activation and operations. You're wired for the other half. You love the details, you live in the weeds, and you get your energy from taking what he started and making it real. Where he's high level, you're precise. Where he moves on, you follow through.
• AI-native by default. You build with modern AI tools every day. You've shipped working automations, agents, or internal tools that real people use. You can name the last three things you shipped with an agent and what they replaced. If you don't know how to do something, your first move is to build it, not to ask who owns it.
• Obsessed with your career and learning. You've done more than your resume should allow, and you want the reps that only a seat next to a founder gives you. You're here for the hardest and most informative stretch of your career, on purpose.
• A missile, not a passenger. You operate with a lot of autonomy and solve problems instead of escalating them. You don't bring us problems; you bring solutions and the resources you need to execute.
• A clear, fast writer and a careful thinker. Research turns into a tight memo in 48 hours, with the numbers checked and the sources named. You can hold your own in a strategy conversation with the exec team because your opinions come from the work.
• Confident with people more senior than you. You're comfortable working alongside people with a lot more experience than you, and you still speak up. You disagree respectfully, push a department head for a date, and make them glad you did. You communicate clearly in writing and in the room, and you can hold your own with our senior leadership and with executives at our partners and our biggest merchants. No ego, no politics, no back channels.
• Startup-forged. You've thrived in fast, resource-constrained, high-intensity environments in the last few years, or you've built something of your own.
• No tolerance for mediocrity. The people who thrive here hold themselves and others to an extremely high standard with no exceptions. We're here to build a generational company.

Huge Plus

• You live in South Florida or can travel there consistently, so you can work very closely with the founder and CEO.
• You've run a DTC or direct response ecommerce business so you understand the market that we play in.
• You've been a founder, an early operator who owned the outcome, or a chief of staff / founder's office at a rapidly scaling startup.