Business Operations Associate at Whippy
Los Angeles, hybrid with our CEO | Full time | Early start: we run on East Coast time

Whippy is the AI native platform for business communication: 1,000+ customers, bootstrapped, profitable, category leader in staffing and HR with new verticals opening behind it. Our CEO is a former professional poker player who built and sold a company before this one. Right now, he is also personally the company's router: billing, vendor invoices, support triage, contract prep, recruiting coordination, and meeting logistics all flow through his inbox.

Your job is to take that entire layer off his plate, run it better than he did, and earn your way into the work that sits closest to him. You will learn more about how a real business actually works in twelve months here than in three years anywhere else, because you will be inside every decision, not reading about it in a deck.

How we work

Bootstrapped and profitable, so revenue is the strategy. We run on our customers' clock. They are East Coast; we start early. No task is above or beneath anyone here, including the CEO, who still cold calls. AI first: we expect you to use AI to automate your own work, then everyone else's. Speed over polish. Results over activity.

What you will own first

Billing and collections. Monitor Stripe for failed payments and overdue invoices, chase them to resolution, reconcile checks. The CEO should never type the word "Paid" again.
Contract and system alignment. Keep HubSpot, PandaDoc, Stripe, and our internal database in sync so what a customer signed, what they use, and what they pay always match. Today these drift and revenue leaks. You stop that.
Upgrade and renewal execution. Deals close, you prepare the paperwork, update billing, send the recap. Leadership approves; you execute.
Accounts payable and customer billing support. Vendor invoices processed on schedule, customer requests handled same day.

What you will own by day 90

Inbound routing. Everything that lands with the CEO gets resolved or routed by you, with follow through until closed.
Recruiting operations. Applicant responses, sourcing tools, interview scheduling, and pipeline tracking across multiple open roles.
CEO operations. Meeting prep, follow up tracking from calls, and the recurring tasks that currently live in his head.

What this grows into

Once the operational layer runs without reminders, you graduate into the work most companies reserve for MBAs and consultants:

New market research. We are expanding beyond staffing. You research the industries, size the opportunities, and build the briefs that decide where we go next.
Pricing and deal modeling. Model pricing scenarios for enterprise deals, partner revenue shares, and new products.
Partnership and channel research. Find the ecosystems where our next hundred customers already live.
Special projects. Whatever needs analyzed, scoped, or figured out, you are the CEO's first call.

We will not pretend this is the day one job. The strategic work is earned by making the operational work disappear. But it is real, it is the path, and your analysis will change actual company decisions, not die in a slide deck.

What success looks like

First 30 days: zero overdue invoices without an active follow up, and the three system reconciliation is current.
First 90 days: you own the routing layer and recruiting coordination runs without reminders.
Year one: the operational layer runs without you being asked, and you have shipped at least two strategic projects that changed a company decision.

Who succeeds here

You are one to three years out of school and can point to concrete evidence you outwork and outthink your peers: you ran something, built something, worked through school, competed at something seriously, or were the person your last team could not function without. You are organized to a fault and nothing you own needs to be asked about twice. You write clean, professional English fast. You are fluent with spreadsheets and already use AI tools to work faster. And you have judgment: half this job is defined tasks, the other half is noticing what needs doing before anyone assigns it.

Experience with Stripe, HubSpot, or billing is a plus, not a requirement. We can teach tools. We cannot teach ownership.

This is not for you if

You think grunt work is beneath you. Billing is week one, and it is how you earn everything after it.
You need detailed instructions for every task.
You want a job description that never changes. This role expands every month.
You are looking for a remote job. This role works alongside our CEO in Los Angeles.

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