Head of Operations (Remote, LATAM or US)

Hi, I'm David, CEO and co-founder of Whippy. I'm hiring a Head of Operations to own everything in this company that is not selling, building product, or serving customers, and to build the team that runs it.

Why I'm hiring

Whippy is bootstrapped, profitable, and the category leader in AI communication for staffing, with over 1,000 customers and new industries opening behind it. We got here with a small team and a CEO who personally runs billing, contracts, payments, HubSpot, partner administration, recruiting, and most of the back office. That worked at 300 customers. It does not work at 1,000, and it will not work where we are going.

My time needs to go to enterprise customers, new partnerships, new industries, and the hires that change the company. Everything else that routes through me today needs an owner.

The thesis for this role is simple. Learn each piece by doing it yourself. Document it so someone else can run it. Hire an Operations Associate to take it from you. Move up to the next piece. A year from now, the operational layer of this company should run without me being asked a question, and you should be the one running it.

What you will own

Five areas. You run all of them personally at first, then you hire and build the systems that run them after you.

Revenue operations

Billing, collections, and payments across Stripe and HubSpot. Quote to cash from signed order form to first invoice, including the automation project underway with our RevOps consultant. Sales operations for our AEs: pipeline and forecast reporting, commission calculation, deal desk support within guardrails I set, and the HubSpot setup our reps actually use. Account changes, meaning upgrades, downgrades, churn, and cross sells reflected correctly in every system.

Contracts and vendors

Contracts on our templates: order forms, MSAs, NDAs, partner agreements, with a short list of what comes to me. Vendor and SaaS management: renewals, usage audits, seat counts, and cost. Making sure what a customer signed, what they use, and what they pay always match.

Partner administration

Rev share calculation and payment for our ATS partners. Partner records, pipeline, and co marketing logistics in HubSpot. Over time, joining and then running our standing partner check ins once you know their business as well as I do.

People and recruiting operations

The recruiting process for every open role except final interviews, which stay with me and the hiring manager: sourcing, outreach, scheduling, pipeline in Ashby. Offers, Deel, onboarding and offboarding, PTO and expense policies, review cadence. Hiring and managing the Operations Associate who takes the first layer of this work from you.

Systems, process, and compliance

Documentation for every process you touch, written so a junior person can run it. The security and data packet enterprise customers ask for in vendor review, and SOC 2 readiness when we need it. Access control, offboarding security, and the tooling that keeps us from leaking money or data.

What this grows into

Once the five areas run without reminders, you move toward the work that sits closest to me: the operating cadence of the company, partner strategy and enablement, pricing and deal modeling, and research on the industries we expand into next. I will not pretend that is the day one job. It is earned by making the day one job disappear. But the ceiling here is high, and the people who make the operational layer disappear are the ones who end up running more of the company.

What success looks like

First 30 days: you have personally run every billing, payment, and contract process at least once and written down what is broken

First 90 days: zero overdue invoices without active follow up, systems reconciled, and I have not touched Stripe or a contract template

First six months: you have hired the Operations Associate, they work off documentation you wrote, and partner administration, recruiting, and people ops run through you

Year one: the operational layer runs without me, and you have shipped work that changed a company decision