Head of Operations

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.

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

1. →

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.

• 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

Bootstrapped and profitable, so revenue is the strategy. Our customers are East Coast, so we start early. No task is above or beneath anyone here, including me, and I still cold call. We use AI to move fast, but we own our work and verify every fact. Speed over polish. Results over activity. You will always know where you stand with me.

• You have built an operations function from scratch, not inherited one. You know what billing, collections, contracts, and systems look like when they are done right because you have done it

• You have managed people and built a process that other people then ran without you

• You have sat across from an external party, a partner, a vendor, a customer, and handled something that mattered

• You are willing to be hands on for the first six months. If you need a team on day one, this is not the role

• Organized to a fault, clear in writing, and comfortable being direct with a founder

• Fluent written and spoken English, and able to work US Eastern hours

• Experience at a SaaS company, ideally one that sells to operators rather than to tech companies. Staffing or HR tech is a plus, not a requirement

• You think the operational work is beneath the title. It is the first six months and how you earn everything after

• You want a defined scope that does not change. This role expands every quarter

• You prefer to coordinate rather than own. I need someone who closes things, not someone who tracks them

Whippy is a communication, automation, and AI agent platform. You reach customers across calls, texts, and email at scale, with every conversation in one shared inbox. Replies get assigned to a teammate, handled by an AI agent, or carried forward by an automation, and the data flows back into your systems in the format you need. It cuts the repetitive work and frees teams for the human work that drives revenue.

We're industry agnostic, with our biggest wins in staffing, healthcare, and other in person businesses going through digital transformation. We're bootstrapped, profitable, and growing fast, with over 1,000 businesses using Whippy worldwide.

Whippy was founded in 2021 by me and our CTO, Jack Kennedy. Jack is an engineering machine and a marathon runner. I started BloomNation in 2011 after winning $27,205 in a poker tournament, grew it into a platform generating billions in sales for florists, then left to build something bigger with Jack.

Remote, open to candidates in Latin America or the United States. Preference for people near where the company actually operates: Los Angeles or New York, where I spend most of my time, or Buenos Aires, where our CS and operations team is based and we have a WeWork office. US Eastern hours (so yes if you are West Coast expect to be an early riser). Full English fluency required.

1. You apply and I review it myself

2. A 45 minute call with me

3. A take home: I give you a real snapshot of how one process runs today, and you come back with how you would fix it, document it, and hand it off. You present it to me on a 45 minute call

4. A 30 minute call with Jack, our CTO

5. References, including someone who reported to you