[Hiring] Head of Operations @Whippy

Role Description

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.

Whippy is bootstrapped, profitable, and the category leader in AI communication for staffing, with over 1,000 customers and new industries opening behind it. 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

• Revenue operations:
  • Billing, collections, and payments across Stripe and HubSpot.
  • Quote to cash from signed order form to first invoice.
  • Sales operations for our AEs: pipeline and forecast reporting, commission calculation, deal desk support.
  • Account changes: upgrades, downgrades, churn, and cross sells reflected correctly in every system.
• Contracts and vendors:
  • Contracts on our templates: order forms, MSAs, NDAs, partner agreements.
  • Vendor and SaaS management: renewals, usage audits, seat counts, and cost.
  • Ensuring customer agreements match usage and payment.
• Partner administration:
  • Rev share calculation and payment for our ATS partners.
  • Partner records, pipeline, and co-marketing logistics in HubSpot.
  • Joining and running our standing partner check-ins.
• People and recruiting operations:
  • The recruiting process for every open role except final interviews.
  • Offers, Deel, onboarding and offboarding, PTO and expense policies.
  • Hiring and managing the Operations Associate.
• Systems, process, and compliance:
  • Documentation for every process you touch.
  • Security and data packet for enterprise customers.
  • Access control, offboarding security, and tooling to prevent leaks.

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.

What success looks like

• First 30 days: You have personally run every billing, payment, and contract process at least once and documented 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.

How we work

• 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.
• 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.

What I'm looking for

• You have built an operations function from scratch.
• You have managed people and built a process that others ran without you.
• You have handled important matters with external parties.
• You are willing to be hands-on for the first six months.
• Organized to a fault, clear in writing, and comfortable being direct.
• Fluent written and spoken English, and able to work US Eastern hours.
• Experience at a SaaS company, ideally one that sells to operators.

This is not for you if

• You think the operational work is beneath the title.
• You want a defined scope that does not change.
• You prefer to coordinate rather than own.

About Whippy

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. 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.

Location

Remote, open to candidates in Latin America or the United States. Preference for people near where the company operates: Los Angeles or New York, or Buenos Aires.

Hiring process

• You apply and I review it myself.
• A 45-minute call with me.
• A take-home assignment to fix and document a process.
• A 30-minute call with Jack, our CTO.
• References, including someone who reported to you.