whippy - Head of Operations

• Five areas. You run all of them personally at first, then you hire and build the systems that run them after you. • 1. 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. • 2. 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. • 3. 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. • 4. 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. • 5. 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 • 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. • What I'm looking for • 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 • This is not for you if • 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