Head of Operations

Whippy

4d•Remote

About The Position

Whippy is seeking a Head of Operations to take ownership of all non-selling, non-product building, and non-customer-serving aspects of the company. This role involves building and leading the team responsible for these operations. The company is bootstrapped, profitable, and a leader in AI communication for staffing, with over 1,000 customers. The CEO currently handles many back-office functions, which is no longer sustainable. The Head of Operations will learn each operational area by doing it themselves, document processes for others to follow, and hire an Operations Associate to manage these tasks. The goal is for the operational layer of the company to run independently of the CEO within a year, with the Head of Operations leading it. The role offers significant growth potential, moving into strategic areas like company operating cadence, partner strategy, pricing, and market expansion.

Requirements

Experience building an operations function from scratch.
Proven experience with billing, collections, contracts, and systems management.
Experience managing people and building processes that others can run independently.
Experience handling significant matters with external parties (partners, vendors, customers).
Willingness to be hands-on for the first six months.
Strong organizational skills.
Clear written communication skills.
Comfortable being direct with a founder.
Fluent written and spoken English.
Ability to work US Eastern hours.
Experience at a SaaS company, preferably one selling to operators.
Staffing or HR tech experience is a plus.

Nice To Haves

Experience in staffing or HR tech.

Responsibilities

Own and personally manage revenue operations, including billing, collections, and payments through Stripe and HubSpot.
Oversee the quote-to-cash process, including automation projects.
Manage sales operations for Account Executives (AEs), including pipeline and forecast reporting, commission calculation, and deal desk support.
Handle account changes such as upgrades, downgrades, churn, and cross-sells across all systems.
Manage contracts, including order forms, MSAs, NDAs, and partner agreements.
Oversee vendor and SaaS management, including renewals, usage audits, seat counts, and costs.
Ensure alignment between customer contracts, usage, and payments.
Manage partner administration, including revenue share calculation and payment for ATS partners.
Maintain partner records, pipeline, and co-marketing logistics in HubSpot.
Lead people and recruiting operations, managing the recruiting process from sourcing to scheduling, excluding final interviews.
Manage offers, onboarding, offboarding, PTO, and expense policies.
Oversee the review cadence.
Hire and manage an Operations Associate to take on initial operational tasks.
Develop and maintain documentation for all processes.
Manage security and data requirements for enterprise customers and work towards SOC 2 readiness.
Control access, manage offboarding security, and implement tooling to protect company data and finances.
Transition to strategic responsibilities such as company operating cadence, partner strategy, pricing, and deal modeling after mastering initial operational areas.