[Hiring] Chief Retrograde Officer @SQUIRE

Role Description

SQUIRE is looking for a Chief Retrograde Officer (CRO) to keep our teams, launches, and group chats running smoothly when the planets don't cooperate.

• Own the company-wide Mercury Retrograde Readiness Plan, from the first shadow period to the final all-clear.
• Review every product launch, contract, and "quick send" email for cosmic risk before it ships.
• Maintain the Retrograde Calendar and brief leadership at least two weeks before each cycle begins.
• Lead the Cross-Functional Backup Council, making sure every critical file, password, and Slack thread has a backup.
• Run post-retrograde retrospectives to separate real incidents from "it was probably the planets."
• Partner with People Ops on a Retrograde Wellness Program, including optional calm-down hours and snack stipends.
• Serve as the executive voice of reason when someone wants to sign a major deal during an eclipse.

Qualifications

• 8+ years leading operations, risk, or business continuity at a fast-growing company.
• Deep working knowledge of planetary cycles, and the humility to admit when the data says otherwise.
• A calm, steady presence when launch day, a server outage, and a full moon happen at the same time.
• Strong cross-functional communication skills, especially the ability to explain "no, we really shouldn't send that today."
• Experience building playbooks and checklists that busy teams actually follow.
• A sense of humor, and a willingness to take the work seriously without taking yourself too seriously.
• Bonus: a backup of your backups.

Company Description

SQUIRE is the leading business management platform built specifically for barbers and barbershops. Our platform brings scheduling, payments, marketing, payroll, and business insights together in one place, helping barbers and shop owners run smarter businesses and create great experiences for their customers.

Backed by Y Combinator, ICONIQ Capital, and Tiger Global, we’re building the tools for an industry that deserves technology designed around its needs.

We believe great work happens when people have the trust, autonomy, and support to make things happen. We're a team that values collaboration, moves with purpose, and genuinely cares about the work we do and the people we do it for.

Hiring Process

• Interview Accommodations: SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities.
• Equal Employment Opportunity: SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type.
• Pay Transparency Nondiscrimination Provision: SQUIRE will not discharge or discriminate against employees or applicants for inquiring about or discussing pay.
• AI in the Hiring Process: SQUIRE may use AI tools to support parts of the hiring process, but all final hiring decisions are made by humans.