Chief retrograde officer

SQUIRE is the leading business management platform built specifically for barbers and barbershops. Barbering is more than a haircut. It’s craft, culture, entrepreneurship, and community and we get to build the technology that helps the people behind it do what they do best.

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. We also make it easier for consumers to discover great barbers to book their next fresh cut. Backed by Y Combinator, ICONIQ Capital, and Tiger Global, we’re building the tools for an industry that deserves technology designed around its needs.

That same passion for the industry carries into how we work. 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. We're proud of what we're building and even prouder of who we're building it for.

About the role

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.

What you'll do

• 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.

What you'll bring

• 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.

A few things to know about our hiring process:

We are committed to making hiring at SQUIRE fair, thoughtful, and accessible for every candidate. Below are a few important details about our hiring practices and policies.

Interview Accommodations

SQUIRE is committed to working with and providing reasonable assistance to individuals with physical and mental disabilities. If you are an individual with a disability requiring an accommodation to apply for an open position, please email your request to recruiting@getsquire.com and someone on our team will respond to you shortly.

Equal Employment Opportunity

SQUIRE provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

Pay Transparency Nondiscrimination Provision

SQUIRE will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information.

AI in the Hiring Process

SQUIRE may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment with all final hiring decisions ultimately made by humans. If you would like more information about how your data is processed, please contact us.