Squire – Company Overview

Squire is a booking and payment platform that connects people with great barbers nationwide. Squire makes it easy to discover and book the best barbers wherever you are, in just a few taps.


Squire is also the premier management platform for barbershops. Using Squire, barbers are able to engage their customers, process bookings and payments and better market their business through Squire’s “barbershop discovery” capabilities. Fully integrated with a point of sale, inventory management and payroll systems, Squire is a one-stop solution for barbershop owners to efficiently operate their business. 


With headquarters in New York and a presence in major cities in the United States and Canada, Squire has quickly become a market leader in technology solutions for the barbershop industry nationwide.


Reid Christian, an investor at Charles River Ventures (CRV) who led the Series B, said that he knew Squire would be a success when he experienced the product at Rust Belt Barbering in Buffalo, New York. Christian compared Squire to a “Venmo-like experience” with transactions. He estimates billions of dollars in men’s grooming spend.


When shops broadly reopen, Squire is in a good, timely spot to be adopted by the masses. For the co-founders, the incoming wave of interest was affirmed a long time ago. For more information, please visit getsquire.com or download the Squire iOS app from the App Store.

The Role: Head of People


Squire is seeking a Head of People who is passionate about recruiting the best talent and building amazing cultures. The ideal candidate has at least five years' experience in HR, building effective processes and organizational structure at a high growth startup. Our Head of People should care deeply about how people work best, how they think, and what motivates their creativity and passion around work.


You will be the steward of our company’s people and talent. You will lead the People function in a fast-growing company, from talent acquisition to onboarding, performance management, career development, and culture and cohesion.

You’ll help bring the best people in the market into the company and propel their performance and careers for years once they’re hired. Building a best-in-class team will take vision, strategy, and organization to pull off. You have a strong understanding of what makes people and organizations think and are a thought partner to the founders on how to bring out the best in their team and bring out the best in each other. You are hands-on - willing to get into the nitty gritty, while also developing the culture and practices for the whole company.



  • Oversee and lead initiatives in Talent Development, Compensation, Benefits, Culture/Engagement, Employee Relations and Facilities Management
  • Help us build and maintain a cohesive global culture (including vision, mission & values)
  • Design and implement Squire’s Diversity and Inclusion strategy, identifying the optimal intersection of D&I goals with our business goals.
  • Use prior experience and creativity to design and build policies, benefits programs, compensation plans, feedback systems, and training programs
  • Help to define our company values and identify ways to live them throughout the company
  • Build and implement programs across recruiting, onboarding, ongoing training, feedback and culture building
  • Provide useful data to help guide decision making, and allow the company to scale effectively and efficiently
  • Provide leadership on people related issues and policies globally across the company
  • Maintaining an environment that promotes healthy communication and handles employee relations issues with the highest degree of empathy and respect


  • 5+ years of experience in People Operations Leadership roles
  • Experience working in an entrepreneurial, growth stage and fast-paced environment, with the ability to lead and adapt in a changing business environment
  • Experience finding, recruiting and managing people, including diverse teams across the globe
  • Exceptional communication & collaboration skills, particularly with people who have different skill sets
  • Show an ability to challenge conventional approaches and a willingness to think creatively
  • An excellent connector who collaborates, problem solves, and can help celebrate wins while learning from mistakes and always keeping the team in mind
  • Brings a focus on data driven decision-making to help influence key strategic decisions


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