Our website is best viewed using a modern browser like Chrome, Firefoxor Microsoft Edge.

Find your dream job at a Trinity portfolio company.





Sales Representative



Sales & Business Development
Austin, TX, USA
Posted on Tuesday, September 12, 2023


SQUIRE is the world’s leading and fastest-growing software technology platform for barbershops, a hundred-billion-dollar global industry. We provide a one-stop solution that helps small business entrepreneurs run and grow their businesses. SQUIRE is also the premiere booking engine that connects people with great barbers nationwide. We make it easy to discover and book the best barbers wherever you are, in just a few taps.

With headquarters in New York, NY and a presence in major cities in the United States and the U.K., SQUIRE has quickly become the market leader in technology solutions for the barbershop industry. We are a Series D company and have raised over $165M to date.

For more information, check us out online or download the SQUIRE app from the App or Play Store.


We believe in 3 key traits that create the foundation for success in all sales roles within our team:

  • Coachability
    • The barber shop industry is complex and constantly changing. We are looking for folks that are not only open to being coached to success, but are able to take feedback and implement it quickly. The attitude of “feedback is a gift” goes a long way!
  • Work Ethic
    • We are big believers in ‘‘talent is overrated”. Are you familiar with Malcolm Gladwell's “10,000-hour rule"? He asserted that the key to achieving true expertise in any skill is simply a matter of practicing, albeit in the correct way, for at least 10,000 hours. That's a lot of hours. Do you have the hunger and desire to get to them quicker than anyone else? Awesome, so do we.
  • Attitude
    • Sales is full of setbacks and there will be more deals that don’t go your way than close. Feeling comfortable failing and understanding that “failure is a stepping stone on the path to success” is what is needed to be successful in any sales role, especially sales in a startup environment. We are constantly learning from mistakes, iterating on processes and redefining the 'how'. We are looking for positive people to add to our team, who believe that it isn’t success that leads to happiness, it’s happiness that leads to success.

Those are our top 3. They are the absolute requirements. Still with us? Read on...


We are seeking a motivated and dynamic Sales Representative to join our team and focus on selling our product to barbershop owners. As a Sales Rep, you will be responsible for the full sales cycle, prospecting, qualifying, and nurturing new leads, developing relationships with brokers, running product demonstrations, negotiating and closing business.

Hours & Location

This is a full time role, Monday-Friday 8:30am-5pm.
This is an ‘in-office’ role in Austin, TX.

Job Duties & Responsibilities

Direct Sales Activity

  • Identify, prospect and qualify barbershop owners through various channels such as phone calls, email, social media, and events.
  • Manage a robust sales pipeline and follow up with prospective customers to drive to the close.
  • Provide brand awareness, insights, and success stories with prospective customers to help articulate a customized value proposition.
  • Document calls, emails, and other relevant sales activity inside Salesforce.
  • Partner with internal team members from Sales, Product, and/or Client Success to support deal closure.

Product Demos

  • Schedule and give product demos to prospective customers showcasing key features and functionality.
  • Understand prospective customers, their business, their pain points, and showcase how our software makes an impact and adds value.
  • Work closely with our Product and Customer Success teams to uniquely position our product to shop owners.
  • Identify key stakeholders and schedule follow-up demos to shorten the sales cycle.
  • Attend trade shows and events as required to represent and promote SQUIRE.

Contract Negotiation

  • Negotiate new customer contracts, obtaining appropriate approvals for any non-standard terms or conditions.
  • Defend standard net payment terms and invoicing schedule.

The duties and responsibilities outlined above are not a comprehensive list and additional tasks may be assigned from time to time based on business needs.

Requirements / Qualifications

  • Must be willing to work in-office in Downtown Austin area Mon-Fri
  • 2+ years sales experience in full-cycle sales
  • An outbound/hunting pro
  • Experience demonstrating complex software live over Zoom or similar tool
  • Excellent interpersonal skills
  • Proficiency with Salesforce preferred, ability to manage entire pipeline
  • Energetic, upbeat, tenacious team player with excellent verbal and written communications skills
  • Strong organizational skills, detail and process-oriented
  • Ability to travel as needed (approximately 10% annually)

What We Offer

  • Annual base salary of $65,000 + annual incentive comp target of $45,000 (with an uncapped commission plan!)
  • New hire stock grant
  • 100% employer paid medical/dental/vision insurance for you and your dependents
  • 401K plan with automatic company contribution of 4% of eligible earnings - we contribute regardless of whether you do!
  • Generous PTO and Parental Leave policies

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 policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.