Payments Operations Specialist at Squire (Remote)

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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 and a presence in major cities in the United States, U.K., and Canada, Squire has quickly become a market leader in technology solutions for the barbershop industry.

Squire is currently a Series D company and has raised over $165M to date.

For more information, please visit or download the Squire app from the App or Play Store.


The Payment Operations Analyst provides data-backed forecasts, payment reconciliation and performance insights for sub-merchant payments and facilitating continuous business improvements. The Analyst partners with various teams across the organization such as Compliance, Settlement, Finance, Fraud analysis, Onboarding and Customer Success, to optimize current customer payment practices and implement new initiatives. The analyst will define problems, collect data, establish facts, and draw valid conclusions. The analyst will work with vendors to test, and implement solutions and data conversions for payment products. An important objective of the group is to advance our ability to manage and control risk and this role contributes to that objective through ongoing compliance with applicable rules and regulations.


This position reports to the Director, Credit Risk 


  • Lead domestic assessment, internal communication, and ongoing monitoring of the impacts resulting from changes in consumer payment acceptance rules and regulations
  • Identify and document compliance gaps and suggest remediation action items for implementation, in collaboration with the lines of business and external stakeholders
  • Lead domestic coordination and execution of our due diligence process for prospective business partners, and periodic reassessments of existing partners, in consumer payments
  • Document and maintain the payment acceptance architecture and compliance status for SQUIRE’s lines of business to aid in the assessment of new rules and regulations and ongoing compliance
  • Detect fraud trends by analyzing data and recommending strategies to reduce fraud losses and reduce chargebacks
  • Reach out to customers when suspicious activity is detected and/or rejected payments to conduct an interview around the activity
  • Assist with payment optimization, daily settlement reconciliation and reporting of payment trends
  • Through analysis, assist in the evaluation and identification of opportunities to maximize profit while reducing redundancies and costs.
  • Utilize data to understand client behavior as well as business objectives, then help transform those insights into a payment’s strategy and roadmaps
  • Evaluate disputes to research and resolve, based on bank regulations and rules for both US & International transactions
  • Demonstrate a clear understanding of payments, including optimization and reporting, along with dispute processing to help develop and drive strategies for the future
  • Assist in projects to implement new processes which can help with payment processing and minimize risk exposure
  • Independently resolve problems that require in depth investigation and/or research
  • Assist with audits
  • As necessary, performs other related duties


  • Bachelor’s degree in business, finance or accounting or 1-2 years’ experience in a similar role
  • Experience with consumer payments and payment scheme operating regulations (e.g., Visa, Mastercard, etc.) a plus
  • Demonstrated ability to prioritize tasks and meet daily deadlines for projects
  • Strong written and verbal communication skills to inform managers and other stakeholders of results
  • Critical thinking skills with the ability to independently solve problems with data
  • Strong organizational skills, follow up and follow through are required
  • Detail-oriented and data-driven
  • Advanced proficiency using Microsoft Office (Word, Excel, PowerPoint)
  • Ability to learn new subject matters quickly and become a subject matter expert to the lines of business on consumer payment compliance topics


  • Work From Home
  • 100% Employer-paid Medical, Dental and Vision for you and your dependents
  • 401K with employer contribution
  • Unlimited PTO and Parental Leave
  • Stock options

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.

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What are Squire Perks + Benefits

Squire Benefits Overview

* Work From Home (Inside Sales / Remote)
* Strong base salary and commission plan with bonus incentives
* Medical, Dental and Vision fully covered
* 401K with Employer Participation
* Unlimited PTO+

Partners with Nonprofits
Friends outside of work
Daily sync
Open door policy
Highly diverse management team
Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
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Wellness Programs
Mental Health Benefits
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401(K) Matching
Company Equity
Child Care & Parental Leave Benefits
Generous Parental Leave
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Unlimited Vacation Policy
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Casual Dress
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