The all-in-one platform to power your Barbershop Operations
The Role
Lead strategy for SQUIRE's embedded payments platform, managing merchant and customer experiences while ensuring compliance and scalability.
Summary Generated by Built In
WHO WE ARE
SQUIRE is the leading business management system designed for the needs of barbers, shop owners, and their communities. We believe the pursuit of artistry and autonomy should not be restricted by the complexities of running a business. With SQUIRE, we provide custom-branded tools, resources, and guidance to help barbers of all stages and experience levels attract and retain more customers, efficiently manage their shop operations, and increase their revenue.
Founded in 2015, SQUIRE is trusted by more than 30,000 barbers across 5,000+ shops in more than a thousand cities worldwide. From streamlined booking and opening new shops to real-time earning dashboards and building lasting customer relationships, SQUIRE supports shop owners in seamlessly bridging the gap between their personal craft and business goals. SQUIRE enables barbers everywhere to unlock their full potential both as artists and as entrepreneurs.
For more information, please visit getsquire.com or download the SQUIRE app from the App or Play Store.
SUMMARY
We are looking for a Principal Product Manager, Payments to lead the strategy and execution of our embedded payments platform within a B2B2C vertical SaaS ecosystem. Our platform enables businesses to seamlessly accept, manage, and reconcile payments from their end customers, processing $1B+ in annual transaction volume.
This role owns the full payments experience across our software, balancing merchant needs, end-customer experience, compliance, and platform scalability. You’ll work across product, engineering, risk, compliance, and go-to-market teams to ensure payments are a growth engine—not just infrastructure.
JOB DUTIES AND RESPONSIBILITIES
- Product Strategy & Platform Ownership
- Define and own the payments product vision and multi-year roadmap for a B2B2C vertical SaaS platform.
- Lead strategy across embedded payments, onboarding, pricing, settlement, payouts, refunds, disputes, and reconciliation.
- Ensure payments are tightly integrated into core SaaS workflows, driving merchant adoption, retention, and ARPU.
- Evaluate and launch new capabilities such as industry-specific payment flows, financing, subscriptions, and value-added services.
- Merchant & End-Customer Experience
- Deeply understand the needs of platform customers (businesses) and their end users (consumers).
- Design intuitive experiences for merchant onboarding, configuration, reporting, and cash flow visibility.
- Optimize checkout and payment flows to maximize conversion, authorization rates, and customer satisfaction.
- Execution & Cross-Functional Leadership
- Partner with engineering to deliver highly reliable, scalable payment systems that support peak volumes and growth.
- Translate complex platform requirements into clear PRDs, APIs, and success metrics.
- Coordinate across risk, compliance, finance, operations, sales, and customer success to deliver end-to-end solutions.
- Lead launches, migrations, and platform upgrades with minimal disruption to merchants.
- Risk, Compliance & Trust
- Own the product partnership with Risk, Compliance, and Legal to meet requirements including PCI, AML, KYC/KYB, and card network rules.
- Balance friction and fraud prevention across merchant onboarding and end-customer payment flows.
- Drive proactive improvements to disputes, chargebacks, and fraud tooling and processes.
- Growth, Data & Outcomes
- Define and track KPIs including payment adoption, take rate, authorization rate, payment success rate, fraud loss, and settlement SLAs.
- Use data, experimentation, and customer insights to prioritize roadmap decisions.
- Partner with finance and GTM teams on pricing, monetization, and payments-led growth strategies.
- Leadership & Influence
- Serve as the payments domain expert within the product organization.
- Mentor PMs and raise the bar for platform thinking and execution.
- Influence senior leaders with clear narratives around tradeoffs, risk, and opportunity.
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 AND QUALIFICATIONS
- 8+ years of product management experience, including significant ownership of embedded or platform payments.
- Proven experience building products in a B2B2C, marketplace, or vertical SaaS environment.
- Hands-on experience with merchant onboarding, settlement, and reconciliation at scale.
- Strong understanding of the payments ecosystem (processors, networks, acquiring, issuing).
- Comfort operating in regulated environments and partnering closely with compliance and risk teams.
- Ability to balance long-term platform investments with near-term revenue and customer needs.
- Experience monetizing payments within vertical software.
- Familiarity with small business payment workflows
- Experience expanding payments into new verticals or geographies.
Nice to Have
WHAT WE OFFER
- Base Salary ($200,000 - $220,000)
- New hire stock grant
- 100% employer paid medical, dental, and vision insurance for you and your dependents
- 401K plan with company contribution
- Generous PTO and Parental Leave 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 [email protected] and someone on our team will respond to your request.
EEO Provision
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.
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.
E-Verify Participation
SQUIRE participates in E-Verify. Learn more about E-verify here.
Top Skills
APIs
Payments
SaaS
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The Company
What We Do
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 is the market leader in technology solutions for the barbershop industry.
SQUIRE is a Series D company and has raised over $165M to date.
For more information, please visit getSquire.com or download the SQUIRE app from the App or Play Store.
Why Work With Us
We're not just another start-up; we're a community of innovators, drivers, and achievers driven by our mission - to elevate, celebrate and empower the barbering community.
Check out our Culture Book to learn more - https://handbooks.getsquire.com/recruiting.
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