Terminal Manager Jobs in Boston, MA (NOW HIRING)

Chewy's mission is to be the most trusted and convenient destination for pet parents and partners everywhere. We view pets and pet parents as family and are obsessed with meeting their needs and exceeding expectations through every interaction. Within Chewy, the Payments team improves the customer and care team experience by launching better ways to pay, increasing payment success, strengthening reliability, and reducing the cost and friction of payments.

Chewy is hiring a Senior Program Manager, Payment Operations - Healthcare in Bellevue, WA, Plantation, FL, or Boston, MA to lead payment health, readiness, and optimization across Chewy Healthcare. In this role, you will be the senior operational owner for in-clinic, digital, and recurring payments used by customers and clinic care teams, and internal operators. You will manage performance, partner escalations, and cross-functional execution for capabilities that are critical to customer experience and business outcomes.

The ideal candidate is an experienced payments and operations leader who has owned outcomes in a scaled retail, fintech, ecommerce, marketplace, subscription, or omnichannel environment. This person combines payments depth with senior program leadership and can move between strategic planning and hands-on issue resolution. They have improved one-time and recurring payment experiences, including authorization performance, stored credentials, tokenization, retry strategies, and decline recovery. They can quickly build credibility, simplify complex topics, identify customer and business impact, and lead partners across Product, Engineering, Clinic Operations, Customer Care, Analytics, Finance, Accounting, Legal/Compliance, and external payment providers.

What You'll Do

• Own the operational roadmap for Healthcare payments across in-clinic, digital, and recurring workflows.
• Define, monitor, and improve payment metrics such as success rate, authorization performance, recurring payment recovery, terminal reliability, refund/void quality, decline trends, incident volume, and SLAs.
• Strengthen recurring payment operations, including stored credential health, tokenization, card lifecycle events, payment retries, decline recovery, account updater processes, and payment method reliability.
• Lead Healthcare payment launches, enhancements, defect resolution, and operational readiness across Product, Engineering, Clinic Operations, Customer Care, Analytics, Finance, Accounting, Legal/Compliance, and external partners.
• Identify payment defects and reliability risks, quantify customer and financial impact, and drive prioritized resolution.
• Build and improve operating mechanisms such as dashboards, runbooks, escalation paths, incident response processes, post-incident reviews, partner reviews, and readiness checklists.
• Manage external payment providers, terminal providers, gateways, processors, and other third parties against SLAs, roadmap dependencies, issue resolution, and improvement plans.
• Lead incident response and root-cause analysis in partnership with internal and external teams; convert learnings into durable prevention and monitoring mechanisms.
• Develop executive-ready narratives, business reviews, and recommendations that connect payment performance with customer experience, care team experience, cost, risk, and business impact.
• Serve as a payments subject matter expert for card-present, card-not-present, recurring payments, terminal, refund, reconciliation, and operational support workflows across Healthcare.

What You'll Need

• Bachelor's degree in business, finance, operations, technology, or related field, or equivalent practical experience.
• 8+ years of experience in payments, payment operations, fintech, ecommerce, retail, healthcare operations, marketplace operations, subscription/recurring payments, or another scaled operational environment.
• 5+ years leading complex cross-functional programs with Product, Engineering, Analytics, Finance, Accounting, Customer Care/Operations, Legal/Compliance, and external partners.
• Track record owning payment KPIs and operational outcomes such as payment success rate, authorization rate, decline rate, terminal availability, refund/void performance, dispute rate, reconciliation quality, cost of payments, or SLA performance.
• Direct experience with card-present and card-not-present payment flows, including gateways, processors, acquirers, issuers, card networks, digital wallets, payment terminals, stored credentials, tokenization, settlement, refunds, disputes, and reconciliation.
• Experience with recurring or subscription-like payment programs, including stored credentials, payment retries, decline recovery, account updater/card lifecycle management, payment method lifecycle events, or recurring billing reliability.
• Experience supporting omnichannel, healthcare, clinic, field, retail, marketplace, ecommerce, or service-oriented environments where both customer and operator workflows matter.
• Strong analytical capability with the ability to use payment data, processor reporting, decline trends, defects, and customer/care team feedback to identify root causes and drive action.
• Proven ability to operate in ambiguity, dive into details, and lead issue resolution without direct authority.
• Strong vendor and partner management experience, including performance reviews, escalations, SLA management, roadmap alignment, and operational improvement plans.
• Excellent written and verbal communication skills, including experience preparing executive-level narratives, business reviews, and decision recommendations.
• Ability to deliver time-sensitive initiatives while maintaining strong attention to detail and follow-through.
• Ability to travel up to 15% of the time.

Preferred Qualifications

• Experience with payment terminals, order management, point-of-sale systems, ecommerce, or healthcare/clinic payment workflows.
• Experience launching or scaling payment capabilities across physical locations, field operations, or distributed teams.
• Experience improving payment observability, incident response, support models, or partner performance in a high-volume environment.
• Experience with digital wallets, debit routing, account updater/card lifecycle management, or payment optimization strategies.

Success in This Role Looks Like

• Healthcare payment workflows are reliable, measurable, and supported by clear operating mechanisms across in-clinic, digital, and recurring experiences.
• Customer, clinic, and care team friction is identified quickly, quantified clearly, and resolved through strong cross-functional ownership.
• Payment partners are managed through business reviews, escalations, SLAs, and improvement plans.
• Payment incidents have clear response paths, root-cause ownership, durable prevention actions, and improved monitoring.
• Senior leaders have a clear view of payment performance, risks, tradeoffs, and investment needs across Chewy Healthcare.

• The specific salary offered to a candidate may be influenced by a variety of factors including but not limited to the candidate’s relevant experience, education, and work location. In addition, this position is eligible for 401k and a new hire and annual equity grant. C08+ positions may also be eligible for annual bonus.

We offer different types of insurance and benefits, such as medical/Rx, vision, dental, life, disability, hospital indemnity, critical illness, and accident. We offer parental leave, family services benefits, backup dependent care, flexible spending accounts, telemedicine, pet adoption reimbursement, employee assistance program, and many discounts including 10% off pet insurance and 20% off at Chewy.com. 

Exempt salary team members have unlimited PTO, subject to manager approval. Team members will receive six paid holidays per year. Team members may be eligible for paid sick and family leave in compliance with applicable state and local regulations. 

Chewy is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, ancestry, national origin, gender, citizenship, marital status, religion, age, disability, gender identity, results of genetic testing, veteran status, as well as any other legally-protected characteristic. If you have a disability under the Americans with Disabilities Act or similar law, and you need an accommodation during the application process or to perform these job requirements, or if you need a religious accommodation, please contact CAAR@chewy.com.

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