Senior Program Manager - Payment Operations - Healthcare

Chewy•Boston, MA

2d•$118,500 - $207,000•Hybrid

About The Position

Chewy is hiring a Senior Program Manager, Payment Operations - Healthcare 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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.