Senior Technical Program Manager

Chewy•Boston, MA

22h•Hybrid

About The Position

Our Opportunity: Chewy is dedicated to being the most trusted and convenient online destination for pet parents (and partners), everywhere. You are a Senior Technical Program Manager – Payments that will lead strategy, planning, and execution across Chewy’s end-to-end payments and gift card ecosystem. Based in Boston, MA or Bellevue, WA, this role will serve as a single-threaded owner for complex, high-impact initiatives spanning checkout, authorization, fraud, settlement, and financial partner integrations across our e-commerce and Healthcare platforms. You will drive alignment across teams, navigate ambiguity, and deliver scalable, reliable payment experiences critical to Chewy’s business.

Requirements

Bachelor’s degree in computer science, Engineering, Business Administration, Finance, or related field and 7+ years of experience (or master’s degree with 5+ years of experience)
5+ years of experience in technical program management, with demonstrated ownership of large-scale, cross-team initiatives
Experience in payments, FinTech, or e-commerce platforms, including payment gateways, processors, tokenization, PCI compliance, and fraud/risk systems
Proven ability to operate independently in ambiguous problem spaces, defining structure, priorities, and execution plans
Strong understanding of end-to-end payment flows (checkout, authorization, capture, refunds, chargebacks, subscriptions)
Demonstrated experience influencing technical architecture and business strategy within several groups without direct authority
Experience driving multi-quarter programs with measurable business impact (e.g., revenue lift, cost reduction, reliability improvements)
Experience with Agile methodologies and delivering complex systems at scale
Familiarity with web/mobile technologies (React, Angular, TypeScript) and backend systems (e.g., Java, APIs, distributed systems)
Experience with CI/CD processes and AWS technologies (CloudWatch, EC2, SNS, SQS)
Experience working with third-party payment providers (e.g. PayPal, Braintree)

Nice To Haves

Experience in high-scale, highly regulated environments (e.g., healthcare, FinTech, PCI)

Responsibilities

Own portfolio management for the Payments domain, driving roadmap alignment and coordination among multiple groups (checkout, payments processing, fraud, finance, analytics), ensuring transparency at all levels including executive leadership.
Act as the end-to-end lead for large, cross-functional programs, such as new payment platform integrations or cost optimization initiatives. Manage these programs from concept through launch and post-launch optimization.
Partner with business and engineering leaders on annual OP1 planning, quarterly business review processes and documentation, and onsite team long-term planning meetings.
Drive planning mechanisms that balance business impact, engineering capacity, and operational risk, making tradeoff decisions in ambiguous environments.
Partner with product, engineering, leaders to define multi-quarter strategy and implementation roadmaps passionate about important measures such as authorization rates, conversion, payment cost, and fraud loss.
Influence system framework and build discussions to ensure scalable, resilient, and secure payment systems, without directly managing engineers.
Define and enforce mechanisms for operational excellence, including SLA/SLO tracking, incident management, and continuous improvement for payment success rates and latency.
Identify, surface, and mitigate risks across programs, including third-party dependencies (processors, gateways), industry requirements (PCI), and financial reconciliation accuracy.
Own executive communication, including bi-weekly Flash updates, providing clear, concise updates on program health, risks, tradeoffs, and business impact, and driving alignment across senior Team Members.
Establish and scale mechanisms (roadmaps, metrics, dashboards, rituals) that improve predictability and execution quality across the payment’s organization.
Mentor junior TPMs and influence teams to adopt strong program management and agile standard methodologies, raising the overall bar for execution.
Lead cross-team coordination during high-severity incidents (e.g., payment outages, elevated failure rates, fraud spikes), driving resolution and postmortem improvements.

Benefits

401k
new hire and annual equity grant
annual bonus
medical/Rx insurance
vision insurance
dental insurance
life insurance
disability insurance
hospital indemnity insurance
critical illness insurance
accident insurance
parental leave
family services benefits
backup dependent care
flexible spending accounts
telemedicine
pet adoption reimbursement
employee assistance program
10% off pet insurance
20% off at Chewy.com
unlimited PTO (subject to manager approval)
six paid holidays per year
paid sick and family leave (in compliance with applicable state and local regulations)