Director Technical Program Management Jobs in Massachusetts

Job Description:
Our Team
Chewy's Pet Health team is on a mission to make pet healthcare simpler, more accessible, and a little less stressful for pet parents (and their furry sidekicks). From scaling telehealth to optimizing user experiences across the pet prescription space, we're building products that genuinely make a difference in how people care for their pets.
Engineering is at the heart of that journey. We're a curious, collaborative group that cares just as much about why we're building something as how we build. We celebrate wins, learn from missteps without blame, and continuously raise the bar for ourselves and each other. Whether it's contributing to shared platforms or partnering across teams, you'll find plenty of opportunities to make a real impact and grow along the way
Our Opportunity:
We are looking for a Senior Technical Program Manager - Healthcare B2C at our Boston, MA or Bellevue, WA office. This role will own the portfolio planning, technical coordination, and delivery support for enhancing Chewy's Healthcare B2C platforms like Telemedicine including integrations with checkout, payments, and other partner integrations across our e-commerce and Healthcare teams.
As an Sr TPM, you will operate as a single-threaded owner for large, ambiguous, and business-critical initiatives, influencing strategy and driving execution across multiple teams and organizations.
What You'll Do:
• Own portfolio management for the Healthcare B2C services domain, driving roadmap alignment and execution across multiple teams ensuring transparency at all levels including executive leadership..
• Act as the end-to-end owner for large, cross-functional programs (e.g., telemedicine expansion), 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 strategic 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 execution plans tied to key metrics such as authorization rates, conversion, payment cost, and fraud loss..
• Influence technical architecture and system design 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 cross-team dependencies.
• 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 stakeholders..
• Establish and scale mechanisms (roadmaps, metrics, dashboards, rituals) that improve predictability and execution quality across the Healthcare B2C organization.
What You'll Need:
• Bachelor's degree in computer science 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 with web/mobile technologies (React, TypeScript) and backend systems (e.g., Java, APIs, distributed systems)
• Experience with APM(Datadog, Dynatrace) and AWS technologies ( EC2, SNS, SQS, DynamoDB)
• Proven ability to operate independently in ambiguous problem spaces, defining structure, priorities, and execution plans
• Strong understanding of B2C web applications
• Demonstrated experience influencing technical architecture and business strategy across multiple teams 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
• Preferred: Experience in high scale e-commerce platforms.
The base salary range for this role is $110,500 - $176,000.00.

• 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.
To access Chewy's California CPRA Job Applicant Privacy Policy, please click here.