Insurance Program Manager Jobs in Andover, MA (NOW HIRING)

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 

Chewy is seeking a Technical Program Manager (TPM), Pet Health Engineering to lead high-impact, cross-functional programs across our Pet Health ecosystem. This role can be based in Boston, MA or Seattle, WA. 

You will own delivery across critical customer journeys and foundational platforms, including Telemedicine, prescription/Rx workflows, and Pet Insurance. These programs sit at the intersection of customer experience, healthcare workflows, and scalable platform architecture. 

In this role, you will partner closely with Engineering, Product, Data, and Platform teams to deliver complex, multi-quarter initiatives that directly impact customer experience, operational efficiency, and business growth. 

As a TPM, you will operate at the intersection of technology, product, and execution. You’ll own end-to-end delivery across distributed systems and influence how we scale Pet Health at Chewy. 

What You’ll Do 

• Own and drive end-to-end delivery of complex technical programs across Chewy’s Pet Health technology stack, from concept through launch and post-launch optimization 

• Work with engineers to clarify technical requirements and then turn those into milestones and execution plans 

• Navigate complex system dependencies across customer-facing applications, backend services, and platform infrastructure 

• Identify risks, tradeoffs, and bottlenecks early; drive mitigation strategies and escalate effectively when needed 

• Navigate ambiguity to formulate a plan and drive alignment across teams to achieve that plan 

• Utilize planning mechanisms that balance business impact, engineering capacity, and operational risk 

• Partner with engineering teams in architecture and design discussions to understand system tradeoffs and inform execution plans  

• Establish and drive operational rigor through program reviews, metrics, status reporting, and retrospectives  

• Drive clear communication and alignment across technical and non-technical stakeholders, including leadership 

What You’ll Need 

• 5+ years of experience as a Technical Program Manager, Program Manager, or similar role delivering large-scale, cross-functional technical initiatives. 

• Proven experience leading multi-team, multi-system programs in a fast-paced, high-growth environment  

• Strong technical fluency with distributed systems, APIs, data pipelines, and cloud-based architectures  

• Ability to engage in architecture discussions, understand system tradeoffs, and influence technical decision-making  

• Experience managing complex dependencies across engineering, product, data, and business stakeholders  

• Strong communication skills, with the ability to synthesize complex technical concepts into clear, actionable insights for diverse audiences, including executives  

• Highly organized, execution-focused mindset with a strong sense of ownership and bias toward action 

Nice to Have 

• Experience building or scaling customer-facing products in eCommerce or marketplace environments  

• Experience in healthcare, pharmacy, or other regulated domains  

• Experience working on systems that span both customer-facing experiences and internal platforms