Wayfair is hiring a Senior Manager, Technical Program Management to own the full lifecycle of massive, complex, cross-functional programs. The role requires anticipating and de-risking bottlenecks, managing escalations, making smart, data-informed trade-off decisions, and balancing customer and business needs within real technical constraints.
This isn't a status-reporting role. The TPM is explicitly accountable for preventing the traditional failure modes that sink large programs: a poor understanding of the customer or business problem, weak cross-team collaboration, interdependencies that never get mapped, weak technical solutioning, gaps in testing, or success criteria that were never clearly defined in the first place.
The role sits at the intersection of Engineering and Product leadership, leading cross-functional delivery of large-scale replatforming programs — defining program structure, and aligning goals, milestones, and delivery schedules across engineering, product, analytics, and design.
What You’ll Do
- Manage the full lifecycle of a massive, complex, cross-functional program end to end.
- Anticipate and de-risk bottlenecks before they threaten a delivery date.
- Manage escalations and make smart, data-informed trade-off decisions under real technical and business constraints.
- Balance customer needs and business needs within technical constraints, rather than treating them as automatically aligned.
- Own the prevention of the traditional program failure modes: bad understanding of the customer/business problem, weak collaboration, interdependencies not being mapped, weak technical solutioning, gaps in testing, and unclear success measurement.
- Communicate and align with senior leadership across both the Engineering and Product organizations — effectively painting with context to drive high-quality decisions.
- Lead cross-functional delivery of large-scale replatforming programs: define program structure, and align goals, milestones, and delivery schedules across engineering, product, analytics, and design.
What You’ll Need
- 5+ years of experience in software engineering, software product management, software development management, or technical program management.
- A BS in computer science or a related technical discipline, or an MBA with a focus on tech and engineering management, plus a track record of delivering complicated software solutions in a scaled agile environment.
- Executive-level communication skills, including the ability to distill complex technical trade-offs into clear, data-driven narratives.
- Deep experience applying Agile and Lean methodologies at scale, across multiple teams and workstreams.
Role Context (from related Wayfair TPM postings)
- Wayfair's Technical Program Management org runs large-scale replatforming and modernization programs on core, customer-facing shopping surfaces — the kind of work where a program spans engineering, product, analytics, and design simultaneously rather than sequentially.
- Comparable senior TPM postings on the same team call out deep familiarity with modern software architecture (microservices, APIs) and the ability to operate credibly alongside engineers working in stacks like React, Java, GraphQL, and Kafka — not to write the code, but to make informed trade-off calls about it.
- Note: Wayfair's own career site returned a 429 to automated fetches while preparing this file, so the sections above are reconstructed from the publicly indexed text of this listing (job ID 2-13501) plus closely related, currently-cached Wayfair TPM postings on the same team. Verify current comp, location/work-mode, and any updated requirements directly on wayfair.com before the interview.
Question
Tell me about yourself.
Opening Statement (~45–90 sec)
Thank you for making time today. I'm an Enterprise Technology Executive with 18+ years of experience defining Technical Program Strategy, governing complex portfolios, and orchestrating large-scale, cross-platform execution. I'd frame my background across six things: • Strategic Technical Delivery — I define and lead Technical Program Strategy for enterprise cloud infrastructure and AI initiatives, including executive vision and governance for a Kubernetes-based Internal Developer Platform spanning 300+ production clusters and 1,300+ engineering teams. • Cross-Platform Execution — I orchestrate execution across Engineering, Product, Design, Data Science, and Infrastructure — from a 2,100+ application migration to a resilient AWS multi-account architecture, to the Prime Video and Freevee platforms serving 120M+ users. • Architecture & Operational Excellence — I partner with technical leaders on scalable, resilient architecture and delivery governance, which drove a 70% increase in developer productivity and cut deployment lead time from 2 weeks to under 45 minutes. • Executive Advisory & Influence — I serve as a trusted advisor to senior leaders today, translating technical trade-offs into business implications and guiding prioritization amid competing demands. • Elevating the TPM Discipline — I founded and scaled a centralized TPM Center of Excellence, mentoring TPMs and delivery leads to bring consistency and rigor to ambiguous environments. • AI-Native Practice — I hold Anthropic's Claude and MCP certifications alongside AWS's AI Practitioner and Generative AI Developer credentials, and I lead Technical Program Strategy for AI initiatives directly in my current role. What I'd bring to Wayfair is that same six-part operating model, applied to Wayfair's replatforming programs from day one.
Detailed Response
Own Strategic Technical Delivery
In my current Director, Technical Program Management role, I define and lead the Technical Program Strategy for enterprise cloud infrastructure and AI initiatives — including the executive vision, operating model, and governance for a unified Kubernetes-based Internal Developer Platform spanning 300+ production clusters and 1,300+ engineering teams, built to improve developer experience and accelerate microservices delivery. I establish and track measurable delivery metrics, success criteria, and executive-level reporting on every program I run — deployment lead time cut from 2 weeks to under 45 minutes, and $3.5M in annualized AWS savings captured alongside 99.9% operational resilience on the cost-governance program.
Lead Cross-Platform Execution
In my current role, I partnered with engineering and product leaders to orchestrate the migration of 2,100+ applications to a resilient AWS multi-account architecture, reducing systemic blast-radius risk while maintaining 99.99% availability. That same cross-platform discipline is what I ran at Amazon: orchestrating the Prime Video and Freevee ad-supported platforms for 120M+ users meant coordinating execution across Engineering, Product, Design, Data Science, and Infrastructure simultaneously — integrating low-latency OTT infrastructure, high-concurrency APIs, microservices, and distributed data models across web, mobile, and streaming ecosystems. I anticipated and mitigated delivery risk across those platforms in a genuinely high-ambiguity environment, adjusting scope and timelines dynamically to protect the business metrics that mattered — which is what let inventory yield improve 70% and creative redundancy drop from 40% to 2% without sacrificing 99.99% availability.
Influence Architecture and Operational Excellence
I partner directly with engineering and product leaders to shape scalable, resilient architecture and delivery governance. The Kubernetes-based Internal Developer Platform I helped architect across 300+ production clusters embeds governance directly into the pathway every one of 1,300+ engineering teams uses — automated provisioning, standardized delivery pathways, and embedded security controls — which unlocked a step-change in execution efficiency: 70% higher developer productivity and deployment velocity, with deployment lead time cut from 2 weeks to under 45 minutes. I drove that same governance discipline into cloud cost-optimization and AIOps across a 2,000+ server compute-instance footprint, securing $3.5M in annualized AWS savings while maintaining 99.9% operational resilience and strengthening executive insight into operational efficiency.
Advise and Influence at the Executive Level
I serve as a trusted advisor to senior leaders today, translating technical trade-offs into clear business implications and guiding prioritization decisions amid competing platform, product, and business demands — a standing part of my role, not something I invoke only when a program is at risk. I bring the same lens to emerging technology: I track AI, cloud, and platform-engineering trends directly through hands-on certification, so the long-term technical direction I advise leadership on reflects where the industry is actually heading, not just where it's been.
Elevate the TPM Discipline
I founded and scaled a centralized TPM Center of Excellence specifically to drive consistency, rigor, and clarity into ambiguous or evolving organizational environments — the same discipline that let 11 cross-functional organizations report program health on one shared structure instead of eleven inconsistent ones. Mentoring TPMs and cross-functional delivery leads through that CoE is how the discipline scales beyond any single program I'm personally running.
AI Experience and Accomplishments
I hold Claude 101, Claude Code 101, AI Fluency Frameworks, Claude with Amazon Bedrock, and MCP Advanced Topics certifications from Anthropic, alongside AWS Certified AI Practitioner and AWS Certified Generative AI Developer — and I lead Technical Program Strategy for enterprise cloud infrastructure and AI initiatives directly in my current role. Concretely, that means applying AIOps and model-assisted anomaly detection across a 2,000+ server compute-instance footprint to catch cost and reliability drift early, which is part of what secured $3.5M in annualized AWS savings while maintaining 99.9% operational resilience — plus working hands-on with generative AI, LLMs, RAG pipelines, and MCP-based tooling as part of the broader AI/ML strategy I own.
Closing Statement
What draws me to this role is that it isn't asking me to learn a new discipline — it's asking me to bring that same six-part operating model, strategy through AI-native practice, to Wayfair's replatforming programs.