Senior Digital Commerce Strategist & Architect

Caterpillar Inc.•Chicago, IL

1d•$128,470 - $208,770•Onsite

About The Position

This is a senior level role that blends strategy with hands-on execution: you'll help define what we build in commerce today and structure it so it can power AI-driven experiences tomorrow. You'll work across product, engineering, marketing, and data to improve store entry and way-finding, elevate the equipment experience, and strengthen the underlying data model and taxonomy that everything else depends on. You'll also support current AI execution bringing enough fluency with models, prompting, and retrieval to be a real partner on that side of the work, even though it isn't the center of gravity for the role. The right person is part systems thinker, part builder. You should be comfortable mapping a customer journey on a whiteboard in the morning, sketching a taxonomy or data contract by lunch, and reviewing a prompt or experiment design in the afternoon. You think in terms of how things connect, pages, data, content, models and you can hold the whole picture without losing the details.

Requirements

Decision Making and Critical Thinking: Knowledge of the decision-making process and associated tools and techniques; ability to accurately analyze situations and reach productive decisions based on informed judgment.
Effective Communications: Understanding of effective communication concepts, tools and techniques; ability to effectively transmit, receive, and accurately interpret ideas, information, and needs through the application of appropriate communication behaviors.
Software Change Request Management: Knowledge of software change request management; ability to manage software change requests from customers, prospective customers, vendors, and internal staff.
Software Engineering: Knowledge of software engineering; ability to deliver new or enhanced fee-based software products.
Software Problem Management: Knowledge of strategies, practices and tools for resolving software problems; ability to manage software problems in installed software products.
Software Product Business Knowledge: Knowledge of and experience with the business aspects and operation of a software product; ability to manage install base, current uses, future plans, and product vision.

Nice To Haves

5-7+ years of experience in digital commerce, e-commerce strategy, or a closely related field, with demonstrated hands-on execution.
Experience working on commerce surfaces such as store entry, navigation/wayfinding, PDPs, search, or merchandising ideally with direct exposure to product information architecture and taxonomy.
Working understanding of commerce data: product data models, content structures, attribution, and how analytics flows through the stack.
Working knowledge of core AI/ML concepts (LLMs, embeddings, retrieval, recommendation systems) and hands-on experience using prompting techniques and RAG patterns in a real work context.
Familiarity with AI orchestration frameworks (LangChain, LlamaIndex, or similar) at a conceptual level.
Comfort evaluating tradeoffs across AI approaches (prompting vs. retrieval vs. fine-tuning) at a directional level, and translating those tradeoffs into business language.
Strong project management skills and the ability to run multiple initiatives in parallel.
Experience with taxonomy, PIM, or structured content systems.
Strong data and analytics skills: GA4, Tableau, Looker, or similar BI tools, plus working SQL.
Experience with A/B testing methodologies and experimentation frameworks.
Familiarity with semantic search, vector databases (Pinecone, Weaviate, Chroma), or AI-assisted discovery.
Exposure to UX or service design thinking, comfort collaborating closely with designers and researchers, and a feel for how IA, content, and interaction patterns shape the customer experience.

Responsibilities

Partner with product to shape store entry and wayfinding how customers land, orient, and navigate toward the right equipment for them.
Design and continuously improve the equipment experience: how products are presented, compared, configured, and contextualized across the journey.
Own the underlying commerce data model and taxonomy product attributes, content structures, navigation logic, and the relationships between them with an eye toward downstream usability for both humans and AI systems.
Translate business goals, customer research, and behavioral data into clear strategic recommendations and roadmaps for the product team.
Define KPIs and measurement frameworks for commerce initiatives; design and run A/B tests to validate impact on conversion, AOV, and customer lifetime value.
Build business cases and ROI models for proposed initiatives and present findings to senior leadership.
Collaborate with engineering to define API contracts, content models, and integration patterns that scale.
Support current AI execution across commerce helping evaluate opportunities, scope initiatives, and translate them into something the team can ship.
Help structure commerce data, content, and taxonomy so it's AI-ready: clean, well-labeled, retrievable, and semantically meaningful.
Contribute to feasibility assessments for AI initiatives, including model selection considerations, data requirements, and integration approach.
Help define guardrails, evaluation criteria, and QA processes for AI-driven features before they reach customers.
Stay current with the AI landscape at a working level enough to be a credible thought partner and to spot where AI genuinely helps versus where it doesn't.