AI Enablement & Systems Manager

Reports To: Senior Director of E-Commerce, DTC Brands

Location: Milwaukee, WI (Hybrid) 

Employment Type: Full-Time, Salaried, Exempt 

About Wantable  

At Wantable, we’re redefining retail through personalization. Our membership-based model and proprietary technology empower us to curate products that help customers discover confidence and joy through style. 

We are building an AI-first company. Teams across Marketing, Merchandising, Finance, Operations, CX, and Engineering are actively deploying AI agents and workflow automations to automate processes, generate insights, and amplify decision-making across the business.

We’re hiring a Manager-level leader to own and scale the infrastructure that powers AI across the entire organization.

About the Role

The AI Enablement & Systems Manager owns the architecture, governance, performance, and cost structure of Wantable’s internal AI ecosystem and sits at the intersection of LLM's, agents, workflow automation, and internal AI infrastructure.

This is a systems-first role focused on building stable, scalable infrastructure for AI agents and automations across the company. While you will support departments and drive adoption, your primary responsibility is to design and maintain the underlying frameworks, integrations, guardrails, and standards that make AI reliable and production-ready.

You will:

• Architect and maintain our AI automation ecosystem
• Standardize infrastructure and workflows
• Own AI tool and API budget management
• Ensure cost efficiency, security, and reliability
• Establish governance and best practices
• Serve as the internal authority on AI systems for the entire organization

If you're energized by connecting systems, debugging API integrations at 2am because you want to figure it out, and teaching non-technical people to work with AI,  this role is for you.

What You’ll Do

Own AI Infrastructure & Architecture

• Design and maintain Wantable’s AI systems architecture
• Deploy and manage AI agents across departments
• Architect agent hierarchies (master agents, sub-agents, permissions, access controls)
• Build scalable workflow automations that integrate AI with business systems
• Implement retrieval-based workflows (RAG), tool-calling, and multi-step agent orchestration
• Ensure systems are production-ready, stable, secure, and documented

Integrations & Internal Tooling

• Build and maintain integrations with:
• Asana
• Google Workspace
• Zendesk
• Ecommerce & operations platforms
• Internal systems (e.g., Modus)
• Develop lightweight internal tools (dashboards, bots, web apps)
• Standardize API usage, authentication methods, and webhook handling
• Maintain secure data handling practices across AI workflows

Own the AI Tool Budget & Cost Governance

• Manage and optimize AI API usage across LLM providers
• Monitor departmental usage via API keys or cost centers
• Optimize model selection for cost vs. performance
• Forecast AI spend and maintain predictable budgets
• Recommend tool stack changes based on ROI and reliability
• Own vendor evaluations and purchasing decisions

Standardization, Governance & Knowledge Management

• Establish standards for:
• Agent configuration
• Naming conventions
• Documentation
• Prompt versioning
• Own the shared repository for:
• Company knowledge
• SOPs
• Prompt libraries
• Agent configurations
• Implement guardrails for safe and responsible AI usage
• Maintain version control and regression testing processes
• Create reusable templates for departmental AI deployments

Support & Enablement

• Serve as the internal escalation point for AI agent issues
• Debug integration failures, workflow instability, and memory issues
• Train department leads on agent usage and best practices
• Create onboarding documentation and internal playbooks
• Build a network of AI champions across departments

Requirements

What We’re Looking For

• Hands-on experience with workflow automation tools (e.g., N8N, Make, Zapier, or similar)
• Strong understanding of modern LLM ecosystems (Claude, OpenAI, Gemini, etc.)
• Experience building production-grade AI agents and automations
• Experience with RAG, tool-calling, and multi-step orchestration
• API integration expertise (REST, webhooks, JSON)
• Scripting ability (Python and/or JavaScript/Node.js)
• Git/GitHub proficiency
• Strong understanding of model tradeoffs (latency, cost, safety

Nice To Have

• Experience with AI agent frameworks or orchestration platforms
• Prompt engineering and evaluation frameworks
• E-commerce, retail, or DTC experience
• Cloud or self-hosted infrastructure experience
• SQL and data warehousing familiarity
• Experience building internal AI governance programs

How We Work at Wantable

• High ownership. You are trusted to make decisions that directly impact customers and financial performance.
• Hard-working and hands-on. We move fast, stay scrappy, and focus on impact.
• Independent thinkers. We value leaders who confidently make data-driven decisions without layers of approvals.
• Low bureaucracy. We avoid committees, long processes, and unnecessary steps.
• Love of fashion & product. We combine data with intuition to create experiences customers love.
• Results over pedigree. What you’ve built matters more than where you’ve been.

Role-Specific Outcomes

First 2 Weeks

• Document current AI ecosystem and infrastructure
• Identify architectural gaps and cost risks
• Deploy at least one structured automation
• Establish visibility into AI spend

First 30 Days

• Standardize agent deployment templates
• Implement cost monitoring dashboard
• Deploy at least two new production-ready departmental AI automations
• Reduce ad-hoc AI usage by centralizing infrastructure
• Resolve 90% of support issues within 24 hours

First 60 Days

• Every major department runs on stable, governed AI automations
• AI costs are predictable and optimized
• Deployment time for new automations is reduced to days
• Infrastructure is documented, scalable, and secure
• Wantable has a mature internal AI operating system

Benefits

Why Wantable?

• Be part of a dynamic, fast-growing company that has innovation and creativity embedded in its DNA.
• A chance to shape our customers’ journey and leave a lasting impact on their self-confidence, one order at a time.
• Join a collaborative environment where your ideas matter, your efforts are rewarded and you can see results in real time.

We have a laid-back, casual environment in a state-of-the-art HQ in Walkers Point.

We offer flexible schedules, paid parental leave (mothers AND fathers), and a private room for nursing mothers.

Even more exciting: paid vacation and seven paid holidays per year, plus a 50% discount on all merchandise. You’ll be eligible for the discount on your first day.

Important, but maybe less thrilling: we have ample parking, we offer medical (traditional and high deductible), dental, and vision insurance, as well as a 401K (both pre-tax and Roth options).