Director, AI, Agents & Data Intelligence

About the role

Trolley, a fast-growing remote creative operations company, is hiring a Director, AI, Agents & Data Intelligence. You will own AI agents and data intelligence across the business, build the first systems yourself and lead a small data team within a new team. The role is full-time and remote, with a 6-hour overlap with Pacific Time required, and pays $6,000 to $7,500 USD per month.

Key responsibilities

• In the first 90 days, set up the insights system, get it used daily and ship the first three prioritized agents.
• Build custom agents on company data using LLMs (Claude, ChatGPT, Gemini), MCP integrations and AI-native tools, with tasks routed to the best-fit model.
• Run finance agents for payouts, settlements, gift cards, 3PL reconciliations, commissions, bonuses and NetSuite journal entries, with more than half of month-end close automated.
• Run operations agents for item creation, PO tracking, inventory checks and wholesale order exceptions.
• Set up a daily morning sweep, approval rules, access controls, audit trails and monthly cost and accuracy reports.
• Provide a single view of sales channels and a single customer view across websites, stores and VIP associates, with metrics such as CAC, LTV, ROAS and sell-through.
• Partner with the Director, Commerce & Enterprise Technology and work with the Co-CEOs, Finance, Operations, Marketing and Client Experience.

Required profile

• Has shipped AI agents or data products used by a whole company and led data science, analytics engineering, machine learning or software engineering teams.
• Built hands-on: strong SQL and Python, LLMs and agents including MCP, retrieval and evaluation, cloud data warehouses such as BigQuery or Snowflake, APIs, data pipelines, Shopify, NetSuite and Amazon data, and A/B testing.
• Business-first, cost-conscious, able to explain models and risk in plain language to non-technical leaders.
• Nice to have: experience at a physical consumer goods brand with DTC, retail and wholesale channels, and a background in a quantitative field.

Hiring includes a 15-minute interview, a skills test, a 30-minute interview with the manager and a final interview with the CEO. Applications are made through the link provided in the original posting.