AI Operations Associate

About Loop

Loop is industrializing services through AI, starting with one of the world's most complex industries: the global supply chain. We're an AI-native company built to solve the systemic data problem that's held logistics back for decades. Our Logistics Data Platform turns fragmented, unstructured data into a trusted foundation that fuels automation, financial clarity, and decision intelligence at scale.


Our momentum is gaining national recognition. Loop was recently named to LinkedIn's 2026 Top Startups list, ranking #1 in Chicago, #4 in San Francisco, and earning a spot on the national list reflecting our growth, innovation, and the exceptional talent and culture driving our success.

Today, Loop serves >20% of the Fortune 100, manages over $30B in supply chain spend, and helps its clients save hundreds of millions of dollars each year.

We recently closed a $95M Series C and are backed by leading investors including Valor Equity Partners, Founders Fund, 8VC, Index Ventures, J.P. Morgan, and more than 50 industry-leading angel investors.

Our team brings deep expertise from Uber, Google, Microsoft, Meta, Amazon, Flexport, C3 AI, VMware, Box, UPS, and C.H. Robinson and we're looking for builders who want to help shape what comes next.

About the Role

The AI Operations team owns the agents and automations that Loop runs for its customers. We build them, test them, measure them, and get them adopted. You'll sit between engineering, product, and operations: finding where manual work lives, building and evaluating the agents that remove it, and proving the impact with numbers. You'll work with internal teams and with operations and finance teams at some of the world's largest brands, so you'll need to explain technical work in plain language.


This is an in-person role based in Chicago/NYC/SF, with the expectation of being in the office 4+ days per week.

What You'll Do

• Build and ship agents. Work with AI engineers to design, configure, and deploy agents that take manual work out of freight audit, contract configuration, cost allocation, and payment workflows.
• Test before you promote. Design and run A/B tests, backtests, and evals on agents, prompts, and rules. Compare variants against a baseline, measure accuracy and regressions, and decide what goes to production.
• Turn operations into numbers. Size problems such as backlogs, exception rates, and overcharges; find root causes; and report impact in dollars, hours saved, touchless rate, and accuracy.
• Run discovery on your own. Shadow internal teams and customer calls, map how work actually gets done, and write clear problem statements that identify the highest-leverage opportunities to automate.
• Own the product lifecycle with product and engineering. Take ideas from discovery through requirements, rollout, adoption, and iteration.
• Drive adoption. Document workflows, write the skills and SOPs that agents and people rely on, and train teammates on new systems.
• Embed with customers. Partner with customer, operations, and product teams at large enterprises to make sure Loop delivers measurable value.

About You

• Agent-building experience. You have built agents or LLM-powered workflows and evaluated them, for example by A/B testing prompts, building eval sets, or comparing model, prompt, or rule variants against a baseline.
• Quantified impact on business processes. You can point to specific referenceable results - which you might even be able to replicate in a mini-case study with us. Please include numbers like these in your application.
• Technical training that carries over to agentic coding tools like Claude Code. You're comfortable in a terminal and with git, and you can read and write Python or TypeScript and SQL. A CS, engineering, or data science background, a bootcamp or certification, or shipped side projects all count. If you do not have this, you will not be considered.
• Product sense. You're familiar with how products are discovered, scoped, launched, and iterated on, and you can run discovery without a playbook.
• Domain experience in at least one of these areas , which reflect the backgrounds of people who have excelled at Loop:

• Freight and transportation: truckload or LTL brokerage, 3PL operations, carrier management, or freight audit and payment
• Parcel and shipping: parcel carrier operations or sales, parcel contract negotiation and optimization, or e-commerce fulfillment
• Merchant inventory and supply chain: warehouse management systems, retail or CPG supply chain, inventory planning, or process improvement (Lean or Six Sigma)
• Credit underwriting and financial analysis: underwriting, credit or risk analysis, investment banking or private equity diligence, or financial data platforms
• Money movement and payments: payments operations, AP/AR, billing and reconciliation, or fintech

• A degree in a quantitative field such as analytics, finance, economics, computer science, or another STEM discipline. Your degree is less important than referenceable impact, entrepreneurial, professional, or otherwise.
• 2+ years of work experience in technology, data analysis, operations, or another technical or quantitative field.
• Eagerness to learn, paired with the ability to execute on hard problems.
• A strong team player who wants to be an early employee at a fast-growing company. We are a Founders Fund funded startup.

Nice to Have

• Experience with LLM APIs, eval frameworks, or prompt management tools
• Experience with rules engines or configuring business logic
• BI and dashboarding experience (Mode, Looker, Tableau, or similar)
• Advanced Excel and data modeling
• Experience building automations, including vibe coding

How to Stand Out

Along with your resume, share one example of an agent, automation, or analysis you built: what problem it solved, how you tested it, and the result in numbers. A link, repo, or short write-up is welcome. You will have a case that tests your agentic ability and you will go over this case in person with an interview panel.

Compensation and Benefits

The base pay range for this role is $80,000 to $125,000 annually. This range reflects the base pay that Loop reasonably expects to pay for the position at the time of hire. Actual compensation will depend on job-related factors, including experience, skills, qualifications, location, and business needs.

In addition to base salary, this role may be eligible for equity. This role is also eligible for Loop's benefits, including health, dental, and vision insurance, 401(k) match, paid time off, paid holidays, free lunch, and parental leave.

Equal Opportunity

Loop is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by law.