AI Operations Lead

Pay Ready, Inc.; United States; Remote; USD 90,000 - 140,000; Full time

Job summary

Pay Ready, Inc. is hiring to design and own the decision-making framework for an AI-assisted post-move-out collections system. You will write the standing rules, determine what the agent can and cannot do, and manage escalations to two specialists and agency partners.

You will test theories, measure outcomes, and push for better recovery rates. The role emphasizes ambiguity management, writing clear procedures, and aligning with compliance and property management partners.

Qualifications

• Experience writing clear, actionable policies and standing rules.
• Ability to design processes from undefined situations.
• Comfort with ambiguity and drafting proposals for debate and iteration.
• Experience designing experiments to test hypotheses and learn from results.
• Focus on improving recovery rate over sheer activity.

Responsibilities

• Define the decisions the AI agent cannot make and write rules to govern it.
• Manage how two specialists work the queue and what they escalate.
• Own agency-partner handoffs and ensure the economics of the process.
• Describe and refine what constitutes 'resolved' in each file status.
• Propose and test improvements to increase recovery rate and efficiency.

Job description

We run an AI agent that collects balances residents leave after move-out. It reads the file, decides what to say, writes the message and sends it. No person types to a resident. Someone has to own its edges. Which calls it makes alone. What happens when it reaches a file it cannot finish. Which judgments have to come to a person. When a property ignores a document request for six weeks and the balance sits there, someone decides what we do next. You design that system, then make it collect more without breaking the rules it runs under. You will not be working files yourself. We teach you the business. Post-move-out collections carries its own regulations and nobody arrives knowing them. We are hiring for the ability to turn something undefined into a written process, and for the willingness to work where the answer does not exist yet.

WHAT YOU'LL OWN

• The decisions the agent cannot make. When it reaches a file it cannot finish, it posts a card with a drafted message and a person picks one option: send it, deny it, sweep it to the agency partner, or file a request with the property. You make those calls. More of the work is writing the standing rules that stop the agent having to ask, so the volume of cards falls over time.
• Where the line sits. Four decisions are off-limits to the agent today: payment plan changes, settlement terms, refunds after a revised balance, balance revisions. A second set never reaches a card at all, because outreach stops on the spot: a resident who has died, declared bankruptcy, retained an attorney, or sent a cease and desist. You own both lists and you move the line as the agent earns more room.
• The processes. Most of them are not written down. How a dispute gets worked. What we do when a property goes silent. What 'resolved' means for each file status, defined tightly enough to measure. You will write first versions, find out where they break, and write second versions.
• Two people. Two specialists work the queue day to day. You set what they work, how they work it, and what they escalated.
• The agency partner relationship. Files we cannot resolve sweep to our agency partners. You own whether that handoff works, what shape files come back in, and whether the economics hold. The job includes noticing things like accounts losing payment portal access on the way over, or a file sitting there with nobody assigned to it.
• Recovery rate. You bring a theory about why the number is where it is, run something to test it, and report what you learned, including when it did not work.

WHO YOU'LL WORK WITH

• Two queue specialists: Your team. They work the decision queue day to day.
• Chief Product Officer: Your manager. Expect direct and frequent contact, especially in the first few months.
• Agency partners: Files we cannot resolve sweep to them. You own the relationships and the performance of that handoff.
• Engineering: You file what is broken and what is missing. Much of what you find becomes a change to how the agent behaves.
• Compliance: Signs off on anything that changes what a resident sees or how we treat them.
• Property management companies: The other side of most document requests and disputes

WHAT WE'RE LOOKING FOR

• Property management operations. You have run processes inside a property management company or a multifamily operator. You know what a ledger is, why a move-out statement gets disputed, how a regional manager responds when we ask for a document, and what it takes to get an answer out of a site team. That knowledge is most of the ramp and the slowest part to teach.
• Process building from nothing. You have walked into something undefined, written down how it should work, got people to work that way, and changed it when it turned out wrong.
• Comfort without the answer. Much of this job is deciding something nobody has decided before, writing down why, and moving. The work suits someone whose response to an ambiguous brief is to produce a draft to argue with.
• Experiments. You have had a theory about why a number was bad, designed something to test it, measured, and said plainly when you were wrong.
• Focus on recovery rate over activity. We would rather hear that you tried four things, one worked, and here is the lift, than a report on volume.
• Clear writing. Most of this job lands as written decisions that people and an AI agent follow. Ambiguous writing turns into the agent doing the wrong thing at scale.

Not required

• Collections experience. We teach the applicable regulations and the rest. Deep agency-side habits can work against how we operate.
• Technical background. You file what is broken and shape what gets built. You will not write code.
• AI experience. You need curiosity about working alongside an agent and a willingness to tell it when it is wrong.

First 90 days

• Weeks 1 to 4. Learn the learn the file and understand the applicable legal framework. Work the decision queue yourself alongside the two specialists, enough cards to feel where the agent is weak. Learn how a balance is built, where documents come from, and what the status codes mean. Meet the agency partner.
• Weeks 5 to 8. Take the decisions. You own the standing rules and what the agent does alone. Define the four decision types that have none today: payment plan changes, settlement terms, refunds after a revised balance, balance revisions. Pick one broken process and fix it end to end.
• Weeks 9 to 12. Move the number. Bring a theory about recovery rate, an experiment to test it, and a result. Have a position on whether the sweep to the agency partner is set up the way it should be.

Work Location: 100% Remote. This position is fully remote and can be performed from any location within the United States. You are not required to live near or commute to an office.