Senior AI/ML Lead

About RentFlow 

RentFlow is tackling a hair-on-fire problem for small and medium businesses across the U.S.: the way their rent is paid each month is fundamentally misaligned with how cash actually comes in. 
We’re building the infrastructure layer to fix that. 
Today, ~50% of U.S. businesses are late on rent in any given month. The rest face invisible struggles to pay on time, undermining their stability month after month. 
The core issue is structural: rent hits as a single fixed lump sum on the 1st, stacked on top of every other major monthly bill, while revenue and other expenses flow in unevenly. This forces healthy businesses into recurring cash-flow stress and is a major driver of business closures. 
RentFlow is the first startup to turn fixed business rent into a cash-flow-synced product, underwritten in real time from transaction-level data to prevent issues before they even surface. 
This opens up a $20B+ rent-splitting market and creates a natural wedge into an AI CFO layer for businesses and data opportunities we're uniquely positioned to own. 
We’re seed-stage, live since May 2025, and growing quickly. We’re ramping up partnerships with the leading rent payment platforms in the U.S., fast-growing SMB software companies, and major property players. 

Early-Stage Opportunity 

We’re hiring our Senior AI/ML Lead to own underwriting, risk intelligence, LLM applications, and financial data insights end-to-end.
This is a foundational role. You’ll build systems that make real financial decisions in production, while also turning the data generated through RentFlow into entirely new products for tenants and landlords. 
You’ll work directly with the founders and have full ownership over both technical direction and business outcomes. 

What You’ll Do 

• AI applications: 
  • Build LLM-powered classification systems for messy SMB transaction data 
  • Improve RentFlow’s AI CFO for SMBs, turning financial data into actionable insights 
  • Power the landlord dashboard and AI insights, surfacing tenant health and portfolio trends
• Underwriting & risk: 
  • Analyze historical repayment data to identify key risk patterns and predictors 
  • Turn those insights into hard underwriting and risk rules 
  • Build a flexible decisioning framework to test and adjust rules over time 
  • Optional but highly appreciated: develop ML risk models to predict repayment and default risk
• Collaborate closely with the founders on product, risk, underwriting, and roadmap decisions 
• Shape the long-term architecture of RentFlow’s AI, ML, and data stack

You’ll Be a Great Fit If You 

• Have worked with LLMs in production and know where to apply them  
• Are comfortable working with messy financial data 
• Care about real-world impact 
• Enjoy high ownership, fast iteration, and ambiguous problem spaces 
• Want to help define the technical DNA of an early-stage company 
• Are excited to be an early hire with outsized impact, real equity, and real leverage on product and company direction

Why This Role Is Different 

• Your work will directly impact real money and real outcomes 
• You’ll help define an entirely new category at the intersection of rent, finance, and AI 
• You’ll work side-by-side with founders 
• You’ll have meaningful equity and real leverage from day one

If you want to build something with real stakes, real users, and real impact as an early hire, we’d love to talk! 

Interview Process

We do a simple and quick interview process consisting of 3 rounds:

1. Screening call to evaluate your experience and fit
2. Technical call to evaluate your skills
3. Debrief/Admin/Offer call