Senior AI/ML Lead at RentFlow | Y Combinator

Senior AI/ML Lead

$130K - $200K•0.50% - 2.50%•San Francisco, CA, US / New York, NY, US / Remote (US)

Job type

Full-time

Role

Engineering, Machine learning

Experience

3+ years

Visa

US citizen/visa only

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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 ~3x MoM. 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 AI/ML lead to own underwriting, cash-flow intelligence, and data insights end-to-end.

This is a foundational role. You’ll design and ship models that make real financial decisions in production, affecting how and when business owners pay rent each month. You’ll work directly with the founders and have meaningful ownership over both technical direction and business outcomes.

What You’ll Do

• Model messy, real-world SMB cash flows from transaction-level data
• Build and iterate on underwriting & decisioning systems
• Leverage LLMs to surface unique insights into business owner behavior and the forces shaping cash flow beneath the surface
• Turn raw financial data into clear, natural insights for business owners and their partners
• Design signals that balance risk, growth, and user trust in real time
• Collaborate closely with founders on product, risk, and roadmap decisions
• Shape the long-term architecture of RentFlow’s AI & data stack

You’ll Be a Great Fit If You

• Have built and shipped ML or data-driven systems in production
• Have worked with LLMs in production and know where to apply them
• Are comfortable working with imperfect, noisy 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 models directly control 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!

We’re the first startup solving a hair-on-fire problem concerning 50%+ of small & medium businesses in the US, right at a moment when the data and infrastructure make it solvable at scale.

At the core of what we’re solving: business rent is fixed, business cash flow isn’t. That gap forces healthy businesses into monthly cash-flow stress and is a major driver of unnecessary business closures.

RentFlow turns fixed business rent into a cash-flow-synced product, underwriting it in real time from transaction-level data. This opens a $20B+ rent-splitting market and lets us expand into an 'AI CFO' cash-flow intelligence product for business owners and the platforms around them.

The product is live, growing ~3x MoM, and ramping up early partnerships with fast-growing SMB fintechs and property platforms.