Founding AI Engineer

Maestro

• $150K — $180K *
Finance & Insurance
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Experience delivering machine learning (ML) systems used by real users.
  • Strong software engineering skills beyond just prototyping.
  • Proficiency in operating and evaluating modern ML models in a production environment.
  • Ability to assess model quality, manage latency, and control costs effectively.
  • Practical mindset, focusing on the simplest solutions that work reliably.
  • Expertise in utilizing AI coding tools while maintaining engineering judgment.
  • Local to San Francisco for daily in-office collaboration.

Responsibilities

  • Build production-level AI systems for complex financial workflows.
  • Develop models and data pipelines for analyzing unstructured and structured financial information.
  • Design evaluation metrics to measure AI system quality and performance.
  • Create feedback mechanisms to enhance models based on customer interactions.
  • Select appropriate model types including foundation, specialized, or deterministic models.
  • Continuously ship software, monitor its performance, and refine it based on user feedback.
  • Establish ML infrastructure and standards for future engineers to follow.

Benefits

  • Opportunity to work closely with experienced founders and industry leaders.
  • Engagement in transforming the commercial real estate industry with innovative technology.
  • Chance to build foundational systems for a new product in an emerging market.
  • Work environment that encourages quick iteration and deployment based on customer needs.
  • Involvement in a well-funded startup with backing from notable venture capitalists.
Full Job Description
The commercial real estate space is ripe for disruption. The industry has exploded in size and revenue, but still runs on fragmented CRMs, legacy loan systems, email, spreadsheets, phone calls, and document portals. Legacy players are struggling to adapt to an AI-native age, while lenders and brokers are constrained by manual work.

We're going to change that.

We're building an autonomous loan origination and processing platform that helps commercial real estate lenders move loans from intake through underwriting with no manual work. We're:
  • An experienced team used to shipping fast - with alumni and tech leads from Meta, LinkedIn, and Rippling.
  • Backed by a16z through Speedrun.
  • Working with multiple paid pilots, and moving quickly from customer conversations to production software.


The Role

We're looking for a founding AI/ML engineer to build the intelligent systems at the heart of our product.

You'll work directly with the founders and customers and own the full production loop: data, model selection and adaptation, evaluations, serving, monitoring, and iteration. You'll turn messy, real-world financial information into reliable decisions and actions.

You'll:
  • Build production AI systems for complex, high-stakes workflows
  • Develop models and pipelines for understanding unstructured and structured financial data
  • Design evaluation systems that measure quality, reliability, latency, and cost
  • Build feedback loops that turn customer usage into better models and products
  • Decide when to use foundation models, specialized models, deterministic systems, or a combination
  • Ship constantly, observe real-world performance, and iterate with customers
  • Establish the ML infrastructure and standards that future hires inherit
What We're Looking For
  • Evidence that you've shipped ML systems that real users touched
  • Strong software engineering fundamentals beyond notebooks and prototypes
  • Experience evaluating, adapting, and operating modern models in production
  • Sound judgment about model quality, failure modes, latency, and cost
  • Pragmatism: you use the simplest approach that reliably solves the problem
  • Fluency with AI coding agents and the ability to use them without outsourcing your engineering judgment
  • Live in San Francisco and are available to work in person with the team 5 days a week.

Experience with Python, PyTorch, model serving, LLMs, retrieval, document intelligence, or multimodal systems is helpful, but the ability to learn and execute matters more. You don't need prior experience in lending or commercial real estate.

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