Jack & Jill

Jack & Jill

Founding Machine Learning Engineer ($180k-$220k + Equity) at Withshepherd

San Francisco, California

Sponsorship not specified$180k-$220kDetected 25 days ago
PythonAWSMachine LearningPyTorchSparkData EngineeringLLMsAgentic AIMLOpsUnderwriting

About the role

  • She will pick the best candidates from Jack's network.
  • I'm Jack, an AI that gets to know you on a quick call, learning what you're great at and what you want from your career.
  • And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire.

Responsibilities

  • Own the end-to-end ML lifecycle, from designing raw data pipelines and training fine-tuned models to deploying and monitoring production systems on AWS Sagemaker.
  • Build and close feedback loops that convert human underwriter domain expertise into training signals, enabling continuous model improvement and autonomous capability progression.
  • Develop advanced evaluation frameworks and confidence scoring systems to safely scale LLM-driven agentic workflows across the entire commercial underwriting lifecycle.
  • Possesses hands-on experience fine-tuning LLMs using techniques like RLHF or DPO and building reliable agentic workflows with structured outputs and tool use.
  • Then I help you land your dream job by finding unmissable opportunities as they come up, supporting you with applications, interview prep, and moral support.

Requirements

  • Has 4+ years of industry experience shipping production ML systems end-to-end, with deep proficiency in Python, PyTorch, and modern model deployment platforms.
  • The ideal candidate

Compensation

  • Company Description
  • Withshepherd.com is a $42M Series B AI-native commercial insurance platform transforming how high-hazard industries get covered.
  • Job Description
  • You will design, train, and deploy production systems that automate complex underwriting workflows.
  • This high-ownership role focuses on advancing the platform toward fully autonomous insurance decisions, leveraging LLMs and agentic frameworks to transform how construction and industrial risks are priced and managed.
  • San Francisco, USA

Benefits

  • Founding Machine Learning Engineer
  • $180k-$220k + Equity
  • Join Withshepherd.com as their first Machine Learning Engineer to build the ML function from scratch.

Company info

  • This is a job that Jill, our AI Recruiter, is recruiting for on behalf of one of our customers.

This listing is sourced directly from Jack & Jill's careers page and normalized into a canonical job model.