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

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

She will pick the best candidates from Jack's network.

The next step is to speak to Jack.

Job Title

Founding Machine Learning Engineer

Salary

$180k-$220k + Equity

Company Description

Withshepherd.com is a $42M Series B AI-native commercial insurance platform transforming how high-hazard industries get covered. Backed by Spark Capital and Y Combinator, they are building the risk infrastructure for the physical world, leveraging real-time data from partners like Procore to replace manual underwriting with fully autonomous, agentic ML systems.

Job Description

Join Withshepherd.com as their first Machine Learning Engineer to build the ML function from scratch. 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.

Location

San Francisco, USA

Why this role is remarkable

• Build an ML function from zero at a high-growth startup, defining the architecture, tooling, and evaluation frameworks that will shape the company's technical foundation.
• Work at the frontier of agentic AI, moving beyond simple chatbots to building fully autonomous systems that handle high-stakes financial decisions in the physical world.
• Join a well-capitalized Series B team with $60M+ in total funding from top-tier investors like Spark Capital, Costanoa Ventures, and Intact Private Capital.
  
  

What You Will Do

• 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.
  
  

The ideal candidate

• Has 4+ years of industry experience shipping production ML systems end-to-end, with deep proficiency in Python, PyTorch, and modern model deployment platforms.
• Possesses hands-on experience fine-tuning LLMs using techniques like RLHF or DPO and building reliable agentic workflows with structured outputs and tool use.
• Thrives in high-ambiguity, 0-to-1 environments and is committed to working on-site in San Francisco to collaborate directly with underwriters and engineers.
  
  

Who are Jack & Jill?

Ok, I'll go first. 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. 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.

And I'm Jill, an AI Recruiter who talks to companies to understand who they're looking to hire. Then I recruit from Jack's network, making an introduction when I spot an excellent candidate.

How does this work?

• Jack's an AI agent for job searching and career coaching. He works for you.
• Jill is the AI recruiter working for the company. She recruits from Jack's network.
• If it's a match and the company wants to meet you, they'll make the intro. In the meantime, if you'd like, Jack will send you excellent alternatives.
  
  

We never post fake jobs

This isn't a trick. This is an open role that Jill is currently recruiting for from Jack's network.

Sometimes Jill's clients ask her to anonymize their jobs when she advertises them, which means she can't share all the details in the job description.

We appreciate this can make them look a bit suspect, but there isn't much we can do about it.

Give Jack a spin! You could land this role. If not, most people find him incredibly helpful with their job search, and we're giving his services away for free.