Forward Deployed Operations

About the role

You will spend your days translating the messy reality of how insurance actually works into the clean systems that make it scale. This role owns the critical bridge between the operators who live in the trenches and the builders who create the tools. You will synthesize disconnected streams of information, from customer frustrations to operational bottlenecks, into a single, sharp read on the most important problem to solve next. You will then build the thing that solves it, moving from insight to implementation with speed and ownership. The hire will run the operation while simultaneously improving the operation, ensuring that every automation directly moves a business metric. You will develop genuine empathy for the people doing the work and use that understanding to build tools they actually adopt. Ultimately, you will be responsible for turning opaque, manual expertise into reliable, automated leverage that compounds over time.

Key facts

What you'll do

• Find the leverage by sitting with operators and watching the work to surface automations that nobody built because nobody knew they were possible yet.
• Run the operation by handling underwriter follow-ups, carrier communications, and customer calls to keep deals moving through the pipeline.
• Build fast by prototyping AI agents, internal tools, and workflow automations in days and shipping them in weeks.
• Instrument everything by writing SQL, pulling the data, and building dashboards that prove what you shipped moved a number in business terms, not feature terms.
• Shape what gets built next by translating operational pain into clear product requirements that engineering can act on immediately.
• Move where it is urgent by context-switching across functions based on what matters most this week, ignoring rigid org charts.
• Own the messy end-to-end lifecycle of a problem, from initial discovery through implementation and measured impact.
• Communicate outcomes to both technical and non-technical audiences, explaining why a number moved and why it matters.

Requirements

You must have shipped internal tools or automations end-to-end, not just designed them on a whiteboard.

You must have also run real operations, whether customer-facing or process-heavy, and know what it feels like when a system breaks at 7 AM.

You must measure yourself in business outcomes, such as "conversion went up 15%," rather than merely noting that a feature shipped.

You must be able to walk into a room of non-technical operators, explain why a number moved, and earn their trust immediately.

You must prefer owning a messy problem end-to-end over executing a clean task that someone else handed to you.

You must have been exceptional at something before and be looking for a place that finally matches your ceiling.

You must have 2-4 years in a high-pace environment such as a startup, operations role, or consulting engagement.

You must have a track record of building and shipping things that ran in production, including internal tools, automations, or workflows.

You must be comfortable with SQL and at least one of Python or TypeScript.

You must have hands-on experience with AI coding tools like Cursor, Claude Code, or equivalent, not just awareness of them.

You must possess strong written and verbal communication skills with both technical and non-technical audiences.

You must be based in San Francisco or willing to relocate immediately.

Nice to have

Experience with LLMs, AI agents, or voice AI.

A background in insurance, fintech, or another regulated, high-stakes industry.

Prior startup or founder experience.

Solutions engineering, operations, or customer success experience.

Practical notes

This role is on-site in San Francisco, in person, with long days required five days a week.

A real share of the week involves follow-ups, chasing, coordination, and cleanup - the operational backbone done well.

Ambiguity is the job, not a phase; scope shifts week to week, and fixed lanes with clean specs are not provided.

The ceiling is high and real, with paths to running functions, leading teams, or starting companies for exceptional people.

The schedule includes Monday-Friday with a very early morning start in-office five days a week.

Benefits include Uber commuter benefits, breakfast, lunch, and dinner provided, daily snacks and drinks, free gym membership, and health, dental, and vision insurance.

The process begins with a 15-minute founder call.