Founding Forward Deployed Engineer

San Francisco, CA (in-person)Founding (hire #3–#5)$165k–$200k + 0.2% - 1%

Circle — "Circle picks up calls, sends emails, and fills portals while you close."

Why Circle?

Insurance runs on people doing heroic amounts of manual work. We're changing that.

At Circle, we're bringing the world's most advanced AI into insurance brokerages and automating 90% of the manual work that insurance brokers do—from the mind‑numbing, error‑prone steps to the multi‑system swivel‑chair tasks that slow everything down. The result: quotes go out faster, renewals run themselves, and producers get their day back.

We're a small, product‑obsessed team shipping fast with real customers. You'll work directly with the founders, own outcomes, and see your code move the industry forward in weeks—not quarters.

The Role

As our Founding Forward Deployed Engineer, you are the technical face of Circle with customers. You'll sit with users, map messy workflows, and turn them into production‑grade automations. Think rapid prototyping → first demo in days → hardening into reliable, observable systems. You'll thrive if you love ambiguity, enjoy hopping between product and code, and measure success by what's running in the wild.

What You'll Do

Own customer outcomes end‑to‑end: scope → build → deploy → iterate with real users

Ship high‑leverage automations: orchestrate LLM‑powered agents, integrate phones/email, and drive browser‑based flows for web portals—without needing perfect APIs

Integrate systems pragmatically: connect to CRMs/AMSs, document stores, and queues; design for retries, idempotency, and observability

Prove value fast: stand up pilots, instrument success (cycle time, accuracy, reliability), and turn wins into repeatable playbooks

Partner on GTM: help run workshops, demos, and proof‑of‑value with prospects and early customers

In Your First 30 Days, You Might

Shadow producers and account managers, capture a high‑friction workflow, and ship a first pass that cuts cycle time by 30–50%

Build a resilient headless‑browser task with robust auth/session handling and structured logging

Stand up metrics that let customers see time saved and errors avoided

What Will Make You Successful

Builder's bias: you've shipped production systems in scrappy environments and can demo progress early and often

Customer fluency: you like sitting with users and turning fuzzy requests into running code

Technical range: Fluency across key domains: TypeScript/Next.js, Node.js, Python, APIs & queues, headless browser automation, LLM/AI agent orchestration, cloud/CI/CD, and observability with logs/metrics/traces

Sound engineering judgment: failure modes, retries, data hygiene, and security are second nature

Nice‑to‑Have

Experience in B2B workflow automation

Voice/email integrations experience

Working around imperfect third‑party systems

How We Work

Small team, big ownership

You'll make architectural calls and set quality bars.

Ship fast, then harden

First demo in days, then productionize with reliability and observability.

In-Person in SF

We work 6 days a week in our SF office.

Compensation & Benefits

Base salary: $165k–$185k (up to $200k for exceptional fit)

Equity: 0.2%–1% ISOs

Benefits: Medical/Dental/Vision (employee‑friendly coverage) + latest MacBook Pro

Phone/data stipend, learning budget, and travel as needed for customer work

Small team, big ownership: You'll make architectural calls and set quality bars

Ship fast, then harden: First demo in days, then productionize with reliability and observability

In-Person in SF: We work 6 days a week in our SF office with coffee, snacks, and a great community.

Our Process

Founder intro

(45m)

Mission, your story, mutual fit

Technical deep dive

(90m)

Systems you've built, tradeoffs, failure modes

Co-working session

(2–3h)

Build a small automation against a mock portal

Customer empathy chat