Founding Director, Enterprise Sales
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
You've spent years in insurance—you know the language, the workflows, and the pain. Now use that expertise to sell the solution. As our Founding Director of Enterprise Sales, you'll own the full sales cycle: prospecting brokerages, running demos, negotiating contracts, and closing deals. You're not just selling software—you're selling a vision of what insurance operations could be, and your industry credibility makes that pitch land.
What You'll Do
Own the sales pipeline: Prospect, qualify, and close deals with independent P&C brokerages
Run the sales process end-to-end: Discovery calls, demos, proposals, contract negotiation, and close
Build relationships: Leverage your insurance network and credibility to open doors and build trust
Develop sales playbooks: Document what works, refine messaging, and create repeatable processes
Partner with founders: Shape pricing, packaging, and go-to-market strategy based on what you hear from prospects
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
Insurance background: 3+ years at an insurance brokerage, carrier, or MGA—you speak the language fluently
Sales experience: Track record of closing deals, whether in insurance or a related B2B context
Relationship builder: You know how to earn trust and navigate complex buying decisions
Startup mindset: Comfortable with ambiguity, self-directed, and energized by building something from scratch
Nice‑to‑Have
Experience at a top 100 independent brokerage
Existing relationships with brokerage principals or operations leaders
Familiarity with AMS platforms (AMS360, HawkSoft, Applied Epic)
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: $130k–$155k (up to $170k for exceptional fit) + commission
Significant equity package (founding role)
Benefits: Medical/Dental/Vision coverage
Build the sales function from the ground up
Direct access to founders and influence on company direction
In-Person in SF: Monday–Friday in our SF office with coffee, snacks, and a great community.
Our Process
Founder intro
(45m)Mission, your story, mutual fit
Technical deep dive
(60m)Systems you've built, tradeoffs, failure modes
Co-working session
(2–3h)Build a small automation against a mock portal
Apply for Founding Director, Enterprise Sales
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