[{"@context":"https://schema.org","@type":"JobPosting","title":"VP of Operations","description":"

Flexible Compensation and Equity Options

Locations: San Francisco, CA and London, UK

About Corgi

Corgi is a full-stack insurance carrier building better, faster insurance products from the ground up. We're not just a broker: we design, underwrite, price, and issue policies directly, with fewer handoffs and less friction. Insurance is the largest unautomated industry in financial services, and we're rebuilding it using AI. We've raised $374M from Kindred, TCV, and others to do so. YC S24.

The Role

We are looking for a VP of Operations to build and lead the systems that make Corgi run. This is a hands-on leadership role for someone who enjoys creating order from complexity, scaling processes, and driving execution across a fast-moving business.

You will own operational strategy and execution across the company— ensuring teams, workflows, vendors, and core business operations function efficiently and scale alongside our growth. This role sits at the center of the organization and partners closely with leadership across insurance operations, finance, legal, people, and product.

We're not looking for someone who wants to manage from a distance. We want someone who can move between strategy and execution seamlessly— designing systems, solving problems, and helping the company operate at a high level every day.

What You'll Do

Own and improve company-wide operational systems and processes.
Build scalable workflows and operating infrastructure across teams and entities.
Chicago, IL | $125,000 - $200,000 | £60,000 - £90,000 | Equity Options
Corgi is vertically integrating the entire insurance industry. We design, underwrite, price, and issue insurance directly. Insurance is the largest unautomated industry in financial services, and we're rebuilding it from the ground up using AI. We've raised $374M from Kindred, TCV, and others to do so.
Building something great requires working hard. We are in the office 6-7 days a week. We are meritocratic with very high standards. If you don't meet them, you'll get cut. But if you deliver, you have unlimited scope to grow.
We move quickly, care deeply about talent density, and hire people who want to solve difficult problems with unusually high ownership.
As a Strategic Projects Associate, you’ll work across high-priority initiatives that help scale Corgi — from research and regulatory work to new initiatives, special projects, and cross-functional problem solving. You’ll partner closely with leadership and gain visibility into how a fast-growing company is built.

What You'll Do
- Support high-priority strategic initiatives across the business.
- Conduct research on markets, competitors, regulations, and emerging opportunities.
- Draft and organize written materials including analyses, filings, presentations, and internal documentation.
- Help evaluate and execute new projects, partnerships, and operational initiatives.
- Translate ambiguous problems into structured recommendations and action plans.
- Coordina","datePosted":"2026-06-01","employmentType":"FULL_TIME","hiringOrganization":{"@type":"Organization","name":"Corgi","sameAs":"https://www.ycombinator.com/companies/corgi-insurance/jobs"},"url":"https://jobs.ashbyhq.com/corgi/59ce4714-a929-441b-a1d3-bcf687ad10bb","jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"Chicago"}}},{"@context":"https://schema.org","@type":"JobPosting","title":"Business Development Representative ","description":"
  Business Development Representative
  Corgi is vertically integrating the entire insurance industry. We design, underwrite, price, and issue insurance directly. Insurance is the largest unautomated industry in financial services, and we're rebuilding it from the ground up using AI. We've raised $374M from Kindred, TCV, and others to do so.
  Building something great requires working hard. We are in the office 6-7 days a week. We are meritocratic with very high standards. If you don't meet them, you'll get cut. But if you deliver, you have unlimited scope to grow.
  We move quickly, care deeply about talent density, and hire people who want to solve difficult problems with unusually high ownership.
  What We're Looking For
  We’re hiring hard workers and fast learners. We are in-person only and full-time. The work is challenging, but we make it worthwhile. You are required to be in-office five days per week.
  What You’ll Do
  - Make outbound calls to startup founders and operators.
  - Set qualified meetings and join demos with AEs.
  - Own CRM hygiene and next steps until deals are closed.
  - Rewrite, test, and refine scripts in real time—keep what converts, kill what doesn’t.
  - Learn the startup insurance landscape quickly and speak confidently with founders.
  - Work closely with sales leadership to iterate on ICP, messaging, and outreach.
  What We’re Looking For

About Corgi

The Role

What You'll Do

What You'll Do

Business Development Representative

What You’ll Do

What We’re Looking For

Corgi

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