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Weekend Chief Underwriting Officer Jobs (NOW HIRING)

Westfield

Specialty Senior Underwriter

Berkeley Heights, NJ · On-site

$102K - $121K/yr

Reporting to the Chief Underwriting Officer A&H, you will be a key contributor to the overall management, growth, and profitability of our business. * Lead our entry into new products and markets ...

Westfield

Specialty Senior Underwriter

Berkeley Heights, NJ · On-site

$102K - $121K/yr

Reporting to the Chief Underwriting Officer A&H, you will be a key contributor to the overall management, growth, and profitability of our business. * Lead our entry into new products and markets ...

Westfield

Specialty Underwriter

Berkeley Heights, NJ · On-site

$100K - $170K/yr

Reporting to the Chief Underwriting Officer A&H, you will be a key contributor to the overall analysis and management of our new and renewal business. * You will work directly with brokers to ...

Westfield

Specialty Underwriter

Berkeley Heights, NJ · On-site

$100K - $170K/yr

Reporting to the Chief Underwriting Officer A&H, you will be a key contributor to the overall analysis and management of our new and renewal business. * You will work directly with brokers to ...

Awac

AVP, Underwriting - Environmental

Los Angeles, CA

$130K - $175K/yr

Liaise with Chief Underwriting Officer, actuary, claims, accounting, IT and legal departments as appropriate. Manage and delegate authority. Job Qualifications: * At least 7 years relevant ...

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Weekend Chief Underwriting Officer information

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$41.5K

$151.2K

$269.5K

How much do weekend chief underwriting officer jobs pay per year?

As of Sep 7, 2026, the average yearly pay for weekend chief underwriting officer in the United States is $151,203.00, according to ZipRecruiter salary data. Most workers in this role earn between $111,500.00 and $185,000.00 per year, depending on experience, location, and employer.

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Weekend Chief Underwriting Officer jobs near you

Founding Platform Engineer (Fulltime - Hybrid)

Cleo Consulting

New York, NY • On-site

Contractor

Re-posted 5 days ago

Job description

Job Title: Founding Platform Engineer
Location: New York City
Fulltime - Hybrid

About Client

  • Client is an AI-native, full-stack specialty insurance carrier built to operate like a quantitative hedge fund rather than a traditional insurer. Client owns its own balance sheet and organizes around small, autonomous product pods - each pod finds an underserved or entirely new insurance market, builds a differentiated underwriting strategy on proprietary data and ML pricing models, and runs its own book and P&L once cleared through Client's internal research and validation gates.
  • Client has raised $107M in seed capital. First products are expected to go live in under 90 days, with the business targeting cash-flow positive in year one and the first five products funded off balance sheet.
  • Founded by Benjamin Markoff (CEO) - who built and exited Founder Shield (insurtech, nine-figure gross written premium, acquired by The Baldwin Group in 2021), the tech-enabled MGA Scale Underwriting, and Broker Buddha (exited January 2023) - and Judah Sosnick (CTO), a founding engineer at an enterprise AI/prediction-modeling startup who went on to build a systematic equities trading platform and served as CTO of an entertainment holding company deploying LLMs and agentic AI. The team will stay intentionally small (tens, not hundreds, of employees), so every hire is load-bearing.

About the Role

  • This role sits above the product pods rather than inside any one of them, owning the internal underwriting operating system that every pod builds on top of - the data backbone, model serving, experimentation and backtesting, underwriting workbenches, and agentic research workflows that have to carry each new insurance opportunity through Client's stages of conviction and validation.

Key Responsibilities

  • Own and build the central data backbone: ingestion, transformation, and governance across highly varied specialty-insurance data sources.
  • Build and operate model deployment and serving infrastructure for pricing and underwriting models.
  • Build product experimentation and backtesting systems that let pods validate a new insurance strategy before committing capital.
  • Build human and AI-assisted underwriting workbenches used directly by underwriters and pod leads.
  • Build agentic workflows for research, demand signaling, and distribution validation ahead of a product launch.
  • Build audit, governance, and compliance flows across the platform.
  • Sit with the CEO, CTO, and Chief Underwriting Officer to translate business requirements into technical specs, then lead execution.

Requirements

  • Has built a highly configurable, end-to-end internal workbench or platform before, not a customer-facing product.
  • Systems and architecture background from an AI lab, big tech company, or startup building the workflows and infrastructure around ML products, not necessarily the models themselves.
  • Comfortable prioritizing architecture and functionality over visual polish, since this is internal tooling.
  • Enterprise-grade instincts for data-intensive, model-intensive, agent-driven systems.

Bonus Skills

  • Product management experience at a big tech company, or strong product instincts and fluency (confirmed nice-to-have, not required) - this person will take a business requirement directly from the CEO, CTO, and Chief Underwriting Officer and translate it into what gets built.

Logistics

Location

  • New York City, hybrid - flexible for A+ talent. Tri-State-based candidates: 2-3 days/week in-office. Candidates based elsewhere: roughly one week per month in NYC. Open to candidates relocating to the NYC area.

Benefits/Other

  • No visa sponsorship - candidates must already have US work authorization.
  • Founding equity on this seat.

Interview Process

  • Interview with CEO.
  • Interview with CTO.
  • Take-home project, with a 48-hour turnaround.

“Cleo Consulting is an equal opportunity employer (Minorities/Women/Veterans/Disabled)”