Staff Software Engineer – Stop-Loss Platform

Oliver James Group; United States; Remote; USD 140,000 - 210,000; Full time

Job summary

Oliver James Group is partnering with a leading insurance organization to hire a Staff Software Engineer to design and build a brand-new Stop-Loss platform from the ground up. You will act as a technical authority, setting architecture and engineering standards, evaluating vendor platforms, and leading an AI-first development approach while remaining hands-on in code.

Expect to shape wide platform design as the team grows and to mentor engineers in a regulated, data-sensitive environment.

Qualifications

• AWS hands-on experience designing, building, and running production workloads on AWS.
• Vendor management: evaluating third-party platforms, directing vendor/offshore teams, ensuring scope/quality.

Responsibilities

• Act as the technical authority for the Stop-Loss platform, defining architecture, standards and best practices.
• Evaluate and adapt a vendor platform, providing technical direction to vendor/offshore engineers.
• Drive an AI-first approach across infrastructure and applications built on the core platform.
• Design and build a highly event-driven platform to support workflows like RFPs, claims and other events.
• Own core platform foundations: data ingestion, backend services, database design and schemas, semantic layer, GraphQL infra.
• Mentor engineers as the team grows.
• Work with sensitive data (PII/PHI) in a secure, scalable environment.

Skills

AWS

Vendor management

AI experience

C#/.NET

React

Python

GraphQL

Communication

Job description

Staff Software Engineer - Stop-Loss Platform | Contract to Hire | No Sponsorship offerd

We're currently partnering with a leading insurance organization on their search for a Staff Software Engineer to help build a brand-new Stop-Loss platform from the ground up.

This isn't simply a feature-development role. You'll act as a technical authority on a greenfield platform, setting the architecture and engineering standards while staying hands-on in the code.

The initial focus will be evaluating a vendor platform, determining which components fit the organization's Stop-Loss requirements and which don't, and then building on top of what's usable. As the internal engineering team is established, you'll shape how the wider platform is designed and delivered, with an AI-first approach.

Essential requirements (all three are must-haves):

• AWS: hands-on experience designing, building, and running production workloads on AWS.
• Vendor management: proven experience evaluating third-party platforms, directing vendor and offshore teams, and holding them to scope and quality, not just tracking status.
• AI: practical experience building with or on AI (LLMs, agents, or AI-enabled applications) and using AI-assisted development tools.

What we're looking for:

A strong, hands-on Staff Engineer who is comfortable being opinionated and making technical decisions, not simply following them. You should be able to move between architecture and implementation and still write production code.

In addition to the essentials above, a strong background in C#/.NET and React, with proven experience in platform architecture, layered system design, and event-driven systems. Python and GraphQL are valuable, but we care more about sound engineering judgment than a technology checklist.

Strong communication skills. You'll be working closely with senior stakeholders and explaining technical decisions clearly.

Experience in Insurance, Financial Services, or another regulated environment is desirable, particularly where you've handled sensitive data (PII/PHI).

Key responsibilities include:

• Acting as the technical authority for the Stop-Loss platform, defining how things are built and setting engineering standards and best practices.
• Evaluating, adapting, and building on top of a vendor platform, and providing technical direction to vendor and offshore engineers.
• Driving an AI-first approach, including the infrastructure and applications built on top of the core platform.
• Designing and building a highly event-driven platform supporting workflows such as RFPs, claims, and other business events.
• Owning core platform foundations, including data ingestion, backend services, database design and schemas, the semantic layer, and GraphQL infrastructure.
• Mentoring engineers as the team grows.
• Working with sensitive data, including PII and PHI, within a secure and scalable environment.

Why this role is different:

You're joining at the very beginning of a new engineering capability. The plan is to build a team around the platform, including Senior Engineers and DevOps, giving you the chance to shape both the platform and how the engineering function works, with a clear path to growing into team leadership.