Location : Remote
Type : Contract (W2 or C2C)
Duration : 6 months with likely extension
Industry : Insurance Technology / Digital Transformation
Project Overview :
We are seeking an experienced Senior Scrum Master (Contract) to support the modernization of a core underwriting platform for a mid-sized insurance carrier undergoing digital transformation. The project is focused on reengineering legacy processes and platforms, integrating CI / CD pipelines, and implementing robust automated testing frameworks to enable faster, more reliable software delivery.
This is a contract opportunity ideal for a seasoned Agile practitioner who has helped insurance or financial services firms transition toward more modern engineering practices. We have several staff already working at the client and have a direct and longstanding relationship with them.
Key Responsibilities :
- Facilitate Scrum ceremonies (daily stand-ups, backlog grooming, sprint planning, demos, retrospectives) for cross-functional development and QA teams
- Coordinate closely with DevOps and QA leads to embed CI / CD and automated testing into the development lifecycle
- Ensure consistent, high-quality delivery of sprint objectives within the context of an evolving platform and infrastructure
- Help teams define and enforce Definition of Done , with a strong emphasis on integration, regression, and UAT readiness
- Act as a servant leader to clear blockers, manage team health, and support delivery in a high-change environment
- Collaborate with business analysts, product owners, and architects to break down complex requirements tied to legacy platform replacement
- Coach the team and stakeholders on Agile best practices tailored to hybrid legacy-modern delivery
- Provide clear reporting on sprint metrics, risks, and delivery status to internal IT leadership and external consulting partners
- Manage cross-team dependencies and timelines within a broader transformation roadmap
Required Qualifications :
- 7+ years as a Scrum Master with demonstrated success in complex Agile delivery environments
- Prior experience supporting insurance carriers or financial institutions through core platform modernization or digital transformation
- Proven experience implementing or operating within CI / CD pipelines (e.g., Jenkins, GitLab, Azure DevOps) and integrating test automation into Agile workflows
- Comfortable working across QA, DevOps, product, and legacy IT teams to harmonize delivery efforts
- Background in transitioning teams from waterfall or hybrid SDLC models to Agile / DevOps
- Strong working knowledge of Jira, Confluence, and sprint performance metrics
- Excellent communication and stakeholder management skills in matrixed environments
Nice to Have :
- Experience with underwriting systems or insurance platforms (e.g., Guidewire, Duck Creek, or homegrown policy admin systems)
- Familiarity with containerization, microservices, and API testing
- Experience with regulatory / compliance frameworks common in insurance (SOX, NAIC, etc.)
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