Job Title: Senior Scrum Master (Contract) – Underwriting Platform Modernization
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
·Certified Scrum Master (CSM, PSM) required
·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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