Delivery Lead, IT - Scrum (Remote)

Crum & Forster Company Overview

Travel Insured International, a Crum & Forster company, is seeking a Delivery Lead to oversee the successful planning, execution, and release of key product features within Agile delivery trains. This role is a blend of Scrum Master, Agile Coaching, Release Management, and Delivery Coordination. The Delivery Lead will work closely with Scrum Teams, DevOps, QA, and business stakeholders to ensure smooth execution, from sprint planning to production release.

Travel Insured International is a leading travel insurance provider with more than 30 years in business. As a key component of our Specialty Business Unit, within the Accident & Health division, TII provides travel protection plans to help each individual travel confidently. Travel Insured International is proud to offer products to consumers and to agency partners of all sizes. We're committed to providing dependable coverage, great value, and end-to-end satisfaction for all customers.

This individual will play a critical role in facilitating Agile ceremonies, coordinating technical delivery (including infrastructure and CI/CD pipeline readiness), managing dependencies, and ensuring that quality assurance processes are properly executed. The Delivery Lead will also partner with Product Owners and business stakeholders to ensure UAT planning and release readiness.

 

Job Description

What you will do:

 

 

Agile & Scrum Leadership

• Facilitate Sprint Planning, Daily Stand-ups, Sprint Reviews, and Retrospectives for assigned delivery teams.
• Ensure teams follow Agile best practices and drive continuous improvement in Agile maturity.
• Coach Product Owners on backlog refinement, prioritization, and writing effective user stories.
• Remove blockers, dependencies, and inefficiencies that impact sprint execution.

Delivery & Release Management

• Own the end-to-end feature delivery process, ensuring on-time, high-quality releases.
• Collaborate with Product Owners, Business Stakeholders, and Tech Leads to define and prioritize deliverables.
• Define release schedules, ensuring coordination across multiple teams and stakeholders.
• Manage release entry and exit criteria, partnering with Business/Department Stakeholders to validate requirements and define UAT timelines.
• Ensure UAT testing is scheduled and executed, coordinating efforts with stakeholders.
• Facilitate release go/no-go decisions and ensure all dependencies are addressed before deployment.

CI/CD & Environment Readiness

• Coordinate environment setup and configurations, working with DevOps engineers to ensure proper infrastructure readiness.
• Assist in managing Azure Pipelines and Infrastructure as Code (IaC) builds to streamline deployments.
• Ensure environment stability for development, testing, and release processes.

Quality Assurance & Testing Oversight

• Work closely with QA Test Leads and Testers to ensure test plans and test cases are created and executed.
• Facilitate test strategy discussions, ensuring proper coverage for unit, integration, regression, and user acceptance testing.
• Monitor defect tracking and resolution to prevent delays in the delivery timeline.

Stakeholder Communication & Risk Management

• Act as a bridge between business, technical teams, and leadership, ensuring alignment on delivery timelines.
• Identify and mitigate risks impacting sprint or release timelines.
• Provide regular progress updates to executives, business leaders, and delivery teams.
• Ensure transparency by leveraging Agile delivery tools (e.g., Jira, Azure DevOps, Rally).

 

What YOU will bring to C&F:

 

 

• A college degree or equivalent experience is required
• 8+ years of experience in Agile software delivery roles such as Scrum Master, Agile Delivery Manager, or Release Manager is required
• Strong expertise in Scrum, SAFe (Scaled Agile Framework), and Disciplined Agile Delivery (DAD) is required
• Certified Scrum Professional – Scrum Master (CSP-SM) is required
• Proven experience with release management, UAT coordination, and CI/CD pipeline integration.
• Experience working with Azure DevOps, Jira, and Infrastructure as Code (IaC) for deployments.
• Deep understanding of QA processes, test case management, and defect resolution workflows.
• Excellent facilitation, problem-solving, and servant-leadership skills.
• Strong ability to collaborate across technical and business teams to drive outcomes.
• SAFe Adv