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.

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 Advanced Scrum Master (SASM) is preferred
• Disciplined Agile Senior Scrum Master (DASSM) is preferred
• Certified SAFe 5/6 Scrum Master (SSM) is preferred
• Professional Scrum Master (PSM II or III) is preferred

#LI-MS

#LI-REMOTE

• Competitive compensation package
• Generous 401K employer match
• Employee Stock Purchase plan with employer matching
• Generous Paid Time Off
• Excellent benefits that go beyond health, dental & vision. Our programs are focused on your whole family’s wellness, including your physical, mental and financial wellbeing
• A core C&F tenet is owning your career development, so we provide a wealth of ways for you to keep learning, including tuition reimbursement, industry-related certifications and professional training to keep you progressing on your chosen path
• A dynamic, ambitious, fun and exciting work environment
• We believe you do well by doing good and want to encourage a spirit of social and community responsibility, matching donation program, volunteer opportunities, and an employee-driven corporate giving program that lets you participate and support your community

At C&F you will BELONG

If you require special accommodations, please let us know. We value inclusivity and diversity. We are committed to equal employment opportunity and welcome everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. If you require special accommodations, please let us know

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Crum & Forster is committed to ensuring a workplace free from discriminatory pay disparities and complying with applicable pay equity laws.  Salary ranges are available for all positions at this location, taking into account roles with a comparable level of responsibility and impact in the relevant labor market and these salary ranges are regularly reviewed and adjusted in accordance with prevailing market conditions. The annualized base pay for the advertised position, located in the specified area, ranges from a minimum of $110,800 to a maximum of $130,000. The actual compensation is determined by various factors, including but not limited to the market pay for the jobs at each level, the responsibilities and skills required for each job, and the employee’s contribution (performance) in that role. To be considered within market range, a salary is at or above the minimum of the range. You may also have the opportunity to participate in discretionary equity (stock) based compensation and/or performance-based variable pay programs.