Delivery Manager - Cloud & DevSecOps

Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London.

OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth.

OdysseyRe is rated A+ (Superior) by AM Best and AA- (Very Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH.

Delivery Manager – Cloud & DevSecOps

100% Remote
Contract-to-Hire Opportunity

Are you a strategic technology leader with deep domain experience and a hands-on approach to delivery? Do you excel at managing large-scale, cloud-native initiatives across global teams? Are you passionate about driving DevSecOps excellence and platform maturity in complex, regulated environments?

We are seeking a Delivery Manager – Cloud & DevSecOps to lead enterprise-scale transformations across cloud engineering, DevOps, and platform modernization. This role is ideal for a proven delivery leader who combines technical depth with business acumen, and who can operate confidently across executive stakeholders, engineering teams, and global delivery partners.

This is a high-visibility leadership role overseeing multi-million-dollar cloud programs, with direct responsibility for execution, team management, and customer success.

Key Responsibilities:

• Lead cross-functional teams of cloud engineers, DevOps architects, and delivery specialists, including third-party vendors and global delivery partners
• Own the execution of strategic cloud transformation programs—across Azure migrations, DevSecOps enablement, CI/CD optimization, and platform engineering initiatives
• Provide end-to-end delivery ownership: from roadmap planning and technical scoping through implementation, value realization, and post-go-live stabilization
• Drive customer retention, revenue assurance, and growth through delivery excellence and stakeholder trust
• Collaborate with enterprise architects, SRE leads, and product managers to align engineering outcomes with business goals and compliance needs
• Manage risks, budgets, and timelines across a $100M+ portfolio with a relentless focus on delivery quality and efficiency
• Influence technical direction and operational strategy, including design thinking workshops, change management, and continuous improvement
• Support business development and pre-sales efforts, including RFP responses, project scoping, and account expansion strategies
• Act as a trusted advisor to senior leadership, translating complex technical challenges into business-aligned delivery outcomes
• Lead Lean-Agile transformation efforts and ensure delivery practices align with DevSecOps and FinOps principles

Qualifications:

• 15+ years of experience in IT delivery, with a strong focus on cloud engineering, DevSecOps, and infrastructure modernization
• Significant leadership experience in insurance or InsurTech domains, managing complex global delivery programs
• Proven track record overseeing multi-million-dollar cloud initiatives with distributed teams and vendor partners
• Strong expertise in Azure cloud services, CI/CD tooling, SRE practices, and Infrastructure as Code (IaC)
• Deep understanding of compliance and regulatory standards in financial services (e.g., NIST, ISO 27001, HIPAA)
• Skilled in modern platform engineering, including internal developer platforms (IDP), observability, secrets management, and zero trust architecture
• Experienced in stakeholder management, executive reporting, and cross-functional collaboration at scale
• Prior consulting background and customer-facing delivery leadership preferred
• Excellent communication, presentation, and facilitation skills across technical and non-technical audiences
• Bachelor’s degree in Information Technology or related field; Master’s or certifications in cloud/security (e.g., Azure Architect, CKA, CISSP) a plus

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