Delivery Manager - Cloud & DevSecOps

Odyssey

13d•Remote

About The Position

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% RemoteContract-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.

Requirements

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
Excellent communication, presentation, and facilitation skills across technical and non-technical audiences
Bachelor’s degree in Information Technology or related field

Nice To Haves

Prior consulting background and customer-facing delivery leadership preferred
Master’s or certifications in cloud/security (e.g., Azure Architect, CKA, CISSP) a plus

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