Delivery Lead

Odyssey

1d • 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 Lead100% Remote6 months contract to hire Are you an IT quarterback? Do you have a passion for building high performing teams? Do you get energy from surgically moving the football down the field? We are seeking an experienced IT Delivery Lead to join a high-performing technology team within a fast-paced, regulated environment. These roles are ideal for professionals who thrive in ambiguity, enjoy solving complex business challenges, and can drive initiatives from concept to production. Candidates must be confident, collaborative, and delivery-oriented, with a consultative mindset and a strong understanding of both business and technology. This is a hands-on leadership opportunity for individuals who are comfortable operating across all phases of the project lifecycle — from business engagement and requirements gathering, to solution planning, technical coordination, testing, go-live, and post-production support.

Requirements

• 7–10 years of progressive experience in IT delivery, solution leadership, or technical consulting
• Broad exposure across project management, architecture, software engineering, QA, and business analysis
• Hands-on experience delivering modern infrastructure initiatives such as Azure Virtual Desktop migrations or security platform upgrades
• Proven ability to lead without authority and influence cross-functional teams
• Experience in Agile environments and familiarity with SDLC best practices
• Excellent interpersonal, listening, and written communication skills
• Confident in stakeholder-facing roles, with the ability to present to executive audiences
• Strong critical thinking, facilitation, and problem-solving skills
• Comfortable operating in high-pressure, ambiguous environments
• Bachelor’s degree in Information Technology or related field preferred

Nice To Haves

• Prior consulting experience (Big 4 or equivalent) strongly preferred

Responsibilities

• Act as a strategic partner to business stakeholders and IT leadership by translating business needs into actionable technology initiatives
• Engage directly with internal customers to gather feedback, assess issues, and ensure continuous service improvement
• Drive early project phases including requirements elicitation, persona development, and business case creation
• Facilitate stakeholder interviews and develop voice-of-customer surveys to identify pain points and prioritize opportunities
• Create and present project charters, plans, and risk assessments to cross-functional committees
• Lead delivery execution, including vendor coordination, POCs, and the full SDLC: build, configure, test, deploy, stabilize
• Develop and implement user acceptance testing (UAT) and change management strategies to ensure successful adoption
• Collaborate with engineering, architecture, QA, and PM teams to align solution design with business needs and technical standards
• Maintain ongoing ownership of assigned initiatives, including continuous improvement and post-launch support activities

What This Job Offers

• Career Level: Mid Level
• Number of Employees: 251-500 employees