IT Recruiter & Contingent Workforce Specialist

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.

Overview

We are seeking an experienced Recruiter with 4-7 years’ in-house or agency recruitment experience within financial services, with a strong track record hiring for IT / technology roles (both permanent and contract). A key part of this role is owning the contractor lifecycle; ensuring all processes, controls and procedures are followed, and that contractor records and compliance are accurately maintained.

Talent Acquisition

• Manage end-to-end recruitment for Odyssey Group and Re North America, including permanent and temporary roles.
• Partner with hiring managers to define requirements, create job descriptions, and agree on sourcing and selection strategies.
• Educate stakeholders on recruitment and contractor policies, processes, and best practices.
• Build strong relationships with hiring managers and department heads across functions.
• Source candidates via LinkedIn, job boards, referrals, agencies, and talent pools.
• Screen resumes, conduct initial interviews, and manage candidate shortlists.
• Coordinate and schedule interviews, gather feedback, and manage the offer process.
• Provide market insights on salary, skills availability, and competitor hiring trends within the (re)insurance/financial services industry.
• Manage relationships with approved recruitment agencies, ensuring adherence to agreed terms, compliance requirements, and performance standards.
• Attend meetings, lunches, dinners, and business functions with vendor partners to maintain strong business relationships.

Contractor Management, Tracking & Compliance

• Act as primary contact for all IT contractors from onboarding through offboarding and/or contract-to-hire. Ensure all contractor processes are followed (approvals, on-boarding checks, documentation, renewals).
• Partner with procurement to negotiate terms for cost efficiency, termination clauses, and favorable conditions for new vendors and renewals.
• Manage vendor relations from procurement through on-boarding and termination. Manage contract terms. Obtain all required documentation for new vendors (NDA, MSA, SOW, banking instructions) and upload new vendors into Contract Logix for historical tracking.
• Maintain an accurate contractor register (rates, start date, extensions, end dates, assignment changes) in NERM; track assignment end dates and proactively manage extensions, renewals, and terminations.
• Understand contract-to-hire terms – full time placement cost, salary, benchmark data.
• Ensure compliance with background checks, right-to-work and KYC (Know Your Customer) requirements (where relevant), and other applicable regulations.
• Monitor contractor performance and engagement through regular check-ins with managers and contractors.

NERM Management

• Advise vendors of contract terminations and provide data to support contractual obligations.
• Support managers in updating NERM and approve those updates.
• Manage the Contract Tracker by memorializing all relevant contractual data (vendor, contract titles, dates, cost, department, rationale).
• Work with vendor partners to obtain data for onboarding and enter/approve NERM entries in a timely manner.
• Support managers in submitting tickets where contractors require additional access.
• Approve IT tickets for access not set up via SailPoint.

Process, Systems & Reporting

• Use ATS and HR systems to maintain accurate data, candidate tracking, and hiring metrics.
• Run and maintain dashboards and reports covering the recruitment pipeline, time‑to‑hire, contractor headcount, rates, and tenure, and manage and deliver people metrics including cost per hire, contractor extensions, and conversion rates.
• Continuously review and improve recruitment and contractor management processes for efficiency, compliance, and stakeholder experience.
• Ensure documentation and workflows are current and aligned with internal policies and financial services regulatory requirements.

Qualifications & Experience

• 4-7 years of recruitment experience, with a focus on IT/technology roles.
• Experience within financial services (banking, insurance, asset management, or tech firm).
• Strong track record recruiting both permanent and contract/contingent hires.
• Demonstrated experience managing and tracking contractors, including extensions, offboarding, and compliance processes.
• Familiarity with recruitment and contractor compliance (right-to-work, background checks, worker classification or equivalents, data privacy).
• Proficiency with ATS and HR/recruitment tools.
• Strong stakeholder management, influencing, and communication skills.
• High attention to detail, especially in data tracking, documentation, and process adherence.
• Ability to manage multiple requisitions and contractors simultaneously.
• Strong organizational and time management skills
• Customer-focused mindset, balancing candidate experience with business needs and regulatory requirements.
• Analytical and data-driven in tracking performance and contractor metrics.
• Proactive, solutions-driven, and comfortable challenging stakeholders when processes are not followed.

Desirable

• Knowledge of local labor and contractor laws in relevant jurisdictions.
• Professional qualifications or training in recruitment/HR (e.g., CIPD, AIRS, LinkedIn Recruiter certification).

#LI-Hybrid

This role can either be hybrid in Stamford or be fully remote if employee is in the tri-state area and willing and able to visit the Stamford, CT office once a quarter.

We are an E-Verify employer - all hired positions require successfully passing an E-Verify Check.  

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