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Added 6 days ago
Construction Litigation Lawyer (Associate)
ZSA Canada
Toronto, ON
Full-time
Our boutique law firm client is looking for a construction litigator to join its team in Toronto. The ideal candidate will have at least three years' experience working on a variety of…
Added 15 days ago
Associate Lawyer – Construction Litigation
Gowling WLG
Kitchener, ON
Full-time
Gowling WLG’s Kitchener office is currently seeking a motivated Associate Lawyer with 2-6 years of construction litigation experience to join the Construction Litigation practice group. The…
Added 18 days ago
Construction Litigation Lawyer (Associate)
ZSA Canada
Cambridge, ON · Greater Kitchener-Cambridge-Waterloo Metropolitan Area
Full-time
Our law firm client is looking for a construction litigator to join its team in its Kitchener-Waterloo office. The ideal candidate will have at least two years' experience working on a…
Added 18 days ago
Associate Lawyer – Construction Litigation
Gowling WLG
Kitchener, ON
Gowling WLG’s Kitchener office is currently seeking a motivated Associate Lawyer with 2-6 years of construction litigation experience to join the Construction Litigation practice group. The…
Added 17 days ago
Senior Legal Researcher, Expert Witness Advisory Services
Ridge and Partners LLP
London, ON · Bristol-London, ON
Full-time
You will be a Paralegal or Solicitor with experience in construction law, confident working with expert witnesses and familiar with standard building contracts. You may already be working…
Added 19 days ago
Senior Litigation Associate (5 - 9 Years’ Call)
DWF
Calgary, AB
Full-time
This position is ideal for a lawyer looking to take the next step in their litigation career. You will handle your own files and work directly with experienced counsel. You will receive…
Added 4 months ago
Corporate Lawyer
Groupe AGF / AGF Group
Longueuil, Quebec
…of innovation, we take pride in being the heartbeat of major construction projects in Canada and across the…
Added 3 months ago
Legal Counsel
Canadian Natural
Calgary, Alberta
Full-time
Canadian Natural is seeking an experienced oil and gas commercial lawyer to join its dynamic and collaborative team. Reporting to the Manager, Legal - Commercial Operations, the Legal…
Added 15 hours ago
Litigation Associate
Miller Thomson LLP
Saskatoon, SK
Full-time
Our Litigation Group is seeking an energetic, team-oriented, and entrepreneurial Lawyer to join the team in either of our Saskatchewan offices.
Added 2 days ago
Administrative Assistant - Disputes - Commercial & Construction Group
Borden Ladner Gervais LLP (BLG)
Vancouver, BC
Full-time
Manage Lawyer, Law Clerk and Practice Assistant enquiries in a prompt and efficient manner
Added 2 days ago
Associate - Corporate Commercial
Impact Recruitment
AB · Alberta, Canada
Full-time
This is an outstanding opportunity for an ambitious lawyer looking to take the next step in their career while gaining exposure to sophisticated commercial transactions and high-profile…
Added 2 days ago
Litigation Associate
Impact Recruitment
AB · Alberta, Canada
Full-time
The firm is seeking a lawyer with experience in one or more areas of litigation, including commercial, construction, environmental, employment, regulatory, estate, Indigenous, franchise, or…
Added 4 days ago
Intermediate to Senior Wills and Estates Lawyer
WBA Law LLP
Calgary, AB
Full-time
…include business law, litigation, banking and finance, tax law, construction law, employment law, wills and estates and real estate. Our lawyers come from diverse backgrounds and bring a…
Added 4 days ago
Complex Claims & Coverage Director
Weekday AI
Remote, Canada
Contract · Remote
Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional
Added 5 days ago
Project Legal (Development) – Legal Counsel/Senior Legal Counsel
Infrastructure Ontario
Toronto, ON
Full-time
Be the lead lawyer working on several projects simultaneously which are at different stages of a project lifecycle.
Added 5 days ago
Project Legal (Development) – Legal Counsel/Senior Legal Counsel
Infrastructure Ontario
Toronto, ON
Be the lead lawyer working on several projects simultaneously which are at different stages of a project lifecycle.
Added 5 days ago
Associate Lawyer - Commercial Litigation
Urban Legal Recruitment Inc.
Calgary, AB
Full-time
3-6 years of commercial litigation experience at a recognized Canadian law firm, particularly in complex commercial litigation, construction disputes, energy-related matters, and arbitration
Added 5 days ago
Litigation Associate
Miller Thomson LLP
Saskatoon, SK
Full-time
Our Litigation Group is seeking an energetic, team-oriented, and entrepreneurial Lawyer to join the team in either of our Saskatchewan offices.
Added 5 days ago
Legal Counsel
Mount Royal University
Calgary, AB
Full-time
This highly complex role requires a professional, technically proficient lawyer with deep institutional knowledge to deliver strategic, practical guidance to senior and executive university…
Added 14 days ago
Senior Lawyer
Reynolds Mirth Richards & Farmer LLP
Edmonton, AB
Contract
Our firm is seeking an experienced Labour, Employment and Occupational Health & Safety Lawyer to join our growing practice. We are a well-established, mid-sized Edmonton law firm recognized…
Added 15 days ago
Avocat(e), Droit corporatif et commercial (1-3 ans) / Lawyer, Corporate and Commercial Law (1-3 years)
Prelia Canada
Ottawa, ON
Full-time
…notamment la santé, les sciences, la fabrication industrielle, la construction, les technologies, les services financiers, l’immobilier commercial et les entreprises en…
Added 16 days ago
Lawyer & Patent Agent
BCF
Montreal, QC
Full-time
…serez au cœur de notre réussite et jouerez un rôle clé dans la construction de notre…
Added 16 days ago
Construction Litigation Associate
Life After Law
Toronto, ON
Full-time
This is an excellent opportunity for a litigation lawyer with 3–5 years of experience who is looking to further develop their practice at a highly regarded firm while working on…
Added 18 days ago
Project Finance / P3 & Infrastructure Lawyer
BJRC Recruiting
Toronto, ON
Full-time
The lawyer will advise clients throughout the lifecycle of major projects, including project development, financing, refinancing and strategic transactions. The practice involves…
Added 18 days ago
Mid-Level to Senior Associate, Insurance Litigation (Property Claims)
DWF
Vancouver, BC
Full-time
…join our Vancouver office. This opportunity is ideal for a lawyer with experience handling property-related claims on behalf of private insurers. We are looking for a lawyer who enjoys…

Weekday AI

Complex Claims & Coverage Director

Remote, Canada

Pay: Compensation: $80 per hour
Job type: Contract
Workplace: Remote
Experience: Have 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims
Working hours: 20 hours per week
Posting language: English
Posted: Sep 16, 2026

Apply About employer

Applications open in a new tab.

Original job description

This role is for one of our clients

Compensation: $80 per hour

We are partnering with a leading AI lab to train frontier models on high-quality insurance reasoning data. We're hiring Complex Claims and Coverage Directors to design high-severity and coverage-sensitive claim scenarios, evaluate model outputs against established senior claims standards, and help shape how the next generation of AI reasons about disputed coverage, litigation strategy, allocation, and major-loss resolution.

We welcome senior carrier claims professionals, complex-claims leaders, coverage specialists, and technical claim directors. This is an insurance-practitioner role and does not require a law degree or license to practice law.

What You'll Do

Design realistic scenarios involving disputed coverage, reservations of rights, excess exposure, multiple insureds, multiple carriers, allocation, litigation, mediation, bad-faith risk, and high-severity settlement strategy
Create work products such as complex claim strategies, coverage-position analyses, authority requests, litigation-management plans, reserve rationales, and escalation recommendations
Write "golden" reference responses at senior technical claims quality
Grade AI-generated responses against structured rubrics for policy analysis, strategic judgment, factual support, stakeholder awareness, and escalation discipline
Identify claim-handling positions that are internally inconsistent, unsupported by the record, operationally unrealistic, or outside the authority of a non-lawyer claims professional
Provide written feedback the research team uses to improve model behavior
Participate in onboarding office hours and calibration sessions

You're a Good Fit If You

Have 2+ years of professional experience handling complex, litigated, high-severity, or coverage-sensitive insurance claims
Have evaluated coverage issues and developed claim strategies involving multiple parties, layers, policies, or jurisdictions
Understand insurer duties, reservation-of-rights practices, litigation management, settlement authority, and escalation to internal or external counsel
Can distinguish an operational coverage position from formal legal advice and recognize when specialized legal review is required
Demonstrate exceptional written reasoning, defensible judgment, and high attention to detail
Are comfortable reviewing incomplete records and clearly separating facts, assumptions, open issues, and recommended next steps

Bonus Qualifications

CPCU, AIC, SCLA, ARM, or comparable insurance designation
Experience with excess casualty, professional liability, directors and officers, cyber, environmental, construction-defect, or other complex lines
Experience managing mediations, trials, coverage disputes, or extra-contractual exposure
Home-office technical claims or claim-governance experience
Experience overseeing TPAs, independent adjusters, experts, or panel counsel

Role Highlights

Minimum 20 hours per week (ideally 40+)
Role starts immediately, applications reviewed on a rolling basis

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

Apply About employer

More about this job

Responsibilities

Design complex insurance claim scenarios and evaluate AI model outputs against senior technical standards. Provide expert feedback to improve AI reasoning regarding coverage, litigation strategy, and major-loss resolution.

Requirements

Requires at least 2 years of professional experience handling complex, litigated, or coverage-sensitive insurance claims. Candidates must demonstrate exceptional written reasoning and the ability to distinguish operational coverage positions from legal advice.

Skills

Claims handling
Coverage analysis
Litigation management
Settlement strategy
Policy analysis
Risk assessment
Technical writing
Strategic judgment
Dispute resolution
Insurance reasoning
High-severity claims
Reservation of rights
Allocation
Bad-faith risk management
Data evaluation

Remote locations

Canada

Remote locations (standardized)

Canada

Visa sponsorship

Not detected in the job text

Keywords

Complex Claims
Coverage Director
AI Training
Frontier Models
Insurance Reasoning
Litigation Strategy
High-severity Settlement
CPCU
AIC
SCLA
ARM
Excess Casualty
Professional Liability
Directors and Officers
Cyber Insurance
Environmental Insurance
Construction Defect
TPA
Independent Adjusters
Panel Counsel
Reservation of Rights
Bad-faith Risk
Mediation
Policy Analysis
Claim Governance

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