Vice-President – People & Talent

Vice-President – People & Talent

Companies: Windley Ely (Claims Management) & Halpenny Group (P&C Insurance Broker & Group 

Benefits)

Location: London| Ottawa | Toronto 

Reports To: Executive Leadership

Employment Type: Full-Time, Permanent

Bilingualism: French/English an asset

Compensation: Competitive Base + Performance Incentive ($110K – $140K)

About the Organizations

Windley Ely is a national claims management company headquartered in London, ON, with branch offices in Calgary, Vancouver, Montreal, and Ottawa (155 employees). Halpenny Group is an independent commercial P&C insurance broker and group benefits provider operating in Ottawa and Toronto (50 employees). Together, these organizations employ approximately 205 professionals across six offices and four provinces. This role provides shared HR leadership across both companies under common ownership.

The Opportunity

Reporting to executive leadership, the Vice-President – People & Talent will serve as the strategic and operational HR partner for both organizations. This is a hands-on, high-impact role requiring equal parts people strategy and day-to-day HR delivery — from attracting specialized insurance talent to navigating multi-provincial compliance across two distinct businesses.

Key Responsibilities

• Develop and execute a unified people strategy for both organizations; advise leadership on organizational design, workforce planning, and succession

• Lead talent acquisition for Windley Ely (functional claims staff and geographic branch support) and Halpenny Group (senior commercial brokers, account executives, and group benefits specialists)

• Manage full-cycle employee relations across ON, AB, BC, and QC — grievances, performance management, accommodation, and terminations in compliance with applicable provincial ESA and Human Rights legislation

• Benchmark and administer compensation for claims management and brokerage roles; manage group benefits plans; support commission and production incentive structures

• Ensure compliance with provincial employment standards, AODA, PIPEDA, and RIBO licensing requirements across all jurisdictions

• Coordinate licensing and professional development: RIBO CE, CIP, FCIP, CAIB, CPIB, GBA/CEBS for Halpenny; WCB/WSIB adjudication training and CDMS pathways for Windley Ely

• Manage HRIS, multi-provincial payroll coordination, and workforce reporting across a combined ~205-person, six-office operation

Qualifications

Required:

• 8–10+ years of progressive HR experience, with a minimum of 3–5 years in a senior or director-level role

• Demonstrated experience in the Canadian insurance industry — brokerage, claims management, or a closely related sector

• Solid working knowledge of employment standards across multiple Canadian provinces, particularly Ontario

• Proven ability to manage HR independently across geographically distributed, multi-entity teams

• CHRL designation

Strong Assets:

• Familiarity with RIBO licensing, commercial P&C lines, WCB/WSIB claims environments, or group benefits administration

• Knowledge of industry designations: CIP, FCIP, CAIB, CPIB, GBA, CEBS, CDMS

• Multi-jurisdictional HR experience across ON, AB, BC, and QC

• Functional bilingualism in French and English

What We Offer

Windley Ely and Halpenny Group offer a competitive total rewards package including:

• Competitive base salary commensurate with experience

• Comprehensive group benefits plan including health, dental, wellness savings account, and Group RRSP

• Professional development support and designation sponsorship (CIP, FCIP, CAIB, CPIB, CHRL)

• Hybrid work flexibility

• Direct access to ownership and executive leadership

• A unique opportunity to shape HR across two growing Canadian risk management businesses

How to Apply

Qualified candidates are invited to submit a resume and cover letter in confidence to careers@halpenny.com with the subject line: Vice-President – People & Talent”. We thank all applicants for their interest; however, only those selected for an interview will be contacted. Windley Ely and Halpenny Group are committed to equity, diversity, and inclusion in the workplace. Accommodations are available on request throughout the selection process.