Manager Benefits & Retirement Programs

Dexterra; Mississauga; On-site; CAD 90,000 - 120,000; Full time

Job summary

A leading North American company in Mississauga seeks a Manager, Benefits & Retirement Programs. The role involves leading the design, governance, and administration of benefits across Canada and the U.S. Candidates should have over 7 years of experience in benefits programs and excellent communication skills. The company promotes a flexible hybrid work environment and values diversity and inclusion.

Benefits

Flexible hybrid work model

Award winning safety culture

Supportive team environment

Qualifications

• 7+ years of experience in benefits and retirement programs (Canada & U.S.).
• 2+ years in a leadership role.
• Strong knowledge of unionized environments.

Responsibilities

• Lead the development and execution of benefits programs.
• Manage day-to-day administration of benefit schemes.
• Ensure compliance with ERISA, ACA, HIPAA, and other regulations.

Skills

Strategic thinking

Employee experience design

Analytical skills

Communication

Education

Post-secondary degree in HR or Business

Tools

HRIS systems (Dayforce preferred)

Excel

PowerPoint

Job description

Overview

Dexterra Group is a fast-growing, financially strong, publicly listed company (TSX:DXT). We have a far-reaching presence across the entire continent North America with hundreds of full-time and part-time opportunities at any given time. We aim to provide our people with more than just a job – we offer fulfilling opportunities in a culture that promotes stability, diversity and inclusion, camaraderie, employee recognition, work-life balance, and doing what you love. For over 75 years, the companies that began independently, and now form Dexterra Group, have been dedicated to serving North American clients to create and manage built environments that play a vital role in our economy and our local communities.

That’s something we’re truly proud of, Work That Matters, People Who Care.

Job Description

What’s the Role?

Are you a strategic thinker with a passion for delivering exceptional employee experiences through well-designed benefits and retirement programs?

We’re looking for a Manager, Benefits & Retirement Programs to lead the design, governance, and administration of our North American benefits portfolio - covering both union and non-union populations across Canada and the U.S.

What You’ll Be Doing

Strategic Planning & Governance

• Lead the development and execution of benefits and retirement programs aligned with our Total Rewards strategy and long-term business goals.
• Advise senior HR leaders on trends, cost containment, and risk management.
• Ensure compliance with internal audit, legal, and external reporting standards.
• Drive due diligence and integration for M&A activities.
• Support ESG and Total Rewards disclosures.

Program Design & Management

• Oversee health, dental, vision, life, disability, retirement, and wellness programs.
• Ensure programs are competitive, sustainable, and cost-effective.
• Provide expert support for collective bargaining and union negotiations.
• Benchmark offerings and recommend enhancements.

Operational Leadership

• Manage day-to-day administration including eligibility, enrollment, leaves, and retirement.
• Lead vendor relationships and performance reviews.
• Collaborate with Payroll, Finance, and HRIS for seamless data integration.
• Drive process improvements and automation.

Compliance & Risk Management

• Ensure full compliance with ERISA, ACA, HIPAA, COBRA, FMLA, and Canadian federal/provincial legislation.
• Maintain accurate documentation and lead internal/external audits.

Employee Engagement & Communication

• Develop clear, engaging communication strategies for benefits education.
• Lead open enrollment and change management campaigns.
• Collaborate with wellness committees to enhance employee well-being.

Team & Stakeholder Leadership

• Mentor a Total Rewards Specialist and influence cross-functional HR teams.
• Serve as a trusted advisor to leaders across North America.

Qualifications

Who are we looking for?

• Post-secondary degree in HR, Business, or related field.
• 7+ years of progressive experience in benefits and retirement programs (Canada & U.S.), including 2+ years in a leadership role.
• Strong knowledge of unionized environments and experience interpreting collective agreements.
• Familiarity with governance, audit, and reporting requirements for publicly traded companies.
• Proficiency in HRIS systems (Dayforce preferred); advanced skills in Excel, PowerPoint, and Word.
• Designations: CEBS (preferred); CHRP or CCP designations (assets).
• Proven success in developing and implementing Total Rewards strategies.
• Results-driven with a hands-on approach to execution.
• Strong analytical, critical thinking, and business acumen.
• Effective communicator with the ability to influence and build relationships across all levels.
• Experience leading teams and coaching for performance.
• Comfortable with change and skilled at leading others through transformation.
• Technically savvy and passionate about process improvement and automation.

Additional Information

WHAT’S IN IT FOR YOU?

• Be part of an industry that's more important than ever!
• Award winning safety culture.
• A flexible hybrid work model.
• Supportive team environment with room to grow together.
• Employee Referral Program.
• We are growing!

Dexterra Group is an equal opportunity employer committed to diversity and inclusion. We are pleased to consider all qualified applicants for employment without regard to race, colour, religion, sex, sexual orientation, gender identity, national origin, age, disability, protected veterans’ status, Indigenous status, or any other legally protected factors. Accommodation is available upon request at all stages of the selection process.

We thank all applicants for their interest and will contact those candidates selected for interview.

Please Note: We kindly ask that staffing or recruitment agencies do not contact us regarding this opportunity. We are not accepting agency referrals at this time.

#IND3