Your Trusted Canadian Benefits Advisor

Group Benefits
Built for Your People

Expert, independent group benefits consulting for Canadian employers, from sole proprietors to large organizations. Plans designed to attract talent, retain your team, and keep costs in check.

Winnipeg skyline
15+
Years of Experience
Trusted Carrier Relationships
CA
Serving Clients Across Canada

Local Expertise.
Genuine Advocacy.

With over 15 years of experience, we bring independent, personalized benefits advice to Canadian employers of every size. We're not a call centre. We're a dedicated advisor who takes the time to understand your business.

Because we work independently, we can objectively recommend the plan that truly fits your organization, not the one that's easiest to sell.

"Our goal is simple: give every employer access to the same quality of benefits advice, regardless of size."

  • Independent & Unbiased We represent you, not the insurance carriers.
  • Nationally Licensed Advisors Fully licensed, regulated, and locally accountable.
  • Ongoing Plan Management We stay with you through renewals, claims, and changes.
  • Cost Control Strategies Smart plan design to maximize value and control premiums.

Comprehensive Group
Benefits Solutions

Everything you need to build, manage, and maintain a benefits plan that works for your team.

Plan Design & Implementation

Tailored plan design that balances employee needs with your budget, benchmarked against industry peers.

Health · Dental · Vision

Life & Disability Coverage

Group life, short and long-term disability, and critical illness coverage: protection your employees can count on.

Life · STD · LTD · CI

Renewal Management

We review your experience data at every renewal and benchmark your plan to make sure you're in the right coverage at the right price.

Annual Review · Market Comparison

Employee Assistance Programs

EAP and mental health resources integrated into your plan, supporting the whole person, not just the medical claim.

EAP · Mental Health · Wellness

HR & Administration Support

We provide the guidance and resources your HR team needs to manage enrolment, eligibility changes, and claims with confidence.

Enrolment · Claims · Comms

Executive & Owner Solutions

Specialized coverage for business owners and executives, including executive medical care, enhanced life and disability insurance, and ownership-level benefit strategies designed to protect what you've built.

Executive Medical · Key Person · Owner Options

The Pennycook
Difference

With a national broker, your account sits in a queue. With us, you have a dedicated advisor who knows your name, your plan, and your people: someone who picks up the phone.

01

Local Relationships

Committed to every client regardless of size. We take the time to understand your industry and your people.

02

Carrier Independence

No quotas, no preferred carriers. Just the right fit for your organization.

03

Proactive Service

We monitor your plan year-round and flag issues before they become costly problems.

04

Transparent Advice

Plain language, no jargon. You'll always know what you're buying and why.

Our Four-Step Process

01

Discovery Meeting

We learn about your organization, your people, and your goals. No assumptions. Just listening.

02

Market Review

We analyze your current coverage, benchmark against peers, and identify the best options available.

03

Plan Recommendation

A clear proposal with options laid out side by side, so you can make a confident, informed decision.

04

Ongoing Partnership

Annual reviews, claims support, and ongoing guidance. We stay engaged long after the plan is in place.

"Benefits consulting isn't transactional. The best outcomes happen when an advisor knows your business, your people, and your goals. The right plan doesn't just protect your employees today, it helps you attract the people you need to grow tomorrow."
Randall Pennycook — Randall Pennycook, Co-Founder

Let's Talk About
Your Team

Reviewing an existing plan, starting fresh, or just have questions? We'd love to connect. No obligation, no pressure.

Location Manitoba, Canada (Serving Clients Nationally)
Phone (204) 803-1575 | (204) 906-1160
Email info@pennycookbenefits.ca