Senior Group Benefits Underwriter

Oak House Benefits | Brantford, Ontario | Hybrid

Oak House Benefits is growing, and we're looking for an experienced Senior Group Perks Underwriter to join our team in a role created to support our continued growth.

We're looking for someone who truly knows group benefits underwriting - someone who has spent their career analyzing experience, building renewals, assessing risk and understanding what drives benefit costs.

But we're also looking for more than a great technical underwriter.

This is an opportunity to take that expertise beyond the numbers and have a greater influence on client strategy. You'll work alongside experienced Benefits Consultants, participate in renewal negotiation strategy, challenge insurer assumptions, identify opportunities and help translate complex financial information into advice our clients can understand and act on.

If you've built your career with an insurance company, benefits consulting firm or benefits brokerage and are interested in seeing the business from the OHB perspective, we'd love to talk.

What You'll Do

As a senior member of our Benefits team, you'll provide underwriting and financial expertise across a diverse portfolio of Canadian group benefit clients.

You'll

- Lead financial analysis and underwriting of group benefit plans, including insured, experience-rated and ASO arrangements.
- Analyze claims experience and understand the drivers behind Health, Dental, Life and Disability results.
- Review insurer renewal calculations and assumptions, including credibility, trend, pooling, reserves, large claims and retention expenses.
- Develop independent renewal projections and financial recommendations.
- Work alongside our Consultants to develop renewal negotiation strategies and challenge insurer positions when the data supports it.
- Analyze insurer marketing and RFP results and provide transparent financial comparisons and recommendations.
- Model plan design alternatives, cost-sharing arrangements and funding strategies.
- Identify emerging trends, risks and cost-management opportunities within client benefit programs.
- Prepare clear,



accurate and meaningful financial reporting for quarterly and annual client reviews.
- Participate in client meetings where your technical expertise and perspective can add value.
- Develop strong relationships with underwriting and account management teams across Canada's major insurers.
- Help us continue to improve our underwriting tools, reporting, processes and best practices.
- Share your expertise and provide technical guidance to other members of the Oak House team.

What We're Looking For: Direct Canadian group benefits underwriting experience is required for this position.

Our ideal candidate has developed their expertise within a Canadian insurance company, employee benefits consulting firm or benefits brokerage and brings a strong understanding of how group benefit plans are priced, funded and managed.

Ideally, you'll bring:

- 7+ years of progressive Canadian group benefits underwriting or closely related financial consulting experience.
- Strong technical knowledge of Health, Dental, Life and Disability benefits.
- Demonstrated experience underwriting and analyzing group benefit renewals.
- Strong knowledge of experience rating, credibility, trend, pooling, reserves, retention expenses and ASO arrangements.
- Experience analyzing insurer proposals and negotiating or supporting the negotiation of renewals.
- Advanced Excel and financial modelling skills.
- Exceptional analytical skills and attention to detail.
- The ability to look beyond the calculations and identify the story behind the numbers.
- Strong communication skills and the ability to explain complex underwriting concepts in practical, understandable terms.
- Confidence working with senior Consultants, insurers and clients.




- The ability to manage multiple priorities and deadlines while maintaining a high standard of accuracy.
- CEBS or another relevant industry designation would be an asset.

What Makes This Opportunity Different If you're currently working for an insurance company, you may be wondering what life on the consulting side looks like.

At Oak

House, you'll still get to do the technical work you enjoy - but you'll have the opportunity to see what happens next. You'll help determine the strategy. You'll work with multiple insurers and funding arrangements. You'll participate in negotiations. You'll see how your analysis influences plan design and client decisions. You'll help us win and retain clients. And you'll work directly with experienced consultants who value strong underwriting as an important part of great advice.

We aren't looking for someone to simply produce spreadsheets.

We're looking for someone who will ask questions, challenge assumptions and help us make better decisions for our clients.

Total Rewards

Salary Range of $75,000 CDN-$95,000 CDN

Company bonus plan, generous vacation, and of course, we have a great perks and retirement plan!

Learning & development support

About Oak House Benefits

Oak House Benefits is an independent Canadian benefits, retirement and absence & disability consulting firm. We built Oak House around a simple idea: people before profit.

Our team is made up of experienced industry professionals who believe clients deserve proactive advice, transparency and a consulting partner who genuinely feels like an extension of their team.

We're growing, but we're intentionally building Oak House one great person at a time.

That means we're looking for people who are excellent at what they do, care about the quality of their work, enjoy collaborating with other experienced professionals and want to make a meaningful contribution to the clients and colleagues around them.

If that sounds like you, we'd like to hear from you.

- Interested? Apply directly or reach out to us for a confidential conversation.

📌 Senior Group Benefits Underwriter (Brantford)
🏢 Oak House Benefits
📍 Brantford