Experienced Crew (Full time) - Beltline

Cluck N Cleaver; Calgary; On-site; CAD 180,000 - 280,000; Full time

Benefits offered by this job

Competitive compensation

Work-life balance

Tailored benefits

Career growth and support

Exclusive perks

Job summary

HUB International is seeking a Chief Sales Officer, Employee Benefits & Retirement Canada, to lead the national sales strategy and go-to-market effectiveness of the EB&R division. You will align with regional EB leaders, carrier partners, and the NAT team to drive growth and market leadership across Canada.

You will shape product and benefits innovation, partner with Marketing, and engage senior stakeholders to advance HUB’s competitive position in employee benefits and retirement markets.

Qualifications

• 15+ years of leadership experience in employee benefits, group insurance, or related field.
• Proven track record in senior strategy, innovation, or executive roles within brokerage, carrier, or benefits consulting.
• Deep knowledge of the Canadian employee benefits landscape and regulatory environment.

Responsibilities

• Define and execute a national sales strategy for EB&R Canada aligned to regional targets.
• Drive new business by equipping producers with differentiated value propositions and content.
• Establish and track commercial metrics: pipeline growth, new business conversion, product penetration.
• Collaborate with regional leaders and NAT team to identify growth opportunities across markets.
• Champion producer engagement and recruitment with a compelling value proposition.
• Represent HUB in industry forums, translate thought leadership into client content and market intelligence.

Skills

Sales leadership

Strategic planning

Executive presence

Canada market knowledge

Go-to-market

Vendor relationships

Product & innovation

Job description

HUB International’s National Employee Benefits and Retirement Team is dedicated to driving growth and excellence across Canada by supporting our regional teams. As strategic partners, this team collaborates with local offices to expand and enhance our Employee Benefits and Retirement divisions, ensuring we deliver best-in-class solutions for clients nationwide. Through innovative strategies, expert guidance, and a shared commitment to success, the National Team empowers our regions to meet evolving market demands, strengthen client relationships, and achieve sustainable growth in the benefits and retirement space.

About The Role

The Chief Sales Officer, Employee Benefits & Retirement (EB&R) Canada is a senior executive responsible for driving the national sales strategy and go-to-market effectiveness of HUB's EB&R division. This role sits at the intersection of sales leadership, product innovation, market positioning, and strategic partnership, serving as both a commercial driver and a market-facing voice for the division.

Reporting to the President, Employee Benefits, Retirement & Life, the CSO will work in close partnership with the National EB&R team, regional EB leaders, HUB Financial, and carrier and vendor partners. This is an influence-driven role as much as it is a direct leadership role, success depends on the ability to align and mobilize across a matrixed organization.

What You’ll Do

Sales Strategy & Revenue Growth

• Define and execute a national sales strategy for Employee Benefits and Retirement Canada, aligned to regional revenue targets and growth objectives.
• Drive new business development by equipping producers and advisors with differentiated value propositions, tools, and market-facing content.
• Establish and track key commercial metrics - pipeline growth, new business conversion, product penetration, and hold accountability for outcomes.
• Collaborate with regional EB leaders and the NAT team to identify and pursue growth opportunities across market segments and geographies.
• Champion producer engagement and recruitment by ensuring the division's value proposition is compelling and competitive in market.

Thought Leadership & Market Positioning

• Serve as HUB's senior voice on benefits innovation, representing the organization at industry forums, conferences, and with key market stakeholders.
• Monitor and synthesize emerging trends in employee benefits, healthcare, group insurance, and workforce policy to inform divisional strategy.
• Develop and communicate a compelling innovation narrative that reinforces HUB's market position and differentiates our value proposition.
• Partner with Marketing and Communications to translate thought leadership into client-facing content, white papers, and market intelligence.

Product & Benefits Innovation

• Lead the identification and prioritization of new benefits products, programs, and service offerings that address evolving client needs — bringing market insight, client intelligence, and a clear point of view on where the division should invest.
• Establish and govern an innovation pipeline — from ideation through piloting to scaled deployment — in partnership with practice leaders, operations, and product teams who own execution and delivery.
• Collaborate with cross-functional partners across the division to translate product concepts into market-ready offerings; influence and align without direct authority over delivery teams.
• Identify whitespace opportunities and unmet market demand by working closely with account management, client strategy, and regional EB leaders.
• Ensure innovation initiatives align with HUB's growth objectives, profitability targets, and risk appetite.
• Cultivate and manage senior-level relationships with insurance carriers, benefits administrators, and third-party vendors to secure preferred access, exclusive programs, and competitive arrangements.
• Negotiate and structure strategic partnerships that expand HUB's product shelf and create differentiated client value.
• Ensure alignment between carrier/vendor strategy and divisional priorities; proactively identify and address partnership gaps or emerging risks.
• Represent HUB in joint innovation initiatives with key carrier and vendor partners.

What You’ll Need for Success

• 15+ years of progressive leadership experience in employee benefits, group insurance, or a closely related field.
• Proven track record in a senior strategy, innovation, or executive role within a brokerage, carrier, or benefits consulting firm.
• Deep knowledge of the Canadian employee benefits landscape, including group insurance products, regulatory environment, and market dynamics.
• Demonstrated success building and managing carrier and vendor relationships at a senior level.
• Experience leading product development or go-to-market initiatives, from concept through commercialization.
• Strong command of benefits-related technology trends, digital platforms, and data analytics applications.
• Exceptional communication and executive presence; credible and compelling with both internal leadership and external audiences.
• Strategic thinker with the operational acumen to translate vision into actionable plans and measurable outcomes.
• Proven ability to lead through influence in a matrixed organization; able to align cross-functional stakeholders without direct authority.
• Experience driving sales strategy and commercial accountability at a divisional or national level.

What’s in it for you?

Your well-being is our priority, and we back this up with a wealth of benefits:

• Competitive Compensation: Benefit from a pay structure that includes incentives, bonuses, and opportunities to increase your earnings.
• Work-Life Balance: Enjoy flexible work arrangements and generous time off to support your personal and professional life.
• Tailored Benefits: Access a personalized benefits package, including company-matched RRSPs, designed to meet your unique needs.
• Career Growth and Support: Invest in your future with HUB! Take advantage of our sponsored training and development programs, tuition reimbursement opportunities, and coverage for professional license fees and membership dues—everything you need to support your growth and excel in your career.
• Exclusive Perks: Take advantage of discounts on events, travel, accommodations, and personal home & auto insurance.

At HUB, we believe that diversity drives innovation, equity fosters opportunity, and inclusion creates a culture where everyone thrives. We are committed to building a workplace that reflects the communities we serve and where every employee feels valued, respected, and empowered to bring their whole self to work. By embracing diverse perspectives and fostering an inclusive environment, we cultivate a collaborative and dynamic team that delivers exceptional results for our clients and communities.

Why Choose HUB?

When you choose HUB, you're choosing a competitive, exciting, and friendly work environment that strategically positions you for longevity and offers significant advancement, growth, and success opportunities. To read more about HUB, please visit -

About HUB International

Headquartered in Chicago, Illinois, is a leading full-service global insurance broker and financial services firm providing risk management, insurance, employee benefits, retirement and wealth management products and services. With more than 22,000 employees in offices located throughout North America, HUB’s vast network of specialists brings clarity to a changing world with tailored solutions and unrelenting advocacy, so clients are ready for tomorrow.

We’re not just an insurance broker, we’re a team of passionate professionals dedicated to innovation, excellence, and empowering our clients and communities through personalized support and expertise.

If you’re interested in learning how you can grow your career at HUB, visit our to explore our opportunities.

Department General ManagementRequired Experience: More than 15 years of relevant experienceRequired Travel: Up to 25%