President, Insureon 

HUB International – Specialty Program Group 

• Location: Chicago, IL

• Function: Executive Leadership

• Reports to the Head of HUB Small Business  

About Insureon 

Insureon, a HUB International and SPG company, is the largest digital insurance agency for small businesses (P&C only) in the United States.  

Insureon combines technology, a streamlined digital platform, a team of insurance professionals and deep carrier relationships to help small business owners find, compare, and purchase commercial insurance quickly and efficiently online. 

The business is at an inflection point — actively executing on a multi-year growth strategy with initiatives designed to accelerate profitable growth and expand its leadership position in the small business market. 

The Opportunity 

This is a unique opportunity to lead a category-defining business through a pivotal phase of growth and transformation. Insureon will continue to be a pillar of HUB’s broader Small Business strategy and will receive full support to execute on its roadmap.  

The role carries full P&L ownership and the authority to shape the team, the technology roadmap, and the go-to-market strategy.  

The President will also serve as a senior executive sponsor for HUB’s broader Small Business Insurance initiative — a comprehensive, enterprise-wide effort spanning operations, digital distribution, regional production, and strategic partnerships. 

Position Summary 

The President of Insureon is accountable for the full financial, strategic and operational performance of the business. This executive has direct oversight of Strategy, Customer Acquisition (including Paid Search, Organic, AI platforms, and emerging channels), Product, Technology, and Agency Operations (including Sales, Account Management, Service, and Compliance).  

Operational Oversight 

• Oversee five core functions: Strategy, Customer Acquisition, Product, Technology, and Agency Operations 

• Manage full P&L accountability and ensure operational excellence across all business units 

• Build and develop high-performing leadership teams capable of executing a complex, multi-workstream agenda 

• Drive cross-functional collaboration across HUB Small Business and Specialty Program Group 

• Partner with the Human Resources leader to drive talent acquisition, organizational development, employee engagement, and culture initiatives — including the creation and stewardship of a strong corporate culture across the business 

Growth & Digital Distribution 

• Accelerate digital customer acquisition and eCommerce capabilities to capture share in the small business insurance market 

• Develop and expand partnerships with carriers, technology platforms, and distribution intermediaries 

• Leverage market intelligence, data providers, and analytics to sharpen competitive positioning and product development 

• Serve as the company’s primary voice on small business insurance trends, digital innovation, and market evolution 

Financial Management 

• Develop and manage annual budgets, financial forecasts, and performance reporting in alignment with HUB International expectations 

• Monitor key financial and operational metrics, identifying risks and opportunities to ensure sustained business performance 

Strategic Planning 

• Lead annual and long-range strategic planning processes, setting priorities and allocating resources across the business 

• Identify and evaluate market opportunities, adjacencies, and strategic initiatives that drive Insureon’s competitive position 

• Align strategic plans with HUB International’s enterprise objectives and communicate progress to senior leadership 

IT Management (Internal & Vendor) 

• Oversee internal IT operations, ensuring systems, infrastructure, and tools support business performance and scalability 

• Manage vendor relationships and third-party technology partnerships, ensuring accountability, performance, and cost-effectiveness 

• Ensure data security, compliance, and technology governance standards are maintained across all internal and vendor-managed systems 

Carrier Relationships 

• Maintain and strengthen carrier relationships at an executive level, ensuring alignment on appetite, capacity, and strategic priorities that support Insureon’s small business insurance offerings 

Enterprise & Stakeholder Engagement 

• Represent Insureon at the executive level within HUB International, SPG and with key external stakeholders, including carrier partners and industry organizations 

• Contribute to industry thought leadership and, where appropriate, philanthropic and civic engagement on behalf of the company 

Qualifications Required 

• 15+ years of commercial insurance experience, with significant expertise in small business insurance 

• Demonstrated success leading complex, multi-functional organizations at scale through periods of transformation 

• Proven track record in digital distribution, eCommerce, or technology-enabled insurance models 

• Experience operating within a large, matrixed organization (broker, carrier, or specialty program environment) 

• Strong executive communication, stakeholder management, and P&L ownership experience 

Preferred 

• Experience at a top-tier commercial carrier or large national brokerage 

• Familiarity with API-based distribution platforms, insurtech models, or digital agency operations 

• Active involvement in industry organizations (e.g., IIABA, NAPSLO/TMPAA, IICF) 

• Bachelor’s degree required; advanced degree a plus 

• Industry designation preferred (e.g., CIC, CPCU, ARM) 

Compensation & Benefits 

HUB International offers a competitive total compensation package commensurate with experience. The total compensation range for this role is $425,00 - $550,00 annually, reflecting the seniority and scope of the position. 

Total compensation includes: 

• Annual performance bonus eligibility 

• 401(k) with company match 

• Comprehensive medical, dental, and vision benefits 

• Executive perquisites and professional development support 

• Paid time off and company holidays  

• Potential long-term incentive / equity participation 

Actual compensation will be determined based on the selected candidate’s qualifications, experience, and location. 

About HUB International 

HUB International is one of the world’s largest insurance brokerage and financial services firms, with more than 17,000 employees and offices across North America. HUB’s Specialty Program Group manages a portfolio of specialty and program businesses, including Insureon, serving niche markets with deep expertise and dedicated resources. 

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