President

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 .

I nsureon   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

A ctual 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.

#SPG

Department Business Operations

Required Experience: More than 15 years of relevant experience

Required Travel: Up to 25%

Required Education: Bachelor's degree (4-year degree)

Equal Employment Opportunity: HUB International Limited is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, protected veteran status, or any other characteristic protected by applicable federal, state, or local law.

Reasonable Accommodations: HUB International Limited is committed to providing reasonable accommodations to qualified individuals with disabilities throughout the application and hiring process. If you need a reasonable accommodation to access our career site, complete an application, or participate in any part of the hiring process, please contact the Recruiting Team at [email protected]. This contact information is for accommodation requests only and should not be used to inquire about the status of an application.

E-Verify: HUB International Limited participates in E-Verify. Please refer to Our Recruiting Process | Applicant Notices: E-Verify Program for additional information.