President

Sep 24, 2026

$425,000 - $550,000/year

President,Insureon

HUB International – Specialty Program Group

Location: Chicago, IL

Reports totheHead of HUB Small Business

AboutInsureon

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

Insureoncombinestechnology, a streamlined digital platform,a team of insurance professionalsand deepcarrierrelationships to help small business owners find, compare, andpurchasecommercial insurance quickly and efficientlyonline.

The business is at an inflection point — activelyexecutingonamulti-yeargrowth strategy with initiatives designed toaccelerateprofitable growthand expand its leadership position in the small business market.

The Opportunity

This is auniqueopportunity to lead a category-defining business through a pivotal phase of growth and transformation.Insureonwill 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 technologyroadmap, and the go-to-market strategy.

The President will also serveas asenior 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 ofInsureonis accountable for the fullfinancial,strategicand operationalperformanceof the business. This executivehasdirect oversightofStrategy, 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 HUBSmall Business andSpecialty 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

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

Monitor key financial and operational metrics,identifyingrisks and opportunities to ensure sustained business performance

Strategic Planning

Lead annual and long-range strategic planning processes, setting priorities andallocatingresources across the business

Identifyand evaluate market opportunities, adjacencies, and strategic initiatives that driveInsureon’scompetitive position

Align strategic plans with HUB International’s enterpriseobjectivesand communicate progress to senior leadership

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 aremaintainedacross all internal and vendor-managed systems

• Maintain and strengthen carrier relationships at an executive level, ensuring alignment on appetite, capacity, and strategic priorities that supportInsureon’ssmall business insurance offerings

Enterprise & Stakeholder Engagement

RepresentInsureonat the executive level within HUB International, SPGand with key external stakeholders, including carrier partners and industry organizations

Contribute to industry thought leadership and, whereappropriate,philanthropicand civic engagement on behalf of the company

Qualifications Required

15+ years of commercial insurance experience, with significantexpertisein small business insurance

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

Proventrack recordin digital distribution, eCommerce, or technology-enabled insurance models

Experienceoperatingwithin 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,insurtechmodels, or digital agency operations

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

Bachelor’s degreerequired;advanced degree a plus

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

HUB International offers a competitive total compensation packagecommensuratewith experience. Thetotal compensationrange for this role is $425,00 - $550,00annually, reflecting the seniority and scope of the position.

Total compensation includes:

Annual performance bonus eligibility

401(k) with company match

Executive perquisites and professional development support

Paid time off and company holidays

Potential long-term incentive / equity participation

Actual compensation will bedeterminedbased 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 than17,000 employeesand offices across North America. HUB’s Specialty Program Group manages a portfolio of specialty and program businesses, includingInsureon, serving niche markets with deepexpertiseand 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 This contact information is for accommodation requests only and should not be used to inquire about the status of an application.

HUB International is a premier global insurance broker offering tailored risk, insurance, employee benefits, and wealth management solutions to empower businesses and individuals.

Private Equity - T. Rowe Price, Temasek Holdings, Alpha Wave Global $1.6B

May 2025

Private Equity - Leonard Green & Partners

Sep 2023

Private Equity - Leonard Green & Partners

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Footprint

Where they work

Headquarters Chicago, IL

300 North LaSalle, 17th Floor, Chicago, IL 60654, US 783 Old Hickory Blvd, Brentwood, TN 37027, US 1330 Lady St, Columbia, SC 29201, US 3700 Steeles Ave W, Vaughan, ON L4L 8M9, CA 210 6th Ave, Pittsburgh, PA 15222, US 3510 N Causeway Blvd, Metairie, LA 70002, US 3636 American River Dr, Sacramento, CA 95864, US 625 Kenmoor Ave SE, Grand Rapids, MI 49546, US 3390 University Ave, Riverside, CA 92501, US 6701 Center Dr W, Los Angeles, CA 90045, US 600 Cleveland St, Clearwater, FL 33755, US 2000 S Colorado Blvd, Tower 2, Suite 150, Denver, Colorado 80222, US 2265 Upper Middle Rd E, Oakville, ON L6H 0G5, CA