Territory Sales Representative (Insurance)

Location: On-site at 401 N Michigan Ave, Ste 2400, Chicago, IL; up to 60% travel throughout the assigned Midwest territory is required.

Salary: $75,000–$100,000 base compensation per year.

Company

hirify.global is an insurance services company, with this role supporting Wholesure Inc., a division focused on independent agency partnerships.

What you will do

• Develop, maintain, and strengthen relationships with independent insurance agencies across the assigned Midwest territory.
• Conduct at least 15 in-person agency visits per week to identify opportunities and provide ongoing support.
• Recruit and appoint new agency partners and support their onboarding during the first 30 days.
• Collaborate with division directors, underwriters, brokers, and internal marketing to expand agency production and identify cross-selling opportunities.
• Represent Wholesure at conferences, trade shows, networking events, webinars, and training sessions.
• Track agency interactions, sales activity, pipeline progress, market intelligence, and territory performance in CRM systems.

Requirements

• Professional experience building, maintaining, and growing business relationships.
• Strong interpersonal, presentation, negotiation, communication, organizational, and time-management skills.
• Ability to analyze market trends, identify business-development opportunities, and independently manage a sales territory.
• Proficiency with Microsoft Office and CRM platforms.
• Valid driver's license and ability to travel independently throughout the assigned territory.
• Bachelor's degree in Business, Marketing, Insurance, or a related field preferred, or equivalent relevant experience; previous insurance sales, business development, agency management, or territory management experience is preferred.

Nice to have

• Active Property & Casualty insurance license, or the ability to obtain one within 60 days of employment.
• Interest in continuing education, professional development, and applicable insurance designations.

Culture & Benefits

• On-site collaboration with team leadership and cross-functional partners.
• Medical, dental, vision, life, and disability insurance.
• Paid time off, holidays, paid sick time, and employee assistance resources.
• 401(k) plan with immediate vesting, HSA, FSA, and commuter benefits.
• Paid maternity and paternity leave, including for adoptive parents, plus legal-plan and pet-insurance options.