About the Hiring Company

Our client is a growing, family-owned specialty insurance agency focused on providing commercial insurance and risk management solutions to businesses within a highly specialized industry. With operations across 38 states and plans for continued national expansion, the company has built a strong reputation through deep industry expertise, educational resources, and a consultative approach to insurance.

Rather than simply selling insurance policies, the company serves as a trusted advisor to business owners, providing risk management guidance, industry-specific expertise, educational content, and tailored insurance solutions. Their specialized market knowledge and strong industry relationships have helped establish them as a recognized name within their niche.

About the Role

We are seeking a Sales Agent to drive new business development within a specialized commercial insurance market. This is a hunter-focused, individual contributor role responsible for developing relationships with business owners, identifying opportunities, managing the full sales cycle, and building a portfolio of recurring commission-based business.

The ideal candidate is a self-motivated sales professional who thrives on prospecting, enjoys building relationships with business owners, and is motivated by the opportunity to build significant long-term, renewable income. This is not a transactional sales environment—the role involves consultative selling, longer sales cycles, and the opportunity to become a recognized expert within a specialized industry.

Key Responsibilities

• Prospect and develop new business opportunities within a defined multi-state territory.
• Build relationships with business owners, founders, presidents, and operators.
• Generate opportunities through proactive outbound prospecting, referrals, networking, industry events, and the company's existing prospect database.
• Manage the full sales cycle from initial prospecting and discovery through proposal, negotiation, and close.
• Conduct consultative conversations to understand clients' business operations, risks, and insurance needs.
• Develop a deep understanding of the target industry and become a trusted resource for prospective clients.
• Maintain consistent prospecting activity and build a healthy sales pipeline.
• Manage longer sales cycles, with opportunities potentially taking several months to 1–2 years to close.
• Attend approximately 4–5 industry conferences and trade shows annually to develop relationships and generate new business.
• Participate in regional and national industry events and occasional market visits.
• Build and manage a portfolio of accounts that generates recurring renewal commission income.
• Collaborate with a close-knit internal team while taking individual ownership of sales performance and results.
• Consistently work toward new account acquisition and revenue targets.
• Demonstrate strong CRM, pipeline management, follow-up, and sales activity discipline.

Qualifications

• Minimum of 3 years of sales experience, with 3–5 years being ideal.
• Proven experience in full-cycle sales and closing business.
• Demonstrated success in hunting for and acquiring new customers.
• Experience in commission-based, quota-carrying, or performance-driven sales environments strongly preferred.
• Strong business development and prospecting skills, with the ability to create opportunities independently.
• Experience selling to business owners, founders, presidents, or other senior decision-makers.
• Insurance sales experience is highly desirable.
• Experience within the landscaping, green industry, tree care, arborist, or related equipment industries is a strong advantage.
• Candidates from equipment manufacturers or dealers serving specialized commercial industries may also be considered.
• B2B sales experience preferred but not mandatory.
• Comfortable managing longer, consultative sales cycles rather than high-volume transactional sales.
• Highly self-motivated, competitive, resilient, and accountable.
• Coachable and receptive to feedback and ongoing development.
• Entrepreneurial mindset with a strong desire to build long-term earning potential.
• Comfortable with a compensation structure that increasingly rewards performance and commission production.
• Strong communication, relationship-building, and presentation skills.
• Willingness to travel approximately 4–5 times annually for conferences, trade shows, and occasional customer visits.
• Candidates located within approximately 45 minutes of the company's Milwaukee-area office are strongly preferred.
• Ability to work in a hybrid environment, including approximately 2–3 days per week in the office.

What We Offer

• Competitive base salary with a structured transition toward predominantly commission
• Attractive commission structure designed to reward long-term sales performance.
• 50% of new business commissions and 35% of renewal commissions.
• Opportunity to build substantial recurring commission income over time.
• Year 1 total earnings potential of approximately $70,000–$80,000.
• Year 2 earning potential of $100,000+.
• Year 3 target earnings of approximately $150,000+.
• Significant upside for high performers, with top producers currently earning approximately $180,000–$200,000+.
• Group health insurance with approximately 75% employer coverage for individual plans and 50% for family coverage.
• Simple IRA with a 3% employer match.
• Voluntary life insurance.
• Disability insurance.
• Hybrid work environment with a collaborative, close-knit team.
• Approximately 4–5 industry conferences and trade shows annually.
• Opportunity to become a recognized expert within a specialized and growing market.
• Long-term opportunity to build renewable income and significant earning potential.
• Opportunity to have a visible impact within a growing entrepreneurial organization with ambitious long-term growth plans.

About Us

At Peak Sales Recruiting, we specialize in connecting top B2B sales talent with businesses across North America. As a leading sales recruiting firm, we pride ourselves on understanding the unique needs of our clients and candidates. We would love to work with you to help you find your next exciting career opportunity and ensure the right match between your skills and the perfect role.

How to Apply

Ready to take your career to the next level? Apply now! Submit your resume and a brief cover letter outlining why you're the perfect fit for this role.

We look forward to hearing from you!

Job Code – 21455