THE COMPANY

This organization is a highly respected, long-standing leader in the corporate compliance and legal services sector. For more than four decades, it has supported law firms, financial institutions, and corporate legal teams with mission-critical services such as entity management, UCC filings, lien searches, due diligence support, and a wide range of regulatory and transactional compliance solutions.

Collaboration is strong across sales, customer service, operations, and leadership, creating a well-supported environment for client success. This is a place where top producers thrive, find long-term stability, and often build entire careers.

THE JOB

The Sales Representative will manage and grow a well-established, high-volume territory based in Chicago, with additional coverage across Wisconsin, Iowa, and Minnesota. This is a hybrid role combining in-office collaboration, field-based selling, and face-to-face meetings with law firms that rely on the company’s services for their own clients’ transactional, financial, and regulatory needs.

The person in this role will focus heavily on relationship-driven field sales, conducting client meetings face-to-face, driving revenue growth, and entertaining clients. The territory already has strong existing revenue and has been one of the company’s top-producing regions for multiple years, yet still offers substantial opportunity for growth through new business development. This is very much a hunter-oriented role—ideal for someone who can build deep relationships, open new doors, and create long-term value within the legal ecosystem.

THE QUALIFICATIONS

• 5–10 years of successful B2B sales experience
• Experience selling into the legal vertical or to law firms
• Proven ability to prospect and develop new business while managing a book of existing accounts
• Comfortable with face-to-face meetings, client entertainment, and relationship-based selling
• Ability to manage both fast transactional sales and longer consultative cycles
• Strong presentation, communication, and territory management skills
• Competitive, self-directed, and capable of managing a high-volume territory
• Ability to travel approximately 15% across a multi-state territory (Chicago, WI, IA, and MN)

THE BENEFITS

• Base salary ranges between $70,000–$85,000
• On-target earnings between $160,000–$180,000, with no cap on commissions
• 401k with match
• Medical, Dental & Vision insurance
• Established, high-performing territory with commission eligibility from day one
• Comprehensive training, including a structured 90-day onboarding program and ongoing development
• Strong internal support from sales leadership, customer service, and operations
• Hybrid work structure based out of the downtown Chicago office
• Long-term career stability in an organization with exceptional employee tenure