Job Description: General Counsel

Location: St. Charles, MO

Reports to: Chief Executive Officer

About the Company

Milestone is a leader in the transportation leasing industry, known for delivering reliable, innovative, and cost-effective solutions that support our customers’ success. With a rapidly expanding footprint and a commitment to operational excellence, the company is poised for continued growth and strategic transformation.

Position Summary

The General Counsel will serve as the chief legal officer and a member of the executive leadership team, providing trusted counsel to the CEO, Board of Directors, and senior management. The successful candidate will be responsible for developing and executing the company’s legal strategy while overseeing day-to-day legal operations.

This role requires a strong commercial legal background with expertise in leasing contracts, real estate transactions, defaults, and repossessions, as well as broad experience in risk management, compliance, and corporate governance. The General Counsel will balance strategic vision with hands-on execution, ensuring legal rigor while enabling the business to move with speed and confidence.

Key Responsibilities

• Serve as a strategic partner to the CEO and Board, providing sound, pragmatic, and business-oriented legal guidance across all aspects of the organization.
• Lead and oversee the drafting, negotiation, and management of leasing agreements, real estate contracts, and equipment financing arrangements.
• Direct the company’s approach to customer defaults and repossessions, including drafting default notices, managing disputes, and ensuring compliance with the Uniform Commercial Code (UCC) and other applicable laws.
• Oversee all litigation, arbitration, and dispute resolution, ensuring effective management of outside counsel and favorable business outcomes.
• Guide corporate governance activities, including board matters, compliance programs, and corporate policies.
• Anticipate and manage regulatory, legal, and contractual risks across the enterprise, ensuring adherence to federal, state, and local laws affecting the transportation industry.
• Build and mentor a high-performing legal function, fostering a culture of integrity, accountability, and proactive risk management.
• Contribute as a thought leader in strategic business discussions, aligning legal priorities with company objectives.

Candidate Profile

Education & Credentials

• Juris Doctor (JD) from an ABA-accredited law school.
• Active membership in good standing with at least one U.S. state bar; ability to obtain in-house counsel registration where required.

Professional Experience

• 10–15 years of progressive legal experience, including at least 5 years in a senior in-house role or serving transportation, logistics, equipment leasing, or real estate clients.
• Proven track record of contract negotiation, leasing, defaults, and repossessions.
• Broad knowledge of corporate governance, regulatory compliance, and risk management.
• Demonstrated ability to advise boards and executive leadership teams with clarity, confidence, and authority.
• Experience managing litigation and external legal partners in a cost-effective, business-minded manner.

Leadership & Personal Attributes

• Strategic thinker with the ability to translate complex legal issues into actionable business solutions.
• Exceptional communication, negotiation, and relationship-building skills.
• High level of integrity, sound judgment, and professional maturity.
• Commercial mindset with the ability to balance legal rigor and business pragmatism.
• Demonstrated ability to thrive in a fast-paced, growth-oriented environment.

Compensation

An attractive and competitive executive compensation package will be offered, including base salary, performance-based incentives, comprehensive health and retirement benefits, and professional development support.

The Opportunity

This is a unique opportunity for a seasoned legal executive to join a dynamic, growth-focused transportation company as a key member of the leadership team. The General Counsel will have a visible, influential role in shaping the company’s future, ensuring that growth is supported by sound legal frameworks, strong governance, and effective risk management.