Senior Director, People Operations

WHAT YOU GET TO DO:

• Act as a trusted advisor to the CFO and executive leadership team, developing and executing HR strategies that align with and advance the company’s overall business goals, with a particular focus on supporting growth, profitability, and cost efficiency from a people perspective.
• Develop and implement strategies for talent management, performance management, and employee development that optimize talent investment while fostering growth.
• Serve as the primary subject matter expert and thought leader for all compensation matters, including base pay, incentive plan design, and long-term incentives — to attract, retain, and motivate top talent while maintaining cost-effectiveness and internal equity.
• Partner with leadership to develop innovative incentive plans that drive desired business outcomes and support our profitability goals.
• Drive culture and engagement across all employees, especially considering the unique dynamics of our in-person brokerage team in Chicago, our Brazil-based engineering team, and a significant remote workforce.
• Oversee the effective administration of all benefits programs.
• Design and clearly communicate career paths and growth opportunities for employees.
• Champion a culture of continuous learning and development.
• Lead initiatives related to organizational design, workforce planning, and change management to enhance efficiency and productivity.
• Ensure HR policies and practices comply with global regulations and support a positive, productive work environment.
• Lead, mentor, and develop a high-performing HR team.

REQUIRED QUALIFICATIONS:

• 10+ years of HR experience, with at least 3-5 years in a senior HR leadership role (Senior Director HR, Head of HR, or similar), preferably within a tech or freight tech environment.
• Demonstrated deep expertise in compensation, including a proven track record of designing and implementing innovative compensation structures, incentive plans, and total rewards strategies. Experience with global compensation practices is a significant plus.
• Strong business acumen and financial literacy, with a clear understanding of how HR initiatives impact financial performance and profitability. 
• Experience operating in an environment focused on cost optimization and driving efficiency.
• Proven ability to develop and implement pragmatic HR solutions that address both strategic objectives and operational realities.
• Exceptional leadership and team management skills, with experience leading and developing global HR teams.
• Excellent communication, interpersonal, and influencing skills, with the ability to build strong relationships across all levels of the organization.
• Experience working in a fast-paced, growth-oriented startup environment, dynamic settings where adaptability and hands-on problem-solving are essential.
• Bachelor's degree in Human Resources, Business Administration, or a related field. Master's degree or relevant HR certifications (e.g., SPHR, SHRM-SCP, CCP) preferred.