ARE YOU INTERESTED IN JOINING AN INNOVATIVE LOGISTICS TECHNOLOGY COMPANY?

Loadsmart is a growth-stage technology company valued at over $1 billion (a true Tech Unicorn)!We are a collection of industry veterans and user-centered engineers using innovative technology to fearlessly reinvent the future of freight by helping shippers, brokers, warehouses and carriers to move more with less.
With headquarters in Chicago and a globally distributed remote team, Loadsmart continues to attract top talent committed to driving meaningful change. We seek professionals who embody our core values: curiosity, clarity, results, commitment, and teamwork.
We are seeking a highly experienced and strategic Senior Director of People Operations to lead our global HR function. Reporting directly to the Chief Financial Officer (CFO), this is a critical leadership role that will partner closely with the executive team to drive our people strategy, ensuring it directly supports our business objectives, particularly our journey towards profitable growth and operational efficiency. You’ll be instrumental in shaping our organizational culture, optimizing our talent, and providing expert guidance across all HR disciplines, with a strong emphasis on compensation.
Job Type: Exempt
DEPARTMENT: G&A - People and Experiences
LOCATION: Chicago

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.
  The compensation offered for this role will be based on multiple factors such as location, the role’s scope and complexity, the candidate’s experience and expertise. In addition to your base compensation offer, this role is eligible for an incentive bonus, stock options and benefits listed below.

• 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.