Senior Director, People Operations

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

• 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.

• 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.

WORKING AT LOADSMART:

• Competitive base salaries - we believe in rewarding top talent 

• Extremely competitive Equity package - become a shareholder in our company!

• Loadie Time Off - PTO and sick days without a limit

• Comprehensive Medical, Dental, and Vision insurance plans

• 401k Match 

We use AI-powered tools to assist with initial application reviews as part of our hiring process. All evaluations are subject to human oversight, and your information is handled in accordance with applicable data privacy laws.

At Loadsmart, we believe our biggest asset is our people. We are proud to be an equal opportunity employer, hiring and developing individuals from diverse backgrounds and experiences to add to our collaborative culture. Loadsmart treats all candidates and employees with respect and does not discriminate in our recruiting, hiring, and promoting processes, including on the basis of race, color, religion, sex, age, sexual orientation, gender identity and/or expression, national origin, veteran status, or disability.

It is the policy of Loadsmart that all offers of employment made shall be contingent upon successful completion of electronic background check(s). These checks will be job-related, consistent with business necessity and conducted by our vendor, pursuant to all applicable laws, rules, policies and procedures of our candidates' specific locale.