Chief People Officer


Chicago, IL, USA

Full time

$200-220k (annually)

Chief People Officer / CXO

Apr 13

This job is no longer accepting applications.


→ Do you have experience scaling HR/People functions at hyper-growth companies?

→ Do you believe in game-changing innovations and are excited about reimagining an 800 billion dollar industry?

→ Do you want to work on an Executive team where you’re treated like an adult but have fun like a kid? 

If so, nice to meet you! We are Loadsmart and we have recently opened a VP, People (Head of HR) position to help attract and retain top talent at our growing company (we grew from 150 to 700+ in the last two years). This role is both exciting and intense, with still a ton to build and execute as we continue to grow to over 1,000 Loadies in 2022! We are looking for an exceptional leader who is both strategic and hands-on that will partner with the CEO and senior leadership to define and execute the HR strategy. 

LOCATION: This position must be based in Chicago and is expected to come to the office at least 4 days per week.


  • Drive the strategic design and execution of the company's People programs and initiatives by leading/coaching the HR team to create a high-performing culture tied to our company values
  • Build strategic partnerships with senior leadership and management to develop solutions for their business objectives and challenges, navigate change management and optimize the organizational design with the right people in the right roles 
  • Design the people growth strategies and initiatives to ensure retention and growth of high potential employees as well as developing rigor around performance management and ongoing top-grading for those employees who may not be performing at optimal levels
  • Implement Talent Acquisition best practices to build out the recruiting plan, the strategies to source the best talent and enhance our employer brand
  • To craft roles based on market availability and business needs, partner to build assessments to evaluate competencies and skills and enhance the overall employment brand to drive top talent to join us
  • Operationalizing workforce planning and human capital budget alignment
  • Identify key metrics and performance indicators to assure growth and development in the company. 
  • Provide insights and implement best practices for our Talent Acquisition team, partner with the team to build out the recruiting plan, the strategies to source the best talent and build out our employer brand.
  • Ensuring we create and document consistent policies, processes, communications and calendars for global HR programs that mitigate risk by proactively aligning compliance with the country/state requirements and handling internal employee relations issues
  • Prepare relevant materials for the Board of Directors


  • Leading HR functions (including Talent Acquisition and People Ops) at growing, international, pre-IPO companies where you were responsible for building frameworks and programs from scratch (or significantly iterating) 
  • Successfully challenging an organizational approach with a solution-driven mindset that delivers ROI-driven improvements to organization design, performance management, career paths, compensation structures and other identified areas of opportunities 
  • Developing clear plans and communications for all stakeholders, including the Board, senior leadership, management and program participants; one of our core values is Clarity and making sure our Loadies understand our programs is paramount
  • Knowledge of and commitment to HR best practices in employee retention, compensation and benefits management, conflict resolution, program implementation and employment law (including but not limited to ADA, FLSA, and FMLA); global HR laws not as critical but the ability to learn/understand them is important


  • A superstar who leverages exceptional instincts/experiences leveraging HR programs to drive business outcomes and financial results (Some companies might call this a required Masters or “MBA”; we need someone who understands business and don’t care where you learned it!)
  • A self-starter, innovative, result-focused and team-oriented
  • Possessing a growth mindset, sense of curiosity and strong problem-solving skills; you are constantly learning about emerging market trends to identify potential opportunities and gaps
  • Tech-savvy including ability to leverage (learn, if necessary) collaboration tools including Google Suite and Slack as well as navigate core HR Systems (Bamboo, Lever) 
  • Being analytical with stellar problem-solving skills including the ability to make recommendations by using judgment that is consistent with company culture as well as standards, practices, policies, procedures or governing law
  • A practitioner with strong attention to detail, organization, and the highest standards for accuracy and precision



• Base salary between $200,000 - $220,000 based on experience

• Annual 30% cash variable incentive tied to overall company performance

• Extremely competitive Equity package - both an initial grant at sign-on and additional rewards as part of the annual variable program 

• 401k Match up to $5,000 regardless of salary

Good Health 

• Comprehensive Medical, Dental, and Vision insurance plans

• Short and Long Term Disability Insurance covered 100% by the company

• Teledoc (remote doctors) and Talkspace (mental health counseling) membership fees covered 100% by the company

• Commuter benefits and membership with CITI/Divvy bike 

...And Happiness

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

• Lots of employee engagement activities both offsite and onsite 

• Work with an inclusive, global community of Loadies across 15 countries united by our core value of Teamwork

• Regular recognition, feedback, and transparency across all levels; we offer monthly Business Updates, monthly "Ask Me Anything" Sessions with the CEO and Quarterly Equity updates

• Opportunities for you to join our community service initiatives and donation drives

Are you up to the challenge? Apply today!

JOB TYPE: exempt

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.

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Loadsmart aims to move more with less. We combine great people and innovative technology to more efficiently move freight throughout North America.