Vice President, People

Flock Freight • Chicago, IL

7d • $215,000 - $243,000 • Hybrid

About The Position

Flock Freight is a FreightTech company that uses patented technology to move freight more efficiently, reliably, and sustainably. The company’s guaranteed terminal-free truckload service, FlockDirect, finds the best options to pool freight among billions of possible combinations, optimizing routes while finding and filling trucks’ empty spaces. Shipments stay safe in a single truck, driven by a single driver, all the way to their destination allowing shippers to only pay for the space they need and enabling carriers to earn more from every linear foot of capacity — all while slashing carbon emissions by up to 40% compared to traditional shipping methods. Flock Freight has been a Certified B Corp since 2020, meeting high social, environmental, transparency, and accountability standards to all of our stakeholders. If you’re looking for the opportunity to make a difference then you’ve come to the right place. We’re looking for folks that are innovative, love collaborating in a fast-paced environment, and find joy and excitement in doing the hard work. If that sounds like you then keep on reading and see if this role is the one for you. Team/Department Overview: People Team- Reporting to the General Counsel The mission of the VP, People is to continue to build and lead a high-impact People function that strengthens Flock Freight’s leadership, drives a corporate wide high performance culture, and ensures the organization is structured and equipped to scale into its next phase of growth. They will design and implement the systems, talent strategy, and performance standards required for a late-stage, high-growth company operating across onshore and offshore teams. By doing so, they will enable the Executive Leadership Team to make disciplined talent decisions, increase organizational effectiveness, and build a culture of accountability, engagement, and performance.

Requirements

• 12–15+ years of progressive HR/People leadership experience, including at least 5+ years leading a multi‑discipline People function (HRBP/employee relations, Total Rewards, Talent Acquisition, People Development/L&D).
• Experience owning the People strategy for a 200–600+ person organization in a late‑stage, high‑growth or PE/VC‑backed environment.
• Proven track record as Head of People / VP People or equivalent role, partnering closely with CEO, GC, President, COO, etc.
• Demonstrated success building and scaling People systems and processes (performance management, succession planning, workforce planning, compensation & benefits, manager enablement).
• Hands-on experience with multi‑state U.S. employment; strong grounding in core HR compliance (employment law, wage & hour, terminations, investigations).
• Proven experience leading onshore + offshore / BPO or globally distributed teams and navigating cultural and time‑zone differences.
• Strong data orientation: comfortable using HRIS/people analytics to inform headcount plans, organizational design, and talent decisions.
• Experience designing and implementing compensation and benefits programs that balance cost discipline with talent competitiveness.

Nice To Haves

• Prior experience in technology, logistics, supply chain, or other operations‑intensive industries.
• Experience presenting People metrics and org updates to a C-suite, Board and/or compensation committee.
• SPHR, SHRM‑SCP, or similar advanced certification (nice to have, not required).

Responsibilities

• People Strategy
• Organizational design aligned to business strategy
• Workforce and capacity planning
• Resource deployment and headcount rigor
• Leadership development and succession planning
• Culture, values, and change leadership
• Talent & Performance
• Talent attraction and resourcing strategy
• Performance management systems and accountability frameworks
• Career pathing and development architecture
• Executive coaching and proactive leadership partnership
• Engagement and retention strategies
• Total Rewards & Compliance
• Compensation and benefits strategy aligned to financial discipline and market competitiveness
• Multi-state and international HR compliance
• Risk mitigation and employment governance
• HRIS and People analytics strategy
• People Operations & Infrastructure
• Scalable People systems optimized for a 450+ global workforce
• Process design to enable operational excellence
• People technology and workflow automation
• Board-level reporting and metrics
• Team Leadership
• You will directly lead a multi-disciplinary People Team, including:
• HRIS & Total Rewards Manager
• HR Manager (Open Role)
• Senior People Development Partner
• Talent Acquisition Partner

Benefits

• Hybrid Work Model: As an organization we value in-office collaboration, working cross-functionally, and winning together. Through scheduled in-office and work from home days, we are able to work more efficiently and collaboratively as an organization.
• 401(k): Flock provides access to a 401(k) retirement savings plan to help you prepare for the future.
• Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided.
• This role may be eligible to participate in Flock Freight’s equity plan and corporate bonus plan.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed