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Vice President, People

Flock Freight

Flock Freight

People & HR
Chicago, IL, USA
Posted on Feb 24, 2026

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.

What You’ll Do:

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

Who you Are

  • 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.

Preferred Experience

  • 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).

Role based in Encinitas, CA with a hybrid in‑office model (Monday, Tuesday, Thursday in office; Wednesday and Friday WFH, with occasional full‑week in‑office cadence as business needs dictate).

Life & Benefits at Flock:

  • 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.

Compensation

The expected base salary range for this position is $215,000 to $243,000 and an additional yearly variable bonus based on individual and company performance. This reflects market data and individual factors, including skill sets, experience, and geographic location. In addition to base salary, full-time employees are eligible for an equity package and competitive benefits that support you and your family as part of your total rewards package at Flock Freight. Specific details will be shared during the interview process.

Our promise to you:

Flock Freight is committed to creating an environment that’s fair and inclusive. We fill our open positions based on qualifications, merit, and business needs. We value the skills of people from all backgrounds and are proud to hire, promote, and retain talent from a diverse candidate pool. Diverse perspectives are central to innovation at Flock Freight and make our team better. We're interested in your inherent abilities, not just the skills you bring from your last role - if you think you have what it takes to succeed in the role but don't check every box, please still get in touch. We'd love to start a conversation with you.

Flock Freight has zero tolerance for behavior that negatively impacts marginalized groups, including women, people of color, veterans, immigrants, people with disabilities, and members of the LGBTQIA+ community. We invite people of all identities to join the Flock!