Head of IT & Corporate Systems - IT & Corporate Systems

Company Overview

Flock Freight is the largest Shared Truckload (STL) freight brokerage in the U.S., transforming underutilized truckload capacity into tangible value: cost savings for shippers, increased earnings for carriers, and a smaller carbon footprint.

Their AI-powered, patented pooling technology optimizes across Flock’s entire customer network, combining shipments from thousands of businesses into efficient Shared Truckloads. With STL, shippers enjoy truckload-level service while only paying for the space they need. Trusted by thousands of customers, from some of the largest enterprises to growing brands, Flock Freight delivers an unmatched combination of cost efficiency, exceptional service, and a streamlined shipping experience.

Flock Freight has been a Certified B Corp since 2020, meeting high social, environmental, transparency, and accountability standards to all of our stakeholders.

Team/Department Overview

IT & Corporate Systems supports the employees, applications, and workflows that run Flock Freight. The team brings together corporate IT and enterprise-applications specialists, partnering closely with Finance, RevOps, Operations, People, and Engineering. This role reports directly to the Senior Director, Engineering Infrastructure.

About the Role:

We’re looking for a hands-on Head of IT & Corporate Systems to lead a lean team and take full ownership of our internal technology function. You will set priorities, develop the team, own vendors and spend, and ensure employees and business teams have reliable, secure systems that help them do their best work.

Your scope includes employee IT, identity and endpoints, Salesforce, NetSuite, and the integrations connecting our business applications. You will remain technically engaged while guiding specialists and external partners, with the autonomy to run daily operations within agreed budgets and decision boundaries.

We intend to keep this team lean. You will increase its impact through coaching, simplification, self-service, and reliable automation and AI, rather than relying on significant headcount growth. This is an opportunity to shape how a technology-enabled, operations-heavy business works every day.

Core Responsibilities

Functional & People Leadership

• Own the IT and corporate-systems roadmap, operating cadence, service delivery, and day-to-day priorities and escalations.
• Coach and develop a small team, set clear expectations, manage performance, and establish dependable coverage for critical responsibilities.
• Partner with business leaders to resolve competing priorities and communicate clear decisions, service commitments, and delivery expectations.
• Remain actively involved in day-to-day IT operations, including troubleshooting, identity and access management, endpoint administration, and configuration of platforms such as Okta and Kandji (Iru). This is not a purely strategic or people-management position.

Corporate IT & Employee Experience

• Lead identity and access management, endpoint lifecycle, onboarding and offboarding, collaboration tools, office technology, and employee support.
• Improve cloud-first systems such as Okta, Google Workspace, Slack, Kandji (Iru), Intune, and endpoint-security tooling through consistent, auditable workflows.
• Establish practical service metrics, incident response, documentation, recovery practices, and backup coverage.
• Own endpoint security, access governance, incident response readiness, and business continuity planning.
• Maintain security controls and documentation that support applicable regulatory and government compliance obligations.

Corporate Systems & Integrations

• Own technical delivery and operations for Salesforce, NetSuite, and integrations connecting business applications with Flock’s platform.
• Partner with Finance, RevOps, and Operations on requirements, priorities, and acceptance criteria, while business owners retain accountability for their policies, processes, and controls.
• Guide specialists and external partners through configuration, integrations, testing, releases, and incident resolution; strengthen data integrity, monitoring, and recovery across platforms such as Celigo.

Automation & AI Enablement

• Eliminate repetitive requests and manual handoffs through self-service, APIs, scripting, and workflow automation, including reliable joiner, mover, and leaver processes.
• Apply AI where it produces measurable service or productivity improvements, with appropriate permissions, evaluation, auditability, and human oversight.
• Build maintainable automation with clear ownership, secure credentials, monitoring, and failure handling, partnering with Applied AI and Engineering on shared capabilities.

Vendors, Spend & Operational Controls

• Own the budget and software lifecycle within approved authority, including procurement, renewals, vendor performance, license utilization, and tool retirement.
• Partner with Finance and Legal on contracts and total operating cost, and with security and engineering stakeholders on access governance, endpoint protection, incident response, and audit readiness.
• Simplify the technology portfolio and reduce operational risk and single-person dependencies without adding unnecessary tools or process layers.
  
  

What Success Looks Like

• In your first 90 days, establish clear ownership, a focused roadmap, service and spend baselines, and dependable operating rhythms with the team and business stakeholders.
• Independently run routine priorities, escalations, and vendor decisions, with clear boundaries for material risks and executive decisions.
• Deliver an initial reliable automation or simplification and improve coverage for business-critical systems and integrations.
• Over time, demonstrate better employee service, more reliable business workflows, less manual effort, and disciplined spend while maintaining a lean team.

Qualifications

Required

• Approximately 5–10 years of relevant professional experience, including 2–3 years leading corporate IT operations and managing employees.
• Experience supporting a small to midsize organization, ideally in a startup or growth-stage environment with a modern, cloud-first technology stack.
• Experience independently leading a corporate IT or business-technology function, including people management, priorities, vendors, budgets, and cross-functional relationships.
• A track record of leading a small team while remaining technically engaged and improving results without relying primarily on headcount growth.
• Strong hands-on knowledge of modern identity, SaaS administration, endpoint management, access controls, and employee lifecycle workflows.
• Demonstrated production automation or integration delivery using APIs, scripting, or workflow platforms, including monitoring, failure handling, and secure credential management.
• Experience governing business applications and cross-functional workflows, with an understanding of CRM, ERP, data integrity, testing, and change-control risks.
• Sound commercial judgment, supported by examples of vendor negotiation, license optimization, tool consolidation, or cost avoidance.
• Clear communication, a service-oriented mindset, and the judgment to make decisions independently while escalating material business risks appropriately.

Preferred

• Okta, Google Workspace, Slack, Kandji, Intune, CrowdStrike, or equivalent cloud-first IT tooling.
• AI-enabled support, enterprise search, knowledge management, or workflow automation with measurable production outcomes.
• Salesforce, NetSuite, Celigo, or comparable CRM, ERP, and integration platforms. You do not need to be the deepest administrator of every platform, but you should be able to evaluate designs and own results.
• Experience supporting distributed employees and multiple offices, partnering with Finance on operational workflows and controls, and strengthening audit readiness within a lean team.

CompensationThe base salary range for this position is $175,000 - $210,000 per year + annual bonus. This reflects typical earning potential in this role based on market data and individual factors including skill sets, experience, and geographic location. In addition to 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.

Life & Benefits Of The 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.
• Medical, Dental & Vision: Generous coverage for employees and dependents. Both HMO and PPO options provided.
• Additional Benefits and Perks: We are proud to offer additional benefits to our employees, including but not limited to paid parental leave, commuter benefits, and a monthly technology stipend.

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 but not limited to 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!

We are targeting talent in the San Diego/Encinitas area.