Director of Risk Management

Director of Risk Management

MISSION

Build PLS's enterprise risk management function from the ground up — partnering with Legal, insurance brokers/carriers, and executive leadership to identify, quantify, and mitigate organizational, insurance, and litigation risk, including the elevated broker-liability exposure created by Montgomery v. Caribe Transport II — and to design the organizational structure needed to manage that risk on an ongoing basis.

OUTCOMES (YEAR ONE)

1. Complete a comprehensive risk assessment across PLS entities within 90 days.

Evaluate insurance coverage adequacy (cargo, auto liability, broker/contingent liability, E&O, cyber), litigation and claims exposure, and organizational/operational risk across both entities post-merger, and present prioritized findings to the President and executive team.

1. Design and stand up PLS's enterprise risk management (ERM) framework and organizational structure within 6 months.

Define risk ownership, escalation paths, and a reporting cadence to the President and executive team; recommend where the risk function sits organizationally as PLS scales.

1. Hire, onboard, and stand up a risk management team within 6–9 months.

Build the team needed to run claims handling, insurance program administration, and ongoing risk analytics without President-level involvement.

1. Build and operationalize a negligent-selection/broker-liability defense strategy with Legal within 6 months.

In direct response to Montgomery v. Caribe Transport II, partner with the Director of Carrier Compliance and legal counsel to establish documentation standards, litigation-readiness protocols, and a coordinated response plan for negligent-hiring and broker-liability claims.

1. Optimize the company's insurance program and reduce total cost of risk by [X]% within 12 months (baseline to be established in month 1–2).

Review and renegotiate cargo, auto liability, broker liability, cyber, and E&O coverage with brokers/carriers to close gaps identified in the initial risk assessment while managing overall premium and retained-risk cost.

1. Launch a live risk register with quarterly executive reporting within 6 months, ongoing thereafter.

Track identified risks, mitigation owners, status, and residual risk ratings; report quarterly to the President and executive team.

COMPETENCIES

• Honesty/Integrity — Gives leadership an unvarnished view of organizational risk, even when it is uncomfortable.


• Analysis Skills — Quantifies exposure across insurance, litigation, and operational risk to prioritize what matters most.


• Strategic Thinking — Translates a fragmented risk landscape into an organizational structure and multi-year mitigation strategy.


• Building Relationships — Builds trusted working relationships with Legal, insurance brokers/carriers, and executive leadership to execute strategy collaboratively.


• Persuasion/Negotiation — Negotiates coverage terms with insurance carriers and builds internal buy-in for new risk controls.


• Organization and Planning — Sequences a build-out spanning assessment, structure design, team hiring, and insurance renegotiation.


• Proactivity — Identifies and moves to mitigate emerging risks before they become claims or litigation.


• Composure Under Pressure — Stays level-headed and decisive when managing active claims, litigation, or crisis-level exposure.

Bracketed [X]% targets are placeholders pending baseline data (fraud/incident rates, current total cost of risk) — to be finalized with the President in the first 30–60 days.