Director of Risk

About Bobtail

Bobtail is dedicated to increasing happiness by eliminating inefficiencies in the supply chain. We envision a supply chain without friction, fraud, waste, and abuse where companies succeed based on the value they create.

Bobtail is dedicated to increasing happiness by eliminating inefficiencies in the supply chain. We envision a supply chain without friction, fraud, waste, and abuse where companies succeed based on the value they create.

We work in a unique way at Bobtail, where we value teams over individuals and encourage experimentation and iteration to constantly improve. Teams are given flexibility in working towards a shared purpose and given the freedom to decide how they will accomplish their goals.

If you are an out of the box thinker that takes a proactive approach in collaborating with others to solve problems and achieve your goals - we would love to talk to you.

• Mission
• Teams over individuals
• Collaboration
• Communication
• Iteration
• Experimentation and failing fast
• Initiative and solutions oriented approach
• Documentation
• Data
• Mental health and work life balance
• Diversity
• Transparency

We are seeking an experienced Director of Risk to lead and strengthen our risk, underwriting, fraud prevention, and compliance functions within the freight factoring industry. This individual will take ownership of the company's risk function, including leading and developing the existing risk team, establishing clear standards and accountability, and ensuring the organization has the people, processes, controls, and analytics necessary to effectively manage risk as the business grows.

The ideal candidate will have deep knowledge of the trucking and transportation industry, with hands‑on experience in client and debtor risk, KYB/KYC, UCC, invoice verification, fraud detection, and portfolio management. This individual will be highly data‑driven and analytical, with the ability to identify patterns, develop risk models and analytics, and design scalable workflows and controls that protect the company against fraud and losses while supporting responsible growth.

We are looking for a strong leader and risk decision‑maker who can create a culture of sound judgment, ownership, and accountability. The role requires the ability to move comfortably between strategic leadership and hands‑on problem solving, and to effectively lead a distributed team in a remote work environment.

You should apply if you have:

• Bachelor's degree in Business, Finance, or a related field.
• 7+ years of experience in risk, underwriting, fraud, or compliance, including leading a risk or underwriting function.
• Strong experience in the trucking/freight industry is required.
• Demonstrated experience managing and developing teams, including setting expectations, coaching staff, managing performance, and building team capabilities.
• Experience with KYB/KYC, UCC, client/debtor risk, and invoice verification.
• Strong understanding of fraud detection, portfolio risk, aging, and dilution.
• Highly analytical and data‑driven, with strong pattern‑recognition and problem‑solving skills.
• Experience developing risk models, analytics, controls, and fraud‑prevention workflows.
• Strong risk judgment and ability to make timely decisions in situations where information may be incomplete or ambiguous.
• Ability to establish clear risk policies, approval authorities, escalation standards, and accountability across a risk organization.
• Experience identifying gaps in existing processes and teams and implementing practical improvements.
• Strong communication and cross‑functional leadership skills, including the ability to clearly communicate risk issues and recommendations to senior leadership.
• Comfortable managing offshore and distributed…