Director of Risk Management at Bobtail

About Bobtail

Bobtail is dedicated to enhancing happiness by eliminating inefficiencies throughout the supply chain. We envision a future supply chain free from friction, fraud, waste, and abuse, where companies succeed based on the true value they create.

Our approach at Bobtail is unique; we prioritize teams over individuals and champion continuous experimentation and iteration for constant improvement. Teams are empowered with flexibility to work towards a shared purpose and granted the autonomy to decide how to achieve their goals.

If you are an innovative thinker who proactively collaborates with others to solve problems and achieve objectives, we would love to connect with you.

Our Core Values:

• Mission-driven focus
• Teams over individuals
• Strong collaboration
• Effective communication
• Continuous iteration
• Experimentation and learning quickly from failures
• Taking initiative and maintaining a solutions-oriented approach
• Thorough documentation
• Data-driven decision making
• Prioritizing mental health and work-life balance
• Embracing diversity
• Promoting transparency

Director of Risk Management Opportunity

Bobtail is actively seeking an experienced Director of Risk to lead and strengthen our critical risk, underwriting, fraud prevention, and compliance functions within the freight factoring industry. This individual will take full ownership of the company’s risk framework, including leading and developing the existing risk team, establishing clear standards and accountability, and ensuring the organization possesses the necessary talent, processes, controls, and analytics to effectively manage risk as the business scales.

The ideal candidate will bring deep knowledge of the trucking and transportation sector, coupled with hands-on experience in client and debtor risk, Know Your Business (KYB)/Know Your Customer (KYC) protocols, Uniform Commercial Code (UCC) compliance, invoice verification, advanced fraud detection, and robust portfolio management. This role demands a highly data-driven and analytical professional capable of identifying patterns, developing sophisticated risk models and analytics, and designing scalable workflows and controls. The primary objective is to protect the company against fraud and losses while strategically supporting responsible business growth.

We are searching for a strong leader and decisive risk decision maker who can cultivate a culture of sound judgment, ownership, and accountability. This position 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.

Key Responsibilities

• Risk Function Leadership: Own the comprehensive risk function, establishing its strategy, priorities, operating standards, and the overall risk management framework for the business.
• Team Leadership & Development: Lead, coach, and develop the risk team; set clear roles and expectations while building strong risk judgment and decision-making capabilities across the team.
• Organizational Design & Capacity: Evaluate the structure, skills, and capacity of the existing risk organization and recommend and implement changes to ensure the team is optimally staffed and equipped to support business growth.
• Client & Debtor Risk: Proactively assess and monitor client and debtor credit risk, exposure levels, concentrations, and emerging portfolio risks.
• Underwriting Oversight: Oversee KYB/KYC processes, UCC compliance, and risk-based client onboarding and approvals, including appropriate approval authorities and escalation procedures.
• Fraud Detection & Prevention: Identify suspicious activity, patterns, and emerging fraud risks, ensuring the team responds quickly and consistently to potential issues. Create scalable workflows and controls to prevent fraud and minimize losses.
• Invoice Verification: Develop and manage risk-based controls for invoice approval and verification, carefully balancing fraud prevention with operational efficiency.
• Portfolio Management: Establish a disciplined portfolio management process for continuous monitoring of aging accounts, dilution, concentrations, exceptions, and overall portfolio quality.
• Risk Models & Analytics: Build and enhance risk scoring methodologies, reporting, Key Risk Indicators (KRIs), and data-driven decision tools.
• Strategic Risk Partnership: Collaborate with senior leadership and cross-functional teams to balance effective risk management with responsible growth, providing a clear risk perspective on significant business decisions.

Qualifications and Experience

• Bachelor’s degree in Business, Finance, or a related field.
• Minimum of 7 years of progressive experience in risk, underwriting, fraud, or compliance, including significant time leading a risk or underwriting function.
• Strong experience in the trucking/freight industry is a mandatory requirement.
• Demonstrated experience managing and developing teams, including setting expectations, coaching staff, managing performance, and building team capabilities.
• Expertise with KYB/KYC, UCC, client/debtor risk, and invoice verification.
• Profound understanding of fraud detection, portfolio risk, aging analysis, and dilution control.
• Highly analytical and data-driven, with strong pattern-recognition and complex problem-solving skills.
• Extensive experience developing risk models, analytics, controls, and fraud-prevention workflows.
• Strong risk judgment and the 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 articulate risk issues and recommendations to senior leadership.
• Comfortable managing offshore and distributed teams in a fast-paced, fully remote environment.
• Willingness to be hands-on when necessary while building a team capable of independently managing day-to-day risk activities.

Benefits and Perks

• Generous Paid Time Off (PTO)
• Monthly Mental Break Day
• Comprehensive Parental Leave program
• Robust Healthcare Coverage
• Life Insurance
• 401(k) with Company Match
• Flexible Work-from-Home (or Anywhere) Policy

At Bobtail, creating a diverse and inclusive workplace is fundamental to our core identity. We are an equal opportunity employer and actively welcome individuals from all backgrounds, cultures, religions, national origins, races, colors, genders, gender expressions, sexual orientations, ages, marital statuses, veteran statuses, experiences, abilities, and perspectives.