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. 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. The things we value: 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 teams in a fast-paced, remote environment. Willingness to be hands-on when necessary while building a team capable of independently managing day-to-day risk activities. You will be responsible for: Risk Function Leadership : Own the overall risk function and establish the strategy, priorities, operating standards, and risk management framework for the business. Team Leadership & Development : Lead, coach, and develop the risk team; establish 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 changes to ensure the team is appropriately staffed and equipped to support the business. Client & Debtor Risk : Assess and monitor client and debtor credit risk, exposure, concentrations, and emerging portfolio risks. Underwriting : Oversee KYB/KYC, UCC, 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, and ensure 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, balancing fraud prevention with operational efficiency. Portfolio Management : Establish a disciplined portfolio management process for monitoring aging, dilution, concentrations, exceptions, and overall portfolio quality. Risk Models & Analytics : Build and improve risk scoring, reporting, KRIs, and data-driven decision tools. Risk Strategy : Partner with senior leadership and cross-functional teams to balance risk management with responsible growth, and provide a clear risk perspective on significant business decisions. Benefits: Generous PTO Monthly Mental Break Day Parental leave Comprehensive healthcare coverage Life insurance 401k with company match Work from home (or wherever) Creating a diverse and inclusive workplace is Bobtail’s nucleus. We are an equal opportunity employer and embrace people of different backgrounds, cultures, religions, national origins, races, colors, genders, gender expressions, sexual orientations, ages, marital status, veteran status, experiences, abilities and perspectives.