“Always Assume Positive Intent.”
Cole Wilson is a dynamic operations executive and strategic leader whose career has been defined by his ability to build, scale, and optimize complex business systems across the logistics, technology, e-commerce, and consumer packaged goods (CPG) sectors. With over a decade of professional experience, Cole has consistently demonstrated a unique blend of analytical rigor, operational excellence, and forward-thinking leadership. His guiding philosophy, “Always assume positive intent,” reflects a leadership style rooted in collaboration, accountability, and trust—qualities that have enabled him to drive meaningful impact across every organization he has served.
Currently, Cole serves as Co-Founder and Chief Operating Officer of a stealth startup based in Los Angeles, where he is responsible for architecting and executing the company’s operational strategy. In this role, he oversees critical business functions including inventory management, demand planning, fulfillment, financial operations, and marketplace strategy. From the ground up, Cole is building the infrastructure necessary to support scalable growth, ensuring that operational processes not only meet current demands but are designed to evolve alongside the business. His hands-on leadership approach allows him to seamlessly integrate strategy with execution, positioning the company for long-term success.
Before stepping into the entrepreneurial space, Cole spent more than six years at Flexport, a global leader in logistics and supply chain technology. During his tenure, he held a variety of leadership roles spanning business operations, sales operations, and client solutions, gaining a comprehensive understanding of the end-to-end supply chain ecosystem. His ability to navigate complex operational challenges while aligning cross-functional teams made him a key contributor to the organization’s growth and innovation.
As a Senior Manager in Business Operations, Cole played a pivotal role in driving data-informed decision-making across the organization. He developed and managed sophisticated dashboards using Looker, providing leadership teams with real-time visibility into revenue drivers, operational performance, and profitability metrics. His expertise in financial modeling and scenario planning enabled the company to forecast growth, allocate resources effectively, and operate strategically even within constrained budgeting environments.
Cole’s experience within Flexport’s Commercial Leadership Development Program further solidified his reputation as a high-impact leader. During an international rotation in Copenhagen, he managed a team of ten professionals, successfully training new hires, onboarding mid-market clients, and improving operational efficiency by 50%. His ability to lead in a global context, combined with his cultural adaptability and working proficiency in Spanish, underscores his effectiveness in diverse and dynamic business environments.
In earlier roles at Flexport, Cole managed a portfolio of over 40 clients representing more than $30 million in annual recurring revenue. He was responsible for the full client lifecycle, from onboarding and implementation to growth and retention. His work included designing standardized operating procedures, leading quarterly business reviews, and partnering with product and engineering teams to enhance platform functionality. Through these efforts, Cole not only improved client satisfaction but also strengthened the company’s operational foundation.
Cole began his career in strategy consulting at Cartesian, where he developed a strong analytical foundation in market research, financial forecasting, and strategic planning. Working with clients in the telecommunications and technology sectors, he conducted market sizing analyses, built operating models, and contributed to the development of growth strategies informed by data and industry insights. This early experience continues to influence his structured approach to problem-solving and decision-making.
Academically, Cole holds a Bachelor of Science in Business Administration with a concentration in Finance, as well as a Bachelor of Arts in Economics, both from Boston University’s Questrom School of Business. His educational background complements his professional experience, equipping him with a deep understanding of financial systems, market dynamics, and economic principles that inform his strategic thinking.
Beyond his technical expertise, Cole is known for his intellectual curiosity and disciplined mindset. His personal interests—including crosswords, strategy board games, and film—reflect a passion for critical thinking, pattern recognition, and storytelling. These qualities translate into his professional life, where he approaches challenges with creativity, precision, and a long-term perspective.
Cole is now seeking opportunities to contribute at the board level, where he can leverage his experience in scaling businesses, building operational infrastructure, and driving strategic growth. Having successfully co-founded and developed a brand that resonates with consumers, he brings firsthand insight into the challenges and opportunities faced by emerging companies. His ability to bridge strategy and execution makes him a valuable advisor to organizations looking to navigate growth, optimize operations, and achieve sustainable success.
With a proven track record of leadership, a commitment to continuous improvement, and a collaborative approach to problem-solving, Cole Wilson stands out as a forward-thinking executive ready to make a meaningful impact at the board level. His career reflects not only professional achievement but also a deep commitment to building organizations that are efficient, resilient, and purpose-driven.
Character:
Cole demonstrates integrity and professionalism in every aspect of his work, consistently fostering trust among colleagues and stakeholders. He approaches challenges with a mindset rooted in accountability and optimism, guided by his belief in assuming positive intent. His ability to remain composed and solution-oriented under pressure highlights his strong personal character and leadership maturity.
Knowledge:
He possesses a deep and well-rounded understanding of operations, logistics, financial modeling, and strategic planning. His experience across consulting, global logistics, and startup environments enables him to bring both theoretical and practical insights to complex business challenges. He continuously applies data-driven methodologies to inform decisions and improve organizational performance.
Strategic:
Cole excels at translating high-level vision into actionable strategies that drive measurable results. He has a proven ability to design scalable systems, optimize processes, and align cross-functional teams toward shared objectives. His strategic mindset allows him to anticipate challenges, identify opportunities, and position organizations for sustainable growth.
Communication:
An effective communicator who can distill complex ideas into clear, actionable insights for diverse audiences. He fosters alignment across teams by promoting transparency, collaboration, and shared understanding. His ability to engage stakeholders and lead productive discussions strengthens both internal operations and external partnerships.
