CEO Insights: Ben Clarke, Founder and Co-CEO, Goodwin

Ben began his career at the intersection of computer science and entrepreneurship, founding a company during college that was pioneering in cloud computing. The company focused on migrating tethered applications to the cloud—well before the technology became mainstream—and was successfully sold, marking his first exit.

In the following chapter, Ben founded The Shipyard, a breakthrough venture in digital media trading. The company became a trusted partner to many of the Finance 100, helping redefine performance marketing through algorithmic optimization and precision analytics. This work brought him deeper into financial markets and the insurance industry. In 2018, The Shipyard took an investment from KKR, and later Alaris Investment Partners – helping it become one of the largest independent agencies in America.

In 2016, Ben launched Bold Penguin, which grew into the largest commercial insurance exchange in the United States. The platform transformed how brokers and carriers triaged, quote, and bound small commercial insurance policies, becoming foundational technology infrastructure for the industry. Bold Penguin was sold in 2021 in one of the largest insurtech acquisitions of the decade. Post acquisition, Ben built the first AI system in insurance to full automate large commercial insurance underwriting – today it is the largest provider automating millions of policy analyses per year.

Building on his track record of scaling complex industries through software, Ben founded Goodwin in 2024, a company developing optimization software for the private aviation market. Goodwin has grown 700% YoY and has built a variety of capabilities in sourcing, proposals and payments including a full bank-stack solution.

Across each venture, Ben has consistently applied a forward-looking approach—identifying opportunities to simplify complex systems, automate workflows, and unlock new possibilities through technology and data-driven strategy.