In this episode of the Fintech CTO Podcast, we’re joined by Keith Gregg, Founder and CEO of Chalice Connect—a B2B marketplace platform designed to empower small businesses with the tools, services, and resources they need to grow and scale. Hosted by Vasyl Soloshchuk, CEO of INSART, the conversation explores the power of digital marketplaces, the challenges of building two-sided platforms, and how fintech innovation can better serve small business owners.
Building the “Holy Grail” Marketplace for Small Businesses
Keith shares the inspiration behind Chalice Connect and how his decades of experience in financial services led him to identify a major gap in the market. Small business owners often struggle to access the resources needed to start, run, protect, and eventually monetize their businesses. Chalice Connect was created as a centralized platform that aggregates and integrates essential services—from CRM, payroll, and HR tools to legal, compliance, and cybersecurity solutions—giving entrepreneurs a single destination to manage their business lifecycle.
The Power of B2B Marketplaces
The discussion highlights why marketplace platforms are among the most powerful business models in modern technology. Keith explains how Chalice Connect connects software vendors and service providers with small business customers, enabling companies to access enterprise-level tools and benefits at affordable prices through collective buying power.
Pivoting Through COVID and Scaling the Platform
Keith reflects on the company’s journey since launching in 2019, including the challenges of navigating the COVID era. During this time, Chalice Connect pivoted its model from a direct marketplace to an enterprise licensing platform—allowing organizations, associations, and enterprises to create their own white-labeled digital marketplaces powered by Chalice technology.
Enterprise Licensing and Multiple Revenue Streams
Chalice Connect operates through several revenue channels, including enterprise licensing, subscription memberships, and marketing partnerships. Keith shares examples of how large organizations can leverage the platform to create digital marketplaces that deliver benefits, discounts, and services to their communities—opening new opportunities for both vendors and customers.
Solving the Small Business Resource Gap
A key theme of the episode is the underserved nature of the small business market. With more than 34 million small business owners in the United States, Keith emphasizes that many lack access to enterprise-grade resources. Chalice Connect aims to bridge this gap by offering solutions such as group health insurance access, software integrations, and professional services that are typically unavailable to small independent businesses.
From Industry Veteran to Startup Founder
Keith reflects on his entrepreneurial journey and how Chalice Connect represents the next chapter in his career. After decades in financial services leadership, he set out to build a platform that embodies his philosophy of “doing well by doing good”, creating value for entrepreneurs while building a sustainable and scalable technology company.
About Keith Gregg
Keith Gregg is a veteran financial services executive and entrepreneur with more than three decades of industry experience. Prior to founding Chalice Connect, he launched and led several successful financial firms and served in leadership roles across the investment advisory ecosystem. Through Chalice Connect, he is focused on building a digital infrastructure that helps small businesses access the tools and services needed to thrive.
A Note on Our Platform
The Fintech CTO Podcast explores the people, ideas, and technologies shaping the future of financial services. While we highlight fintech innovators and industry insights, we do not provide investment advice or professional consulting services.
