In this episode, Steve and Sam are joined by special guest Clint Oram, who recently left SugarCRM after exactly 21 years.
The group explores the future of CRM, the transformative power of AI, and how technology is reshaping the way organizations think about customer relationships, system design, and collaboration.
Topics
- AI as a Personal Assistant: How generative AI will fundamentally change CRM by doing more than just automation—by anticipating, advising, and acting on behalf of users.
- Breaking Down Silos: Why the concept of standalone CRM, ERP, and email systems may soon disappear in favor of integrated AI-driven experiences.
- Security in the Age of AI: Where AI meets data privacy—and the tension between internal collaboration and external threats.
- Rise of No-Code and “Vibe Coding”: How rapid prototyping and AI-powered development environments are changing who can build software—and how fast.
- Micro-Verticals and CRM Strategy: The growing need for CRM solutions tailored to specific industries and sub-industries (yes—even cookie manufacturers).
- Clint’s Product Wisdom: From Sugar’s AI-powered opportunity summaries to calculated fields, Clint reflects on the most impactful CRM features he’s helped build.
- Advice for New Tech Founders: Why differentiation, ongoing innovation, and AI literacy are the new cornerstones of a successful go-to-market strategy.

Episode Highlights
00:00 – Clint reflects on 21 years at SugarCRM
01:30 – CRM meets AI: The personal assistant vision
04:00 – The challenge of small data and AI’s potential to unify disconnected systems
08:00 – Security, privacy, and collaboration
12:00 – AI-generated apps and the prototyping revolution
18:00 – No-code’s evolution and its impact on software engineering
22:00 – Best features from Clint’s SugarCRM tenure
24:00 – How to choose the right CRM in 2025 and beyond
27:00 – Micro-verticalization and customizing CRM
30:00 – Advice for the next generation of software entrepreneurs