E20: In Stealth Mode with Jacob Posel

In this episode of The SAAS Operators Podcast, we sat down with Jacob Posel to talk about his journey navigating the earliest stage of building a SAAS business and how he is thinking about AI, distribution and product-market fit.
Jacob shares why chasing the “biggest opportunity” is not enough without obsession. How his background in marketing and advertising gives him an edge. He explains why stealth mode matters, how he is thinking about first hires, and why great tech is still the foundation of any surviving SAAS business.
We talk about Icon’s controversial move into managed services, whether software as a service companies are destined to become... just service companies, and the reputational risks of overpromising when you only get so many first impressions. From cycle times in SAAS, to the important of momentum, and how AI is changing the way founders meddle directly in product development, this conversation is an exploration of how SAAS businesses starting today in 2025 operate.

00:00 The Trade-offs of Statins and Health Choices
01:20 Marketing Trends and the Zeitgeist
04:14 Building a SaaS Company: Insights from Jacob
06:50 Navigating the SaaS Landscape with AI
09:48 The Future of Software: Managed Services vs. Tools
15:22 Icon's Managed Service Offering and Industry Reactions
23:16 The Impact of Pricing on Business Strategy
26:49 Technology vs. Human Intervention in Service Delivery
29:47 Cultural Expectations and Employee Engagement
33:56 Product Reliability and Market Trust
37:36 Consumer Journey and First Impressions
42:48 The Role of AI in Business Operations