In SaaS leadership and product development, values often outlast culture. Few journeys highlight this better than Stefano Grossi’s path from firefighter to technologist, FreshBooks CPTO, and founder of Branco.ai. In this episode of SaaS That App: Building B2B Web Applications, Aaron Marchbanks discusses with Stefano how scaling SaaS requires translating technical debt into dollars, leading with values, and replacing broken performance reviews with AI-driven feedback.

What You’ll Learn:

• How firefighting shaped Stefano’s leadership style and stress management
• Why values outlast culture when scaling SaaS companies
• Lessons from migrating tens of thousands of customers off a legacy platform
• The power of decision logs for transparency and alignment
• How to frame technical debt in terms that executives understand
• Why outcome over output beats feature obsession
• How Branco.ai is pioneering continuous AI-driven feedback to replace reviews
  
  

Stefano Grossi is an executive technologist, product leader, and founder of Branco.ai, a B2B platform that uses AI-driven feedback and action plans to align company strategy with employee growth. He is also the Chief Technology & Product Officer at FreshBooks, where he has led product innovation, international expansion, and the integration of financial solutions like Stripe Connect and payroll to better serve small businesses. Previously, he scaled product development teams by 5X at SOTI, introduced Continuous Delivery and Infrastructure as Code, and increased profitability by 40%. With over 20 years in technology leadership and a background that uniquely spans firefighting, software engineering, and executive management, Stefano is known for building high-performance teams, translating technical debt into business impact, and pioneering new approaches to culture, values, and performance management in the SaaS industry.

This podcast is brought to you by Delta Systems, your one-stop shop for front-end, back-end, and full-stack software development. At Delta, Justin and Aaron share the same philosophy when it comes to clients: they treat people like colleagues, not just customers. Maybe that’s why Delta typically spends years working with the same companies: how many software engineering firms can you say that about? So, if you’ve got a big SaaS project in mind but have no idea where to start, come and get a free scope and estimate from Delta Systems on their website.

Highlights:

• [00:00] Introduction
• [01:11] From Firefighter to Technologist
• [03:26] Balancing Night Shifts and Software Development
• [04:47] Why FreshBooks: Learning Culture at Scale
• [06:41] The Longest Hiring Process and Joining FreshBooks
• [08:25] Expanding to Europe Without Losing Culture
• [10:07] Values vs. Culture: The Cornerstones of Scale
• [13:49] The Challenges of Legacy Platform Migration
• [16:22] Decision Logs, Transparency, and Communication
• [22:14] Technical Debt and the Pyramid of Needs
• [26:49] Fail Fast vs. Outcome Over Output
• [30:31] Why Stefano Founded Branco.ai
• [36:34] AI-Driven Continuous Feedback in Practice
• [42:30] What’s Next for Branco.ai

Episode Resources:

• Branco.ai Website
• Branco.ai Blog (Contains tools to support professional growth)
• Stefano Grossi on LinkedIn
• FreshBooks Website
• “The Pyramid of Needs: Selling Technical Debt to the Board” Article by Stefano
• Aaron Marchbanks on LinkedIn
• Justin Edwards on LinkedIn
• Delta Systems Website

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