Episode Summary:

In this episode of Automate or Die Trying, host Wil Ramos sits down with Alessandro Pireno, a fractional CTO and CPO, board advisor, and AI, data, and go-to-market leader who helps early-stage startups scale. Alessandro has led product engineering and sales engineering teams at Snowflake and Surreal DB. His unique path spans applied physics, engineering, product leadership, and sales, giving him a 360-degree perspective on building, selling, and scaling technology.

Alessandro shares insights from his experience helping startups navigate technical product commercialization, particularly in the AI infrastructure space. He explains common pitfalls, including products that technically excel but fail to align with customer value or economic impact. He highlights how startups can distinguish between “nice-to-have” features versus core value drivers, emphasizing the importance of translating technical capabilities into measurable outcomes for customers.

The discussion explores the critical role of sales engineers in driving adoption, not just demos, and how cross-functional collaboration between sales and engineering teams accelerates success. Alessandro also dives into key differences between CIO and CISO perspectives, how AI has reshaped executive priorities, and why understanding the true customer pain is more valuable than superficial feature adoption.

He shares real-world examples of when beautiful UX or “pretty packaging” can mislead buyers, stressing that delivering the right solution—even if it looks less polished—creates real value and long-term trust. He also emphasizes the importance of leveraging proprietary data effectively as a competitive advantage in AI product development.

For technical leaders—CTOs, VPs of engineering, and founders building AI or data-driven products—Alessandro’s principle is clear: stress-test assumptions, focus on delivering measurable impact, and use cross-functional experience to bridge the gap between engineering, product, and sales.

Key Takeaways:

1. AI adoption alone does not guarantee differentiation; understand real customer impact
2. Translate technical features into measurable business value, not just performance metrics
3. Strong collaboration between sales engineers and sales teams accelerates adoption
4. CIOs often focus on cost optimization, while CISOs prioritize risk management
5. Proprietary data is the “crude oil” that makes AI-powered products unique
6. Avoid prioritizing aesthetics over function when delivering solutions
7. Early-stage startups benefit from fractional leadership with a cross-functional lens

Connect with Alessandro Pireno:

1. LinkedIn: https://www.linkedin.com/in/apireno
2. Website: https://pireno.com

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