#414 Tech Due Diligence Mastery with Joe Conley: M&A, PropTech, and Gen AI Integration

In this episode of The CTO Show with Mehmet, we sit down with Joe Conley, an accomplished CTO and the founder of Techsight, to dive deep into the intricacies of technology leadership and innovation. With over 16 years of experience in software engineering, Joe has honed his expertise in scaling data platforms, navigating M&A due diligence, and driving efficiency for startups and established businesses alike. Currently based in the greater Philadelphia area, Joe shares his journey from full-stack engineering to fractional CTO roles, offering a unique perspective on the challenges and rewards of leading in tech. Key Topics Discussed: Technical due diligence red flags in M&A Integration challenges post-acquisition PropTech trends and data standardization Practical applications of Generative AI in business Transitioning from engineering to technical leadership Building simple, effective systems at scale Notable Quotes: "Anyone who's built a startup knows that nothing's perfect, you know, you're going to take, you're going to incur tech debt in certain areas." - Joe Conley "Having a good understanding of the business and the market that you're in... I think that's probably a good sort of general point for anyone who wants to be a CTO." - Joe Conley About Joe Conley: Joe Conley is a Fractional CTO based in the greater Philadelphia region. Through his company TechSight, he provides technical leadership for M&A due diligence, startup scaling, and enterprise technology transformation. His experience spans multiple industries including PropTech, healthcare, and telecommunications. Links and Resources: • Connect with Joe Conley on LinkedIn. • Learn more about Techsight at techsight.dev. • Check out Joe’s personal blog at jpc2.org. 00:00 Introduction and Guest Welcome 01:06 Joe Conley's Background and Career Journey 01:43 Challenges and Opportunities in Startups 02:47 Building Robust Systems Across Industries 05:41 Technical Due Diligence in M&A 15:51 Trends in PropTech and Real Estate 18:15 The Impact of Gen AI on Technology 38:25 Advice for Aspiring CTOs and Leadership Insights 44:31 Conclusion and Final Thoughts