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A company's career page is a crucial source of truth during due diligence. The technologies listed in job postings reveal the actual tech stack. This can expose a major disconnect between an investor's thesis (e.g., modern, AI-native) and the on-the-ground reality (e.g., hiring for legacy Delphi developers).
Hiring managers often create AI-specific roles thinking it attracts experts. Instead, they should frame job descriptions around the complex problems the business needs to solve. This attracts true problem-solvers who can learn any necessary technology, rather than individuals skilled at keyword optimization.
Theoretical knowledge is now just a prerequisite, not the key to getting hired in AI. Companies demand candidates who can demonstrate practical, day-one skills in building, deploying, and maintaining real, scalable AI systems. The ability to build is the new currency.
A VC's relevance is now tied to their hands-on experience with modern tools. Limited Partners should add a new question to their due diligence: 'What have you built with CloudCode recently?' A lack of practical application is a red flag, indicating the VC may be out of touch with today's builders.
For technical hires, the quality of the codebase is a major selling point. A clean, well-maintained system attracts picky, high-caliber engineers who value craftsmanship, making it a powerful and often overlooked recruiting asset.
Investor Mala Gaonkar asserts that to deliver quality at scale, any business, whether in aerospace or medtech, must have a strong technology backbone. Her firm gains an edge by analyzing the "tech stack map" of companies, especially those not traditionally considered technology businesses.
A key indicator that you're working on a truly innovative frontier is when there are no recruiters, agencies, or even established job titles for the roles you need to hire. This scarcity signifies that the field is too new to have a formalized talent pipeline.
Tech due diligence is no longer a post-LOI, checkbox "IT audit." In the AI era, it has "shifted left" to become a critical, pre-LOI analysis of a company's strategic defensibility, AI maturity, and ability to innovate, often starting with outside-in signal gathering.
Many "AI Product Manager" jobs are standard PM roles with "AI" sprinkled in. A simple test is to replace every instance of "AI" with a random noun like "marble." If the description still largely makes sense or becomes nonsensical, it reveals the role lacks true AI-specific responsibilities.
When a founder or CTO builds an entire custom tech stack—including their own programming language and compiler—it's a massive red flag. This creates an unmanageable key-person risk, makes hiring impossible, and signals a mindset resistant to collaboration or external validation.
The career value of working at a big-name tech company is diminishing. Recruiters now prioritize candidates with current, AI-native skills over those with prestigious but potentially outdated experience. Your ability to demonstrate modern practices outweighs the brand recognition of your past employers.