The recent trend of founder-CEOs returning to lead their companies, like at Workday, isn't about general management. It signals a crisis where the core product roadmap needs a fundamental AI-driven reinvention, a task that requires the founder's specific, deep historical knowledge.
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According to Techstars' CEO David Cohen, standout AI companies are defined by their leadership. The CEO must personally embody an "AI-first" mindset, constantly thinking about leverage and efficiency from day one. It's not enough to simply lead a team of engineers who understand AI; the strategic vision must originate from the top.
For incumbent software companies, surviving the AI era requires more than superficial changes. They must aggressively reimagine their core product with AI—not just add chatbots—and overhaul back-end operations to match the efficiency of AI-native firms. It's a fundamental "adapt or die" moment.
While technical founders excel at finding an initial AI product wedge, domain-expert founders may be better positioned for long-term success. Their deep industry knowledge provides an intuitive roadmap for the company's "second act": expanding the product, aligning ecosystem incentives, and building defensibility beyond the initial tool.
Successor CEOs cannot replicate the founder's all-encompassing "working memory" of the company and its products. Recognizing this is key. The role must shift from knowing everything to building a cohesive team and focusing on the few strategic decisions only the CEO can make.
Enterprise surveys show a major shift: CEOs are taking direct control of AI initiatives from CIOs. They are increasingly willing to make substantial, long-term investments in AI—even if a recession hits or if tangible ROI isn't immediately measurable—viewing it as an existential imperative for survival and growth.
Brian Halligan, HubSpot's longtime CEO, observes that the established rules for corporate leadership are obsolete. He cites unconventional leaders like Elon Musk, Nvidia's Jensen Huang (with 60 direct reports), and Airbnb's Brian Chesky as examples of innovators who are successfully rethinking company management from scratch.
To avoid complacency, Miro's CEO asks himself daily, "If I started this company today, what would the product and strategy look like?" The answer to this question determines whether the company needs a small evolution or a complete strategic rebuild to stay relevant in the market.
Workday's CEO change reflects a broader trend: the belief that founder-technologists are essential for navigating the AI transition. Similar to leaders who guided cloud migrations at Microsoft and Adobe, these founders are being brought back to ensure companies invest correctly and 'cross the chasm' in a post-AI world.
Founders remain long after hired executives depart, inheriting the outcomes of past choices. This long-term ownership is a powerful justification for founders to stay deeply involved in key decisions, trusting their unique context over an expert's resume.
During major tech shifts like AI, founder-led growth-stage companies hold a unique advantage. They possess the resources, customer relationships, and product-market fit that new startups lack, while retaining the agility and founder-driven vision that large incumbents have often lost. This combination makes them the most likely winners in emerging AI-native markets.
