Sam Schillace

Sam Schillace builds applications that combine AI models with conventional software. Microsoft's CVP and deputy CTO in March 2024, he was leading a prototyping team in the CTO's office by October 2025, exploring human–AI collaboration through reasoning, memory and context awareness. He is also one of the creators of Writely, which became Google Docs following Google's acquisition.[1][2]

Schillace joined Microsoft in 2021, saying he saw it becoming an “open-minded, more energetic, startup-y place.” His criterion for AI usefulness is the work it saves people: in an October 2025 profile, he said, “It’s cool if it does neat tricks,” but “it doesn’t matter if the human is still spending just as much time getting the work done.”[2]

Schillace recalled receiving early GPT-4 access around September 2022. He interpreted it as a shift from computing through syntax, schemas and programming languages toward working with meaning and intention. He built Semantic Kernel with a small team to bring code and model inference together, describing it as a pipelined orchestrator in which one step's output could feed the next.[1]

One experiment helped produce his advice to break difficult tasks into pieces. GPT-4 could reason its way to the answer to a historical question—the year 2000—but Schillace could not prompt it to return only that year. He instead passed its explanatory output to a second prompt that extracted the answer. In his March 2024 account, he reported perfect accuracy for that extraction experiment; the account supplies no sample size or evaluation protocol.[1]

Schillace wrote the principles known as the Schillace Laws, crediting a designer on his team with attaching his name and publishing them. He treated them as provisional engineering judgments. In March 2024, he questioned whether his earlier principle that text was the universal wire protocol would survive advances in multimodality, noting that those capabilities had not been available when he wrote it.[1]

Schillace's internal experiments included the “infinite chatbot,” a retrieval-augmented bot project he described as Semantic Kernel's successor, followed by multi-agent autonomy work. He reported agents getting caught in feedback loops, repeatedly complimenting each other or generating responses about frustration and going “on strike.” His resulting recommendation was to encode the larger process in code and let models fill in bounded pieces: “Think with the model, plan with code.”[1]

His textbook factory, described in March 2024 as a project from the previous year, illustrated that division. Schillace said it used roughly 200 lines of Python in a Jupyter notebook and six short prompts. A request supplied a subject and grade level; the workflow then generated a curriculum, chapters, lessons, lesson plans, a teacher's guide and a table of contents through about a thousand API calls. He called it reliable at producing textbooks but brittle outside that domain: it would not produce a cookbook or novel. That reliability concerned completing the prescribed output, rather than demonstrating factual or educational quality.[1]

Schillace urged technical leaders to build with AI and encounter its failures directly. His own leadership involved exchanging ideas with engineers and designers; he said he generally avoided touching his team's code because coding could absorb all his attention. His advice in the 2024 interview was concrete: “Like, you have to like build stuff. Like, break your nose on stuff and like figure out what doesn't work.”[1]

Before his Microsoft AI work, Schillace helped build collaborative document editing in the browser. His earlier Writely work provides a concrete example of engineering around the limits of an emerging platform.[1][3]

Schillace, Steve Newman and Claudia Carpenter founded Upstartle, the company behind Writely's collaborative document editor. Google acquired the company in March 2006, and Writely became the basis of Google Docs.[3][2]

Schillace recalled building early Writely before browsers had capable JavaScript virtual machines. Execution limits made character-by-character searches impractical when computing changes to document text, so he used binary searches at both ends of the string diff. The example captures a specific technical decision required to make browser-based editing work under those constraints.[1]

In March 2024, Schillace said his personal Google Docs account still held the first document, originally used with Newman to test collaboration. He also noted that both the frontend and backend had each been rewritten at least twice to his knowledge, making its continuity more a matter of the surviving document than the original software.[1]