Okay, I've searched for Chief Technology Officer roles in New York City that fit your criteria for AI and enterprise software, focusing on zero-trust security models, full technical ownership, and experience in SaaS products. I found 27 positions that match your search.

Sure. Here's the analysis:

Job Analysis:

The Chief Technology Officer (CTO) role at Olis is fundamentally about pioneering the technical architecture and driving the development of an innovative AI knowledge infrastructure aimed at enhancing enterprise operations. The core responsibilities involve designing and owning complex product architectures that integrate AI capabilities into existing enterprise systems, effectively transforming fragmented knowledge into cohesive, accessible formats. Given the pre-revenue stage of Olis, this position requires someone who can operate independently while leading the charge in technical areas such as retrieval-augmented generation (RAG) pipelines, zero-trust security systems, and custom integration solutions within enterprise SaaS ecosystems. Success in this role means not only technical adeptness but also the ability to strategically align technology with business needs, manage ambiguity, foster collaboration within a small founding team, and ultimately lay a building block for scalable enterprise operations. Candidates will face challenges such as transforming theoretical AI capabilities into practical delivery, navigating startup uncertainty, and making high-stakes decisions that affect both product and organizational culture. There is an implied expectation of achieving significant project milestones, such as developing secure cloud deployment models and building resilient systems that satisfy enterprise demands within the first 6-12 months of employment.

Company Analysis:

Olis represents an emergent force in the tech landscape, particularly in the AI domain focused on enterprise solutions. As a pioneering enterprise in AI Knowledge Infrastructure, the company operates at the intersection of cutting-edge technology and deep organizational need, positioning itself as a crucial player tackling systemic inefficiencies within large organizations. Given that Olis is pre-revenue and pre-funding, the atmosphere is likely dynamic and fast-paced, with a strong focus on innovation and foundational work, suggesting a startup culture that values agility and creativity. Collaboration will be key, especially in a small team where each member must play a decisive role in determining the company's trajectory. This place values craft and capability over formal credentials, aligning with an inclusive environment where practical tech experience holds more weight than traditional degree qualifications. The CTO will not only need technical expertise but also strategic vision to ensure that the technology roadmap aligns closely with the broader mission of delivering transformative enterprise solutions. The role is directly tied to the company’s growth potential, with expectations to architect foundational systems that can scale and adapt, truly embodying the growth-oriented mindset crucial to thriving in a startup environment.

Absolutely. Here are some mock interview questions that could come up:

• Tell me about a time when you had to lead a technical initiative from concept to deployment. What challenges did you face, and how did you overcome them?
• Can you describe your experience working with retrieval-augmented generation models? How did you implement them in previous projects?
• Give an example of a situation where you had to balance speed and durability in a technology project. How did you approach that decision?
• What strategies do you use to ensure that data security considerations are met when developing enterprise software?
• How would you approach building integrations across multiple enterprise SaaS applications like Slack and Teams?
• Describe your understanding of secure deployment models. How would you handle designing one for Olis's architecture?
• Imagine you are faced with a situation where a critical bug is discovered right before a major software release. How would you handle it?
• If you were to encounter resistance from other team members regarding a new technology integration, how would you address that?
• What are your thoughts on the role of AI in transforming enterprise operations, and how can it be best leveraged in a company like Olis?
• Why are you interested in working at Olis specifically, and how do you see your values aligning with the company’s mission?
• What excites you the most about the opportunity to build a foundational technology at a startup like Olis?
• Considering the company is pre-revenue, what strategies would you employ to mitigate risks associated with technology development?