Oowlish Technology - Fractional CTO (Startup & AI-Driven Teams)
Requirements
• Define and evolve scalable architecture from early-stage to growth • Make high-impact technical decisions under uncertainty • Partner directly with founders on product and technology strategy • Lead and mentor distributed engineering teams • Establish lean, high-velocity development processes • Integrate AI tools and workflows to increase development speed and quality • Evaluate technical debt pragmatically and prioritize what matters • Support hiring decisions and engineering organization design when needed • Experience as CTO, VP of Engineering, or senior technical leader • Track record of taking products from 0 → 1 and 1 → scale • Deep architectural experience across modern tech stacks • Strong cloud and distributed systems expertise • Comfortable operating in ambiguity • Understands capital efficiency and startup constraints • Moves fast while staying pragmatic • Focuses on impact rather than perfection • Practical experience using AI tools to accelerate development, prototyping, testing, and documentation • Understands where AI increases velocity and where engineering judgment is essential • Experience leading distributed, nearshore, or offshore engineering teams • Ability to build trust and performance across time zones • Strong communication skills with both engineers and business leaders • Focus on technical leadership and strategy, not delivery management • Operate across multiple companies and high-growth environments • Work alongside a partner that provides deep engineering execution capacity • Flexible engagement models designed around impact and outcomes
Responsibilities
• Define and evolve scalable architecture from early-stage to growth • Make high-impact technical decisions under uncertainty • Partner directly with founders on product and technology strategy • Lead and mentor distributed engineering teams • Establish lean, high-velocity development processes • Integrate AI tools and workflows to increase development speed and quality • Evaluate technical debt pragmatically and prioritize what matters • Support hiring decisions and engineering organization design when needed • Proven Technical Leadership: • Experience as CTO, VP of Engineering, or senior technical leader • Track record of taking products from 0 → 1 and 1 → scale • Deep architectural experience across modern tech stacks • Strong cloud and distributed systems expertise • Startup Execution Mindset: • Comfortable operating in ambiguity • Understands capital efficiency and startup constraints • Moves fast while staying pragmatic • Focuses on impact rather than perfection • AI-First Engineering Mindset: • Practical experience using AI tools to accelerate development, prototyping, testing, and documentation • Understands where AI increases velocity and where engineering judgment is essential • Distributed Leadership: • Experience leading distributed, nearshore, or offshore engineering teams • Ability to build trust and performance across time zones • Strong communication skills with both engineers and business leaders
Benefits
• Focus on technical leadership and strategy, not delivery management • Operate across multiple companies and high-growth environments • Work alongside a partner that provides deep engineering execution capacity • Flexible engagement models designed around impact and outcomes • Come join us in breaking the mold and revolutionizing the tech landscape! • You can also apply here: • Website: https://www.oowlish.com/work-with-us/ • LinkedIn: https://www.linkedin.com/company/oowlish/jobs/ • Instagram: https://www.instagram.com/oowlishtechnology/ • We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.
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