Fractional CTO (Startup & AI-Driven Teams)

Oowlish, one of Latin America's rapidly expanding software development companies, is seeking experienced technology professionals to enhance our diverse and vibrant team.

As a valued member of Oowlish, you will collaborate with premier clients from the United States and Europe, contributing to pioneering digital solutions. Our commitment to creating a nurturing work environment is recognized by our certification as a Great Place to Work, where you will have opportunities for professional development, growth, and a chance to make a significant international impact.

We offer the convenience of remote work, allowing you to craft a work-life balance that suits your personal and professional needs. We're looking for candidates who are passionate about technology, proficient in English, and excited to engage in remote collaboration for a worldwide presence.

Many early-stage and growth companies need senior technical leadership, but not always on a full-time basis.

They need experienced leaders who can:

• Define technical architecture that scales with the company

• Align product vision with engineering execution

• Guide engineering teams through growth and complexity

• Introduce discipline without slowing momentum

• Use AI as a force multiplier across the development lifecycle

This is not a ceremonial CTO role.

This is hands-on strategic leadership with real influence across high-potential startups.

We are connecting with leaders who want to operate across multiple ventures, while partnering with a strong engineering organization capable of executing at speed.

What You Will Do:

• 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

Why This Is Different

• 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/

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