Fractional CTO (Startup & AI-Driven Teams)

Oowlish

New York, United States Remote permanent

Posted: March 10, 2026

Job Description

Join Our Team

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.

About the role:

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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