Oowlish

Fractional CTO (Startup & AI-Driven Teams)

Oowlish  •  New York (Remote)  •  2 months ago
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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/#LI-LM1#LI-CD1#LI-EA1#LI-TC1#LI-ET1#LI-TT1#LI-JH1#LI-DP1#LI-LS1#LI-AB1#LI-KN1#LI-SR1#LI-JS1#LI-FZ1
Oowlish

About Oowlish

We are on a mission to give every company, no matter the size, the opportunity to innovate and help build a better future.

Our Services:

Dedicated Tech (full/partial) Squads: we create multi-disciplinary, remote (near-shore) Tech Squads that become part of your team. They adapt to your workflows and are trained on Agile methodologies to deliver continuous value. We believe that well-trained remote teams bring clients the opportunity to increase innovation output by accessing a greater / more diverse pool of talent, while reducing the cost of development.

On-Demand Software Development: at our core, we are software developers excited about building digital products and solutions using the latest technologies and agile methodologies. We provide end-to-end capabilities to deliver on your technical requests. Product Management, Tech Architecture, Front / Back End Development, Devops & QA

Ventures: We partner with entrepreneurs and organizations to invest and build from scratch new businesses. We co-design a desired Minimum Lovable Product to find product market fit and scale in a lean way. As startup founders ourselves, we love getting things from 0 to 1.

We are End-To-End Innovation Enablers, helping your company unlock its full innovation potential.

Industry
IT & Software
Company Size
51-200 employees
Headquarters
Work from Anywhere, BR
Year Founded
2017
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