Fractional CTO (Startup & AI-Driven Teams)
Oowlish Technology, San Francisco, CA, United States
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/
#J-18808-Ljbffr
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/
#J-18808-Ljbffr