Oowlish is seeking a Fractional CTO to define technical architecture, guide engineering teams, and integrate AI in product strategy across startups, focusing on impactful leadership and collaboration.
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
Top Skills
AI
Cloud
Distributed Systems
Similar Jobs
Fintech • Real Estate • PropTech
Conduct outbound prospecting (cold calling, email, LinkedIn) and engage inbound leads to generate qualified opportunities. Qualify and hand off meetings to sales, join discovery meetings, and participate in ongoing coaching to refine sales development skills. Maintain organized, data-informed pipeline management aligned to ICP.
.png)
Artificial Intelligence • Healthtech • Machine Learning • Natural Language Processing • Software • Generative AI
Lead the Machine Learning Engineering team at AKASA, focusing on improving ML capabilities, model deployment, and infrastructure development, while managing and mentoring engineers.
Top Skills:
KubernetesPythonPyTorch
Digital Media • Gaming • Information Technology • Software • Sports • Esports • Big Data Analytics
As a Senior CRM Associate, you'll manage marketing campaigns, create Spanish content, analyze performance, and work cross-functionally while ensuring culturally relevant messaging.
Top Skills:
A/B TestingAnalytics ToolsHTML
What you need to know about the Boston Tech Scene
Boston is a powerhouse for technology innovation thanks to world-class research universities like MIT and Harvard and a robust pipeline of venture capital investment. Host to the first telephone call and one of the first general-purpose computers ever put into use, Boston is now a hub for biotechnology, robotics and artificial intelligence — though it’s also home to several B2B software giants. So it’s no surprise that the city consistently ranks among the greatest startup ecosystems in the world.
Key Facts About Boston Tech
- Number of Tech Workers: 269,000; 9.4% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: Thermo Fisher Scientific, Toast, Klaviyo, HubSpot, DraftKings
- Key Industries: Artificial intelligence, biotechnology, robotics, software, aerospace
- Funding Landscape: $15.7 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Summit Partners, Volition Capital, Bain Capital Ventures, MassVentures, Highland Capital Partners
- Research Centers and Universities: MIT, Harvard University, Boston College, Tufts University, Boston University, Northeastern University, Smithsonian Astrophysical Observatory, National Bureau of Economic Research, Broad Institute, Lowell Center for Space Science & Technology, National Emerging Infectious Diseases Laboratories
