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
We are seeking a visionary Deputy Chief Technology Officer (CTO) to lead the transformation of engineering operations through AI-driven innovation. This role is ideal for a strategic technology leader who combines executive-level decision-making with hands-on technical depth. You will be responsible for redefining how engineering teams operate by driving the adoption of Generative AI, improving velocity, enhancing architectural governance, and elevating overall software delivery quality.
This position requires someone who has successfully led large-scale engineering modernization initiatives, built world-class technical organizations, and partnered closely with executive stakeholders to demonstrate the ROI of technical investments. You will act as a connector between engineering, architecture, product, sales, and customer teams—ensuring that technical excellence directly supports business outcomes. If you thrive at the intersection of engineering leadership, AI strategy, and organizational scaling, this role provides an opportunity to shape the future of high-performance software delivery.
Responsibilities:
- AI-Driven Development Transformation
- Lead AI adoption across engineering to accelerate SDLC and remove repetitive tasks.
- Define KPIs to measure AI impact (velocity, quality, debt reduction, ROI).
- Build secure governance frameworks for enterprise AI usage (privacy, IP, compliance).
- Technical Architecture & Innovation
- Oversee architectural direction for scalable, resilient platforms.
- Modernize infrastructure and cloud strategy to support advanced AI workflows.
- Mentor senior engineers and architects to elevate technical execution.
- Organizational Leadership & Scaling
- Build and scale high-performing engineering teams.
- Implement AI-native workflows for hiring, onboarding, and team management.
- Foster a culture of experimentation with accountability and high delivery standards.
- Commercial & Client Strategy
- Represent technology leadership in client meetings and strategic presentations.
- Partner with Sales/Product to highlight competitive advantages of AI-enabled engineering.
- Ensure AI solutions meet diverse compliance, security, and regulatory requirements.
Must Have:
- 5+ years in senior engineering leadership roles (VP Eng, CTO, Deputy CTO).
- Proven track record leading AI-driven transformation initiatives.
- Experience implementing Generative AI (LLMs, code gen, automated testing, documentation).
- Strong ability to quantify ROI from technical improvements and present to executives.
- Deep knowledge of governance, security, and risk management for enterprise AI usage.
- Hands-on expertise with modern technologies (.NET, Python, React/React Native, Angular, Next.js, TypeScript, etc.).
- Strong background in cloud architecture (AWS, Azure, or GCP).
- Exceptional communication skills for translating technical concepts to non-technical stakeholders.
- Full fluency in English (required).
Nice to Have:
- Fluency in Spanish and/or Portuguese.
- Experience guiding distributed or international engineering teams.
- Background working with highly regulated industries.
- Experience combining AI strategy with client-facing responsibilities.
Benefits & Perks:
- Home office
- Competitive compensation based on experience
- Career plans to allow for extensive growth in the company
- International Projects
- Oowlish English Program (Technical and Conversational)
- Oowlish Fitness with Total Pass
- Games and Competitions
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/