Deputy Chief Technology Officer (CTO) – AI & Engineering Strategy

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.

We are looking for a visionary Deputy CTO with deep experience transforming engineering processes through the strategic use of Artificial Intelligence (AI). The ideal candidate is a hands-on leader who has successfully guided development teams toward higher velocity, quality, and operational excellence by introducing and optimizing AI-powered practices.

In this role, you will help us refine, elevate, and scale our existing engineering processes, strengthening the connection between architectural governance, team growth, and customer-facing technical leadership.

AI-Driven Development Transformation:

• Accelerate SDLC: Lead the adoption of Generative AI tools and coding assistants to reduce cycle times and eliminate repetitive engineering tasks drastically.
• Measure Impact: Define and track KPIs related to AI adoption (e.g., velocity increase, code quality metrics, reduction in technical debt) to prove ROI.
• AI Governance & Ethics: Establish a secure framework for using AI tools within the company, ensuring strict adherence to data privacy, IP protection, and security compliance standards.

Technical Architecture & Innovation:

• Architectural Oversight: Design and oversee the roadmap for complex, scalable platforms, ensuring they are built for resilience and future growth.
• Tech Stack Modernization: Continuously evaluate and optimize our infrastructure and cloud strategy to support high-performance AI integration.
• Mentorship: Provide high-level technical guidance to Principal Engineers and Architects, resolving complex blockers and fostering technical excellence.

Organizational Leadership & Scaling:

• Team Building: Build and structure high-performing engineering teams from the ground up, optimizing for agility and cross-functional collaboration.
• Process Optimization: Implement "AI-native" workflows that redefine how we hire, onboard, and manage engineering talent for maximum output.
• Culture of Innovation: Foster an environment where experimentation is encouraged, but accountability and delivery are paramount.

Commercial & Client Strategy:

• Serve as the primary technical voice in high-stakes client meetings, simplifying complex architectural concepts into compelling business value propositions.
• Business Growth: Partner with Sales and Product teams to articulate the competitive advantage of our AI-enabled development processes to prospective clients and investors.
• Client Solution Viability & Compliance: Ensure the flexibility and compliance of AI adoption strategies (governance, tools, data privacy) to meet the diverse security and regulatory requirements of our clients.

We offer the convenience of remote work, allowing you to craft a work-life balance that suits your personal and professional needs.

• Senior Leadership Experience: 5+ years in a senior technology role (VP of Engineering, CTO, or Deputy CTO) with a focus on software delivery.
• AI Implementation Track Record: Demonstrable experience leading the transformation of engineering teams through Generative AI (e.g., LLMs for code generation, automated testing suites, and documentation).
• Proven ROI Analysis: Expertise in quantifying the efficiency gains derived from technical initiatives and reporting these to executive stakeholders.
• Governance Expertise: Strong understanding of security risks and governance associated with using third-party AI tools in an enterprise environment.
• Communication Skills: Exceptional ability to bridge the gap between technical complexity and business strategy for non-technical audiences.
• Modern Tech Stack Expertise: Hands-on experience working with several modern technologies such as .NET, Python, React/React Native, Angular, Next.js, TypeScript, among others. This includes the ability to guide teams across diverse frameworks, evaluate technological trade-offs, and define best practices across frontend, backend, and full-stack development.
• Infrastructure Background: Deep experience in large-scale system architecture and cloud ecosystems (AWS, Azure, or GCP).
• Language Skills: Full fluency in English (required). Fluency in Spanish and/or Portuguese is considered a strong plus.