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

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 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.

Must Have:

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.