Looking for a job

Cyrus Osawaye

@cyrusosawaye

CTO at OREE Technologies building backend architecture for an AI-powered sales platform; also developing multi-agent systems and full-stack products.

Nigeria

Message

What I'm looking for

I’m looking for senior engineering roles, technical leadership opportunities, and select freelance engagements in AI engineering and software development. I want to keep building at the intersection of AI and software, where AI systems reason and act while people stay in control of what matters.

At OREE Technologies Ltd., I lead the technical vision and backend architecture for Oree AI, an AI-powered Sales Development Representative platform built to automate and scale outbound sales pipelines. I oversee system design, infrastructure, and integrations.

As an AI Engineer at Fiverr, I developed a TikTok video automation pipeline that automated the process from topic generation to upload. I also designed AI workflows that turned structured data into short-form content and integrated APIs and no-code platforms to reduce manual work.

At ZumboX Technologies, I developed backend systems and conducted web application security assessments. My work included scalable APIs, microservices, security testing tools, and secure authentication systems.

I’m independently building Caddie, a career intelligence SaaS for Upwork freelancers that combines job scoring, client research, and AI-powered proposal generation. I work with multi-agent systems, LLM integrations, and full-stack products, and I’m open to senior engineering roles, technical leadership opportunities, and select freelance engagements.

Experience

Work history, roles, and key accomplishments

Current

Chief Technology Officer

Current

OREE Technologies Ltd

Feb 2026 - Present (9 months)

Leading the technical vision and backend architecture of Oree AI an AI-powered Sales Development Representative (SDR) platform built to automate and scale outbound sales pipelines. Overseeing system design, infrastructure, and integrations.

Current

Software Engineer

Current

Upwork

Aug 2024 - Present (2 years 3 months)

Worked as Software Engineer at Upwork.

Current

AI Engineer

Current

Fiverr

Apr 2024 - Present (2 years 7 months)

• Developed a TikTok video automation pipeline, achieving full end-to-end automation from topic generation to upload.
• Designed AI workflows that transformed structured data into engaging short-form content, enhancing client engagement.
• Integrated APIs and no-code platforms to streamline operations, significantly reducing manual tasks for clients.

Back End Developer

ZumboX Technologies

Apr 2024 - Oct 2025 (1 year 6 months)

Backend Developer & Security Specialist at ZUMBOX TECHNOLOGY
I specialize in developing secure backend systems and conducting web application security assessments. My expertise includes building scalable APIs, microservices, and custom security testing tools. I handle both development and security responsibilities - from designing robust authentication systems to performing penetration testing and