CTO | vCTO | Chief Technology Officer - WFH & Flexible - Geylang

placeGeylang scheduleFull-time calendar_month24/7/25

We’re hiring a strategic and hands-on CTO to join our on-demand leadership pool. In this role, you’ll guide early-stage and scaling businesses through technology strategy, architecture planning, and product delivery execution. This is a flexible and part-time engagement.

This is an ideal side role for experienced tech leaders who want to apply their skills across multiple businesses and it is flexible, impactful, and financially rewarding.

Key Responsibilities

Technology Strategy & Conceptual Architecture

Define scalable, modular technology blueprints that support platform thinking and growth.
Guide tech investments across funding stages, product phases, and market shifts.

AI Integration & Agentic Systems

Identify AI-native opportunities and design agentic systems to automate and scale decisions.
Govern LLM, GenAI, and data pipeline usage with a focus on ethics, privacy, and security.

DevOps, Cloud & Engineering Maturity

Modernize CI/CD, observability, and DevSecOps practices to reduce time-to-market.
Optimize infrastructure with cost-aware cloud engineering and performance tuning.

Product & Roadmap Ownership

Align product delivery with outcomes using lean sprints, feedback loops, and velocity tracking.
Guide prioritization, MVP scope, and tech debt tradeoffs with executive clarity.

Tech Talent & Culture Development

Coach tech leads, refine team structures, and embed scalable decision frameworks.
Create a culture of engineering excellence and innovation readiness.

AI Cost & Tooling Governance

Right-size AI and cloud tooling for scale, security, and budget.
Integrate FinOps strategies and platform benchmarking to manage innovation cost-effectively.

Requirements

10+ years in software architecture, platform engineering, or product leadership.
Proven experience leading AI adoption, DevOps, and digital scaling in startup or growth-stage firms.
Deep expertise in cloud-native architecture, LLM integration, and agile leadership.
Past CTO or technical founder experience preferred.
Flexible engagement availability as fractional CTO or strategic technology advisor.

Engagement Benefits

Lead multiple high-impact projects without full-time commitment
Monthly recurring income across client engagements
Potential to earn more depending on engagement scope
Mostly remote and flexible, work from anywhere
Join expert-only C-level events and advisory circles
Perfect side role if you have bandwidth beyond your day job

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