Fractional CTO & Technical Leadership

Senior Technical Leadership Without Another Full-Time Executive

When your business needs someone to own difficult technical decisions and help carry them out, I can work alongside your team as a hands-on fractional CTO. Architecture, vendors, development, infrastructure, and day-to-day reliability all need to fit together.

Engagements starting around $2,500/month, with scope and working arrangements agreed before work begins.

Leadership that can get into the systems

I spent seven years as CTO of a software company. My experience grew out of programming and systems work, and I still work directly with code, infrastructure, logs, deployments, and the people responsible for keeping them running.

• Architecture and systems integration: understand dependencies and make decisions your team can implement.
• AWS and infrastructure: multi-account architecture, Linux, Docker, deployment workflows, and operational ownership.
• Teams and vendors: lead distributed developers across countries and time zones, clarify deliverables, and resolve competing explanations.
• Project management and recovery: find blockers, prioritize work, and turn stalled projects into achievable milestones.
• Security and compliance coordination: bring technical work, vendors, and evidence together, drawing on experience with PCI DSS requirements.
• Technical budgeting: review cloud and vendor costs, plan investments, and make tradeoffs visible.
• Modernization and technical debt: improve older systems while maintaining business continuity.
• Incident and problem resolution: inspect failures, coordinate recovery, and address recurring causes.

What working together looks like

• Establish the current picture: business priorities, system architecture, people, vendors, costs, and immediate risks.
• Agree on ownership: decisions I handle, work I implement, team responsibilities, and an appropriate communication cadence.
• Execute a prioritized roadmap: fix urgent problems, improve deployment and operations, and document decisions.
• Review progress: show what changed, what remains uncertain, and which decisions need your input.

I have set up and managed collaboration tools such as Slack and Jira. The tools support clear responsibilities and useful communication; they are not the outcome.

A practical starting engagement

Engagements starting around $2,500/month. The scope, priorities, and working arrangements are agreed before we start. This is a fit for small and mid-sized companies that need senior technical judgment and implementation help without hiring a full-time CTO.

Older systems and modern delivery belong in the same conversation

An operational system does not become disposable because it is old. I help teams connect legacy applications to APIs and cloud services, introduce safer deployment workflows, and reduce operational risk in manageable steps. AI and Codex can accelerate analysis, documentation, testing, and implementation; the objective is a system the business can depend on.

Legacy Systems & Integration →   Integration Rescue →   About Herb →