Fractional CTO- Chicago

Fractional Chief Technology Officer (CTO) Part-Time / Fractional | 10–30 Hours Per Week | Remote About Performacentric Performacentric is an AI software company focused on building agentic AI solutions that help small and mid-market businesses improve operational performance, business visibility, employee productivity, and customer outcomes. We develop intelligent AI copilots and agents that automate workflows, unify fragmented business systems, and enable smarter decision-making for growing organizations. We are seeking a highly technical and execution-focused Fractional CTO to help architect, secure, scale, and operationalize our technology ecosystem. Position Overview The Fractional CTO will serve as the senior technical leader for Performacentric, guiding the company's infrastructure, development standards, cloud architecture, DevOps strategy, and long-term technical roadmap. This is a hands-on leadership role ideal for a builder who is comfortable operating both strategically and tactically. The ideal candidate can establish engineering best practices while also implementing CI/CD pipelines, managing cloud infrastructure, supporting SaaS deployments, and maintaining critical business systems such as IceWarp. The role is expected to average between 10–30 hours per week depending on active projects and operational needs. Key Responsibilities Technical Leadership & Strategy Define and execute the company's technical roadmap Recommend scalable architecture decisions for AI applications and SaaS platforms Establish software engineering standards, governance, and best practices Advise leadership on infrastructure, security, compliance, scalability, and technical investments Evaluate and recommend tools, frameworks, hosting environments, and integrations Assist with technical hiring and vendor evaluation when necessary DevOps & Infrastructure Management Design, build, and maintain CI/CD pipelines for application deployment Implement automated deployment, testing, monitoring, and rollback strategies Manage cloud infrastructure environments (AWS preferred) Configure and maintain infrastructure-as-code practices where appropriate Monitor uptime, system reliability, backups, disaster recovery, and performance optimization Establish observability and monitoring tools for infrastructure and applications Cloud & Systems Administration Manage and maintain Performacentric's cloud-hosted instance of IceWarp Handle email server administration, DNS, SPF, DKIM, DMARC, and mail security configurations Maintain user access controls, permissions, and security standards Ensure business continuity and infrastructure resilience Security & Compliance Implement cybersecurity best practices across applications and infrastructure Conduct security reviews and vulnerability mitigation Establish secure authentication and credential management practices Ensure environments follow appropriate data privacy and security standards Product & Engineering Collaboration Work alongside developers, contractors, and AI engineers to guide implementation Review application architecture and deployment workflows Help translate business objectives into technical execution plans Assist with product scalability planning as the company grows Required Qualifications 7+ years of experience in software engineering, cloud infrastructure, DevOps, or technical leadership Prior experience serving as a CTO, Head of Engineering, Lead Architect, or senior DevOps leader Strong hands-on experience building CI/CD pipelines Deep experience with AWS or similar cloud platforms Experience managing Linux-based infrastructure and cloud-hosted applications Familiarity with containerization technologies such as Docker Experience with Git-based deployment workflows and automation tools Knowledge of cybersecurity, infrastructure hardening, and access management Experience administering business communication platforms or mail infrastructure Strong written and verbal communication skills Ability to operate independently in a startup environment Preferred Qualifications Experience working with AI platforms, LLM-based applications, or automation systems Familiarity with tools such as: GitHub Actions Jenkins Terraform Kubernetes Supabase PostgreSQL N8N LangChain Vector databases Experience supporting SaaS startups or early-stage technology companies Knowledge of API architecture and integrations Familiarity with IceWarp administration Ideal Candidate Traits Builder mentality with strong execution skills Comfortable balancing strategy with hands-on implementation Able to prioritize effectively in a fast-moving startup environment Highly organized and security conscious Strong problem-solving and troubleshooting capabilities Comfortable working asynchronously and remotely Compensation Flexible hourly or monthly retainer structure ranging from $200/hr-$300/hr depending on experience and availability Long-term opportunity with growth potential as Performacentric expands Flexible remote work environment Work Schedule Fully remote 10–30 hours per week Flexible scheduling with occasional availability for leadership and technical planning meetings To Apply Please submit: Resume and cover letter Brief summary of relevant DevOps/cloud infrastructure experience Examples of CI/CD pipelines or infrastructure environments you have managed Technologies and cloud platforms you are most comfortable with Desired hourly rate or monthly retainer expectations