Fractional CTO- Chicago

Performacentric
Chicago, IL

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
Posted 2026-05-08

Recommended Jobs

Speech Therapist - Home Health

Reliable Home Care Providers, Inc.
Chicago, IL

Job Description Job Description Description: We are looking for a part-time speech therapist to join our team! Job Description: Speech Language Pathologist in Home Health We are seekin…

View Details
Posted 2026-03-27

MECHANICAL ENGINEER

Belcan
Mossville, IL

Job Title: Mechanical Engineer Location: Mossville, IL Zip Code: 61552 Duration: 24 Months Pay Rate: $37.76/hr. Keyword's: #Mossvillejobs; #MechanicalEngineerjobs; Start Date: Immediate We pr…

View Details
Posted 2026-06-18

Principal Engineer

Relativity
Illinois

Posting Type Remote/Hybrid Job Overview ABOUT THE ROLE We’re seeking a seasoned technical leader with deep expertise in building and scaling complex, cloud-native distributed systems.…

View Details
Posted 2026-06-21

Registered Nurse- Elmhurst ED Transition Program - July 2026

Confidential
Elmhurst, IL

Hourly Pay Range: $36.00 - $55.80 - The hourly pay rate offered is determined by a candidate's expertise and years of experience, among other factors. Registered Nurse- Transition to Practice-Em…

View Details
Posted 2026-06-06

Prep Cook

J. Alexander's Restaurants
Oak Brook, IL

Job Description Job Description PREP COOK J. Alexander's Restaurant is a contemporary American restaurant, known for its daily scratch-made wood-fired cuisine. We strive to provide the …

View Details
Posted 2026-06-20

Senior Campaign Manager

SuperAwesome
Chicago, IL

SuperAwesome is an award-winning technology company that powers the youth digital ecosystem, helping brands to meet their audience where they are. We bring together proprietary advertising and gam…

View Details
Posted 2026-06-03

Field Service Technician

Biro of Chicago, Inc
Chicago, IL

Service Technician – Biro of Chicago Inc. If you’re the kind of technician who likes getting your hands on real equipment, solving real problems, and being trusted as the expert on-site, this ro…

View Details
Posted 2026-02-26

Travel Nurse RN - Orthopedics - $1,864 to $2,153 per week in Urbana, IL

TravelNurseSource
Urbana, IL

Registered Nurse (RN) | Orthopedics Location: Urbana, IL Agency: National Staffing Solutions Pay: $1,864 to $2,153 per week Shift Information: Days - 3 days x 12 hours Contract…

View Details
Posted 2026-05-21

Asst Nurse Manager Emergency

AdventHealth
La Grange, IL

Our promise to you: Joining UChicago Medicine AdventHealth is about being part of something bigger. It’s about belonging to a community that believes in the wholeness of each person, and serves to up…

View Details
Posted 2026-06-14

OTR Dry Van Company Driver W2 Job in Aurora, IL by American Trucking Group

American Trucking Group
Aurora, IL

Requirements ~3 months tractor trailer experience in 3 years ~No clearinghouse violations ~No more than 2 moving violatio…

View Details
Posted 2026-04-28