Executive Contractor Developer Jobs in Itasca, IL

Position Overview - Part-Time / Fractional Executive Contractor (15–20 hours/week) - Hybrid

The Fractional COO will partner directly with the President & CEO as the true operational co-pilot, taking ownership of day-to-day business operations so the CEO can focus on strategic growth and high-level client relationships. In this role, you will effectively run internal operations, drive operational scalability, optimize gross margins, and build the repeatable delivery engine required to scale our MSP to the next level.

Key Responsibilities & Deliverables

• Operational Leadership & Execution: Serve as the second-in-command to run day-to-day internal business functions, orchestrating cross-functional execution across service delivery, account management, and client onboarding.

• Scaling & Growth Infrastructure: Design and execute a scalable operational roadmap; eliminate delivery bottlenecks, build scalable service tiers, and ensure client capacity scales seamlessly without ballooning overhead.

• Team Accountability & Cadence: Establish and lead weekly operational leadership reviews (L10/EOS-style), setting measurable quarterly goals (OKRs/Rocks) and holding departmental heads, engineers, and account executives strictly accountable to outcomes.

• Financial & Margin Optimization: Partner with executive leadership to evaluate recurring revenue profitability, technician billable utilization, client contribution margins, and contract renewals to maximize EBITDA.

• Process Engineering & Operational Rigor: Institutionalize standardized Standard Operating Procedures (SOPs) across PSA/RMM workflows, ticket triage, client onboarding, project delivery, and escalation pathways.

• Client Retention & Service Quality: Oversee service delivery metrics (CSAT, First-Contact Resolution, SLA adherence, and churn) to ensure exceptional client satisfaction as the firm expands its client roster.

• Executive Decision-Making & Succession: Act as a thought partner and proxy for the CEO in operational decision-making, vendor management, and internal resource allocation.

Qualifications & Requirements:

Details / Specifics:

MSP Executive Experience:

• Must have 5+ years of operational leadership within an MSP or Managed IT Services firm (COO, VP of Operations, or General Manager). Direct familiarity with MSP business models, PSA/RMM platforms, and SLA management is mandatory.

• Growth & Scaling Track Record

Demonstrated success scaling an IT services company or business unit through repeatable processes, margin expansion, and structured operational frameworks (e.g., EOS/Integrator, TruMethods, Service Leadership).

• Hands-On Leadership

Proven ability to command operational respect, mentor technical teams, hold client-facing staff accountable, and manage executive reporting.

• Financial Acumen

Deep understanding of MSP unit economics: effective hourly rate (EHR), technician utilization, gross profit margins on managed agreements, and labor cost controls.

Compensation

• Compensation: Negotiable based on experience, with performance-based rate increases tied to key milestones and performance goals.

• Growth: Includes performance-based pay bumps upon reaching target goals, with a path to a permanent, full-time role.

• Pay & Progression: Flexible rate tailored to individual background, featuring structured milestone increases and opportunity for full-time transition.

Why Partner with ITRegulators, Inc.?

• Direct Growth Impact: You will have the mandate and autonomy to shape our operating model and actively steer the company's trajectory.

• High-Leverage Engagement: A strategic, structured fractional commitment focused on driving tangible results and operational maturity.

How to Apply

Submit your resume and an introductory summary detailing:

1. The MSP operational frameworks (e.g., EOS, TruMethods, Service Leadership) and tools (PSA/RMM) you have implemented.

2. An example of how you successfully scaled an MSP's operations or improved gross margins in a fractional or executive capacity.

About ITRegulators, Inc.

ITRegulators, Inc. is a full-service IT Support, IT Consulting, Managed IT, and IT Staffing company. We deliver "best-of-breed" IT solutions and take a highly proactive approach to keeping our clients' systems up, running, available, and secure. Learn more about us at www.itregulators.com.

ITRegulators, Inc. is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.