Director of Operations

Posted 2 Days Ago
Be an Early Applicant
Woodstock, IL, USA
Hybrid
115K-120K Annually
Entry level
Cloud • Hardware • Information Technology • Software • Database • Cybersecurity • Data Privacy
Chicago's Most Trusted Managed IT Services Partner – Join a Team That Actually Cares Own IT With Us at LeadingIT!
The Role
Leads operations for an IT managed service provider, overseeing service delivery, operational margins, processes, documentation, staff development, training, budgets, performance metrics, and team accountability. The role participates in company leadership, builds scalable operational standards, drives continuous improvement, and executes short- and long-term business roadmaps. Prior IT MSP experience is required, along with strong leadership, mentoring, customer service or technical operations experience, and a results-focused mindset.
Summary Generated by Built In
Description

DIRECTOR OF OPERATIONS 

Are you a decisive, action-oriented leader who thrives in a high-growth, fast-paced environment? Do you have a relentless drive to improve, problem-solve, and execute? Our growing Managed Service Provider (MSP) is looking for a Director of Operations - someone who brings energy, confidence, and a focus on results over excuses. 

As a key member of our Leadership Team, you’ll play a critical role in shaping the company’s direction, ensuring operational excellence, and leading teams to success. 

WHO YOU ARE: 

  • You Are Driven – No questions, no approval needed. You take ownership and make things happen. 
  • You Chase Excellence – You have a demand for excellence in what you do. You strive to be the best. 
  • You Are Accountable -You take extreme ownership. You hold yourself accountable and expect the same from your team. 
  • You Stay Positive – You are a problem solver. You keep a positive mindset with a solution focus. Always focused on solutions, not obstacles. 
  • You Are Humbly Confident - You can make it happen, and if not, you are able to ask for help. 
  • You Are Growth-Oriented – You constantly seek to improve, scale, and optimize. 
  • You Want Purposeful Work– You want to be part of something bigger than a job. 

ACCOUNTABILITIES 

  • LMA – Lead, Manage, Hold Team Accountable 
  • Operational Gross Margin-45% 
  • Service Delivery -Create, Achieve, and Maintain Best in class Service Delivery Metrics 
  • Operational Processes and Documentation - Responsible for creating and maintenance of all technical operational processes and documentation 
  • Operational Staff + Development Training- Responsible for building processes, protocols, and standards for monitoring training and development of all operational staff 

WHAT WILL BE REQUIRED: 

  • Strong leadership skills – Ability to mentor, guide, and inspire teams. 
  • Proven track record – Demonstrated ability to create and accomplish results on a 12-week → 12-month roadmap. 
  • Budget Management – Establish and operate within your Operational budget. 
  • Metrics-Driven Mindset – Define and implement measurable success benchmarks. 
  • Technical or Customer Service Leadership Experience – OR the ability to learn the industry within 90 days. 
  • Relentless Focus on Results – No excuses, no job justification—just execution. 
  • Experience working at an IT MSP is REQUIRED

WHY JOIN US? 

  • Seat at the Leadership Table – Help shape the company’s future. 
  • Fast-Paced & High-Impact Role – Be part of an organization that values agility and execution. 
  • Culture of Extreme Ownership & Excellence – No micromanagement, just high expectations. 
  • Opportunities for Growth & Leadership – Your success is our success. 
  • Ready to take full ownership, drive change, and lead teams to new heights? Apply today and be a key player in the future of IT services! 

Our all-inclusive total compensation and benefits package for this role includes:

  • Salary is based on your experience, drive and the value you can bring our company; and is in the range of $115,000 to $120,000 per year with potential to earn up to 7% of salary incentive bonuses.
  • We provide 100% company paid health, dental, life, and vision benefits – value of $4,500 to $14,000/year
  • We match 5% of your contributions to Guideline 401k – value of 5% of salary.
  • Open Door PTO policy
  • Company provided gear (notebook + softphone) as well as company clothing.

Our hiring process:

  • Submit your application
  • If we like what we see, we will reach out to schedule a video interview

Additional Perks:

We’re building a company where success is shared. LeadingIT has committed to distributing $5 million in profit back to our team over the next 10 years—on top of fully paid benefits, unlimited PTO, and a people-first culture. We are building something that changes lives.

For a more in depth look at our jobs/benefits/hiring timeline check out www.goleadingit.com/careers

Skills Required

  • Strong leadership skills, including the ability to mentor, guide, and inspire teams
  • Proven track record of creating and accomplishing results on a 12-week to 12-month roadmap
  • Ability to establish and operate within an operational budget
  • Metrics-driven mindset and ability to define and implement measurable success benchmarks
  • Technical or customer service leadership experience, or ability to learn the industry within 90 days
  • Experience working at an IT managed service provider
  • Relentless focus on results and execution
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The Company
HQ: Woodstock, IL
38 Employees
Year Founded: 2010

What We Do

We cybersecure your organization. LeadingIT provides fast+friendly cybersecurity and technology (unlimited) support for nonprofits, manufacturers, schools, accounting firms, religious organizations, government, and law offices with 10-200 employees across the Chicagoland area.

Why Work With Us

Own your career with a team that owns every challenge. We're a 15-year Chicago MSP recognized as Inc. 5000 & MSP 501, with 98% customer satisfaction. Join 35+ problem-solvers making real local impact. You'll get mentorship, development support, EOS structure, promotion from within, and a crew that has your back.

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