Chief Operating Officer

Heartland Computers • McHenry, IL

2d • Hybrid

About The Position

Heartland is a growing technology solutions provider serving commercial and enterprise customers with technology products, managed services, and professional services. The Chief Operating Officer is an executive leadership role and the CEO’s operating partner, responsible for translating strategy into disciplined execution, profitable growth, and measurable results. The COO reports to the CEO and leads Operations and Finance, establishing the processes, systems, and accountability needed to scale the company’s solutions and services businesses. This is a hands-on, collaborative role suited to a local candidate with relevant leadership experience at a value-added reseller (VAR), managed services provider (MSP), or comparable IT solutions company.

The COO will lead operating execution and accountability; Finance and Accounting; product operations; managed, network, and professional services delivery; working capital and vendor economics; scalable systems and processes; and leadership and team development. Success in the first year includes reliable financial reporting and forecasting, clear visibility into product and services profitability, stronger cash conversion, consistent order-to-cash and procure-to-pay processes, systematic capture of vendor economics, and measurable improvements in service delivery and utilization. The COO will establish an accountable leadership cadence and an operating model that supports continued growth.

The position is based in McHenry, Illinois, with a combination of hybrid and onsite work. Candidates should live within commuting distance; relocation assistance is not available. Base salary is $180,000–$225,000, depending on experience and qualifications, with eligibility for a competitive quarterly incentive opportunity.

Requirements

• 10+ years of progressive leadership experience, including significant responsibility for operations and financial performance within a VAR, technology reseller, distributor, or comparable product-centric IT solutions company.
• Demonstrated budgeting, forecasting, gross-margin management, working-capital, and cash-flow experience, with a track record of improving profitability and operating performance.
• Practical knowledge of hardware and software resale, procurement, fulfillment, manufacturer programs, distribution relationships, rebates, and special pricing.
• Success improving systems, data quality, and cross-functional processes.
• Hands-on, collaborative leadership, strong analytical judgment, clear communication, and the ability to develop leaders, hold teams accountable, and execute in an entrepreneurial environment.
• Must be local and able to commute to McHenry, Illinois.
• A bachelor's degree in business, finance, accounting, or a related field is preferred.

Nice To Haves

• Experience leading managed or professional services operations is highly valued.
• An MBA, CPA, or equivalent financial experience is beneficial but not required.

Responsibilities

• Partner with the CEO and executive team to translate strategy into operating plans, financial goals, and clear ownership.
• Establish a regular operating cadence using KPIs, performance reviews, and follow-through.
• Lead Finance and Accounting, including reporting, budgeting, forecasting, internal controls, and coordination with banking, tax, and audit partners.
• Provide timely visibility into gross profit, EBITDA, cash flow, and profitability by customer, service, and business line.
• Help evaluate investments and strategic opportunities.
• Own the operating flow from customer order through procurement, fulfillment, invoicing, and collection.
• Improve inventory management, returns, credits, and transaction accuracy.
• Partner with Sales leadership on pricing, deal review, and processes that support growth and protect margins.
• Lead operational performance across AlwaysOn managed services, AlwaysConnected network services, and professional services.
• Improve service quality, customer experience, resource planning, utilization, and delivery consistency.
• Establish reliable time tracking, service costing, and reporting to support profitable growth.
• Improve DSO, cash forecasting, customer credit, inventory, and payment terms.
• Strengthen manufacturer and distributor relationships and ensure rebates, incentives, special pricing, market-development funds, and credits are tracked, captured, and reflected in profitability.
• Oversee improvements to ERP, CRM, financial, and service-management platforms.
• Automate manual work, improve data accuracy, and build dashboards that help leaders make decisions.
• Create processes that support growth without unnecessary bureaucracy or proportional increases in overhead.
• Develop Finance and Operations leaders, clarify responsibilities, and build a culture of accountability, responsiveness, and continuous improvement.
• Work with Sales and other functional leaders to balance growth, profitability, customer experience, and cash flow.

Benefits

• Competitive quarterly incentive opportunity.
• Professional development programs, including improv-based learning with Second City Works.
• Opportunities to network with innovators, executives, and emerging talent through Chicago Innovation.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive