Chief Operating Officer Greater Chicago, IL Area

The Opportunity

Heartland is a growing technology solutions provider serving commercial and enterprise customers with technology products, managed services and professional services. We are seeking an experienced COO to join our executive leadership team and help build the operating foundation for our next stage of growth.

As the CEO's operating partner, you will translate strategy into disciplined execution, profitable growth and measurable results. You will report to the CEO and lead Operations and Finance, establishing the processes, systems and accountability needed to scale our solutions and services businesses.

This is a hands-on executive role for someone who can set direction, analyze financial performance, develop leaders, and work alongside teams to solve problems. Prior leadership experience with a value-added reseller (VAR), managed services provider (MSP), or comparable IT solutions company delivering technology products and services is required. Given the hands-on, collaborative nature of this role, the COO must be local.

What You Will Lead

Operating execution and accountability. Partner with the CEO and executive team to turn strategy into operating plans, financial goals and clear ownership. Establish a regular operating cadence with KPIs, performance reviews, and follow-through.

Finance and business performance. Lead Finance and Accounting, including reporting, budgeting, forecasting, internal controls and coordination with banking, tax and audit partners. Deliver timely visibility into gross profit, EBITDA, cash flow and profitability by customer, service and business line. Help evaluate investments and strategic opportunities.

Product operations. 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.

Services delivery and profitability. 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.

Working capital and vendor economics. 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.

Systems and scalable processes. 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.

Leadership and team development. Develop Finance and Operations leaders, clarify responsibilities and build a culture of accountability, responsiveness and continuous improvement. Work closely with Sales and other functional leaders to balance growth, profitability, customer experience, and cash flow.

What You Bring

Relevant leadership experience. 10+ years of progressive leadership, including significant responsibility for operations and financial performance within a VAR, technology reseller, distributor or comparable product-centric IT solutions company.

Strong financial and P&L acumen. Demonstrated experience with budgeting, forecasting, gross-margin management, working capital and cash flow, with a track record of improving profitability and operating performance.

Understanding of reseller economics. Practical knowledge of hardware and software resale, procurement, fulfillment, manufacturer programs, distribution relationships, rebates and special pricing.

Ability to scale operations. Success improving systems, data quality, and cross-functional processes. Experience leading managed or professional services operations is highly valued.

Hands-on, collaborative leadership. Strong analytical judgment, clear communication and the ability to develop leaders, hold teams accountable and execute in an entrepreneurial environment.

A bachelor's degree in business, finance, accounting, or a related field is preferred. An MBA, CPA, or equivalent financial experience is beneficial but not required.

What Success Looks Like in Year One

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. You will establish an accountable leadership cadence and an operating model that supports continued growth.

Our Culture

Heartland's success is built on a foundation of core values: passionate, dedicated, agile, collaborative team players, and strategic creativity. We are also guided by strong values and a commitment to delivering exceptional customer service. Our commitment is strong to our customers and technology partners to earn their trust and be viewed as their best partner.

At Heartland, we invest in our people and our culture. Our professional development programs have included improv‑based learning with Second City Works, building communication, collaboration, and leadership skills in an interactive, hands‑on way. We partner with Chicago Innovation to network with the city's top innovators, executives, and emerging talent, bringing fresh ideas back to our business. Our work has earned us recognition as Honeywell's Partner of the Year for two consecutive years, reflecting our technical expertise, collaborative approach, and commitment to exceptional service.

Location: McHenry, Illinois | Combination of hybrid and onsite. This role is best suited for candidates who live within commuting distance of McHenry. Relocation assistance is not available.

Base salary: $180,000–$225,000, depending on experience and qualifications, plus eligibility for a competitive quarterly incentive opportunity.

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