Account Executive – Managed IT Services (MSP)

Location: Greater Chicago Area (Hybrid / Client-Facing | Elmhurst / Oak Brook corridor)

Compensation: $75,000 – $95,000 Base Salary + Uncapped Commission (Target First-Year OTE: $140,000 – $180,000+)

Employment Type: Full-Time, Permanent

Benefits: Comprehensive Medical, Dental, Vision, 401(k) with Company Match, Vehicle/Mileage Allowance, Generous PTO, and Paid Holidays

About the Opportunity

A premier, established regional business technology provider in the Greater Chicago area is expanding its core solutions portfolio and seeking an ambitious, consultative Account Executive – Managed IT Services.

Known for decades of excellence in enterprise office technology and workflow solutions, our client has built a comprehensive Managed Service Provider (MSP) practice delivering end-to-end IT support, cloud infrastructure, network architecture, and advanced cybersecurity solutions to small and mid-market commercial businesses.

In this role, you will be the primary driver of net-new Monthly Recurring Revenue (MRR). You will target C-level executives, business owners, and IT decision-makers across the Chicagoland footprint—both by hunting new greenfield commercial accounts and strategically cross-selling Managed IT into an extensive existing base of commercial clients.

Key Responsibilities

• Drive Net-New MRR: Prospect, qualify, and close new commercial Managed IT service agreements (contracted monthly recurring revenue) across key Chicago suburban and metro business corridors.

• Consultative Discovery & IT Assessments: Conduct high-level business discovery meetings with business owners, CFOs, and IT directors to uncover vulnerabilities in network security, data backup/disaster recovery, cloud readiness, and helpdesk support.

• Solution Architecture Partnership: Collaborate closely with internal Sales Engineers and vCISOs to design tailored MSP proposals, Statements of Work (SOWs), and multi-year service level agreements.

• Cross-Selling & Client Expansion: Partner with internal account managers to identify Managed IT and cybersecurity cross-sell opportunities within the company’s existing office technology account base.

• Pipeline & Sales Discipline: Maintain an active multi-touch prospecting cadence (phone outreach, executive networking, on-site discovery, and referral partner development) while tracking pipeline stages accurately in CRM.

Qualifications

• 2+ Years of B2B Managed IT / MSP Sales Experience: Proven track record selling recurring Managed IT Services, network infrastructure, cybersecurity stacks, Microsoft 365/cloud migrations, or SaaS IT solutions.

• Fluency in the MSP Business Model: Clear understanding of Monthly Recurring Revenue (MRR), per-user/per-device pricing models, Service Level Agreements (SLAs), and IT risk mitigation.

• True Hunter Mentality: Demonstrated discipline and success building a pipeline through proactive outbound prospecting, cold outreach, and consultative face-to-face discovery.

• C-Suite Presence: Executive communication and presentation skills; comfortable discussing risk, compliance, operational downtime, and IT budgets with non-technical business owners and CFOs.

• Territory Logistics: Reside within a commutable distance of the Greater Chicago area with a valid driver’s license and dependable vehicle for local client meetings.
   
• Bonus/Preffered skills: SalesChain CRM experience.

Total Rewards & Perks

• Competitive base salary paired with an aggressive, uncapped commission structure with accelerators on new MRR

• Comprehensive Health, Dental, and Vision insurance plans

• 401(k) retirement plan with employer matching

• Monthly auto allowance and mileage/expense reimbursement

• Modern technology package (laptop, smartphone allowance, CRM tools)

• Dedicated technical pre-sales engineering and marketing lead generation support