Account Executive – Managed IT Services; MSP

Greater Chicago Area (Chicago, IL)

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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

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.

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.

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/Prefferedskills
  :
  Sales Chain CRM experience.

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

Dedicated technical pre-sales engineering and marketing lead generation support