IT Account Executive- OSG

A bit about Lyra…

Lyra Technology Group is a family of industry leading technology service businesses. Our companies are operated independently by exceptional management teams. Companies that join our group retain the employees, name, and culture that have made them successful. As a platform of Evergreen Services Group, we never divest from businesses we partner with and approach every decision with the goal of driving sustainable and healthy growth over the long term.

IT Account Executive-Lyra Technology Group

Lyra Technology Group is seeking a IT Account Executive for one of their operating companies, Outsource Solutions Group.  As an IT Account Executive, you'll play a critical role in expanding our client base. We are looking for a tech-savvy professional who thrives in a fast-paced environment and is passionate about helping businesses optimize their technology infrastructure.

About Outsource Solutions Group…

Outsource IT Solutions Group (OSG) is a full service IT development, networking, and IT maintenance company serving clients in Chicagoland area since 1998. Outsource entered the market at the leading edge of networking and complex technology systems – and we’ve been there ever since. OSG currently maintains a 20+ employee technical staff.  As an organization Outsource is a Microsoft Gold Certified Partner, Microsoft Small Business Specialist and Cisco Select Certified partner. OSG’s team of trained and certified technicians, engineers and customer service representatives all work together to ensure that your business IT needs are met at every level, from design and implementation to training and maintenance. OSG provides the following services: Managed IT services, Hyper-V server virtualization, cloud-based business continuity, Network Design, LAN/WAN Troubleshooting, Remote Connectivity design and implementation, local and cloud-based e-mail hosting, cloud-based e-mail security, queuing, and archiving, Internet gateway design and security and competitive pricing on hardware/software.

Your work as an IT Account Executive will include several components: 

• Client Acquisition & Relationship Management: Identify, engage, and secure new business opportunities through outbound prospecting, networking, and referrals. Build and maintain strong relationships with clients to understand their IT needs and deliver tailored solutions.
• Solution Selling: Present and sell Outsource IT’s full suite of services—including managed IT support, cybersecurity, cloud solutions, and infrastructure upgrades—to small and mid-sized businesses across various industries.
• Consultative Approach: Conduct discovery meetings and technology assessments to understand client pain points. Collaborate with technical teams to develop proposals that align with client goals and budgets.
• Pipeline & Forecasting: Manage sales pipeline using CRM tools (e.g., Salesforce or similar), track progress against KPIs, and provide accurate forecasts to leadership.
• Vendor Coordination: Work with internal procurement and vendor partners to source hardware, software, and licensing solutions that meet client specifications.
• Market Intelligence: Stay current on industry trends, emerging technologies, and competitor offerings to position Outsource IT as a trusted advisor.

Our ideal IT Account Executive has the following qualifications:

• 2+ years of B2B sales experience, preferably in IT services or technology solutions
• Strong understanding of IT infrastructure, cloud services, and cybersecurity concepts
• Excellent communication, presentation, and negotiation skills
• Proficiency with CRM systems and Microsoft Office Suite
• Self-motivated, goal-oriented, and able to work independently
• Bachelor’s degree in Business, Marketing, or a related field preferred

The targeted salary for this role is $80,000-$100,000 per year and will operate out of the Naperville office on a hybrid basis. If you're motivated by meaningful client relationships, strategic selling, and a dynamic work environment, we want to hear from you!