Account Director (Individual Contributor) – Microsoft-Focused IT Services / U.S. Growth Role (Chicago)

Job Description

Join a well-established $100M IT services and managed services provider entering a pivotal U.S. expansion phase. With a strong foundation in technical execution and deep Microsoft expertise, the company is now investing in formal sales leadership, structure, and go-to-market focus across the U.S.

This is a high-impact opportunity for a consultative, outcome-driven seller who thrives in complex environments and wants to play a visible role in scaling U.S. revenue.

In this role, you will be:

• Owning and expanding net-new logo acquisition across mid-market to small enterprise accounts ($50M–$2B revenue)
• Leading consultative, multi-threaded sales cycles across cloud, managed services, ERP/Dynamics 365, data & AI, application modernization, and security
• Diagnosing complex business and technical challenges and mapping solutions across the Microsoft ecosystem
• Partnering closely with Microsoft on co-sell motions, target accounts, and lead generation
• Pulling in technical SMEs and delivery leaders to build proposals and close sophisticated, outcome-based deals

What makes this opportunity unique?

• High-visibility role during a U.S. growth inflection point with limited current sales coverage
• Deep Microsoft-first organization (≈80% Microsoft-based revenue) with top-tier global partner distinctions
• Ability to leverage nearshore delivery resources to support enterprise-grade U.S. clients with strong cost efficiency
• Proven ability to displace large global systems integrators in ERP, cloud, and modernization initiatives
• Strong executive alignment and commitment to formalizing sales leadership and GTM strategy

Territory & Deal Profile:

• Entry deals starting as small as ~$1K MRR
• Typical recurring engagements: $20K–$60K MRR
• Larger project-based work up to ~$1M ARR
• Sales cycles ranging from fast-moving to enterprise-length, depending on scope and urgency

Compensation & Benefits:

• Base Salary: $130K–$160K (DOE)
• OTE: $260K–$320K (50/50 split, uncapped commission)
• Medical, Dental & Vision
• HSA / FSA options
• 401(k) match
• Strong employer contribution toward benefit costs

Hardest part of the job?

 

Successfully navigating complex, technical buying environments while selling across a broad Microsoft ecosystem. Top performers excel at diagnosing interconnected systems (starting with ERP), selling outcomes – not products – and leading stakeholders through ambiguity.