Services Sales Executive

Location: Chicago, IL, United States

Salary: $100,000–$130,000 per annum, excluding commission and other variable compensation.

Company

hirify.global delivers technology solutions for enterprise and midmarket clients across the United States and Canada, including application modernization, managed hybrid cloud, cybersecurity, unified communications, and infrastructure services.

What you will do

• Originate, qualify, shape, and close complex Professional Services opportunities valued at $5M–$50M+.
• Lead consultative discovery, end-to-end sales strategy, proposal development, pricing, negotiation, and commercial execution.
• Translate customer needs into advisory, assessment, implementation, transformation, and managed services offerings.
• Coordinate Account Executives, Account Managers, solution leaders, architects, engineers, advisory teams, and delivery specialists.
• Build executive relationships, guide complex stakeholder decisions, and connect technology investments to measurable business outcomes.
• Stay engaged after the sale to protect delivery outcomes, resolve critical risks, and identify expansion and recurring-revenue opportunities.

Requirements

• 10–15+ years of experience in enterprise services sales, consulting, or services-led environments.
• 5+ years of selling outcome-based Professional Services through Statements of Work.
• Proven ownership of large, complex deals from inception through close, including drafting customer-facing SOWs.
• Experience working with technical presales, solution architecture, engineering, and delivery teams.
• Background in an MSP, GSI, or large-scale consulting organization.
• Expertise in consultative selling, commercial structuring, pricing, negotiation, CRM discipline, and quota achievement; Salesforce experience is preferred.

Nice to have

• Experience selling cloud and infrastructure, application modernization, software development, data and AI, cybersecurity, or unified communications services.
• Experience with multi-year transformation programs, project-based and managed services delivery models, or matrixed organizations.

Culture & Benefits

• Competitive base salary with performance-based incentives tied to bookings and gross profit contribution.
• Opportunity to lead high-visibility strategic pursuits and influence major client transformation programs.
• Access to partner ecosystems, co-sell programs, and joint go-to-market resources.
• Professional development budget for certifications, conferences, and advanced training.
• Collaborative services community focused on sharing knowledge, assets, and successes.