Technical Sales Representative; MSP Sales

Chicago, IL (60607 Hybrid after ramp)

Join a boutique, white-glove MSP with 25+ years in the Chicago market, known for high-touch service and long-term client relationships. This is a high-impact, revenue-driving role with urgency—ideal for a consultative MSP seller who can build pipeline and close new business quickly.

You’ll work directly with ownership and marketing to drive new MRR, run discovery, and translate IT solutions into business value.

• Own full sales cycle: prospecting, discovery, qualification, and closing
• Run consultative conversations around managed services, security, and cloud
• Partner with marketing on targeted outreach and pipeline generation
• Manage pipeline and activity in Hub Spot (notes, follow-ups, deal stages)
• Drive new MRR (“seats”), projects, and long-term client relationships
• Bring in technical leadership only when needed for deeper validation

• 3+ years MSP sales experience (required)
• Ability to confidently sell managed services without engineering support
• Strong discovery, qualification, and follow-up discipline
• CRM-driven (Hub Spot preferred) and process-oriented

• Consultative, relationship-first sales approach
• Ability to translate technical concepts into business outcomes (risk, uptime, efficiency)
• Highly organized and comfortable managing longer sales cycles
• Thrives in a small, high-accountability environment

• % of MRR (monthly or first quarter) + project incentives