Account Executive – Managed Services (MSP) (Chicago)
Bowman Williams, Chicago, Illinois, United States, 60290
We are a boutique, white-glove Managed Service Provider supporting Chicago-area businesses for more than 25 years. The team is small, tight-knit, and built around consistency, proactive service, and long-term relationships. This is not a high-volume transactional shop. It’s a relationship-first MSP where reputation matters and leadership is hands-on and invested in doing things the right way.
We are hiring an experienced MSP sales professional who can confidently run discovery, speak the language of managed services, and translate technical conversations into business value. You will work directly with ownership and marketing to build pipeline, nurture opportunities, and close recurring revenue business.
What You Will Do • Own the full front-end MSP sales cycle including prospecting, discovery, qualification, and relationship development • Run consultative conversations with business owners and leadership teams • Clearly explain managed services, cybersecurity, backup, cloud, and risk mitigation in business terms • Build and manage pipeline in HubSpot with disciplined follow-up and deal tracking • Drive new MRR through managed services agreements, security add-ons, and cloud initiatives • Bring technical leadership into conversations only when deeper validation is required • Maintain consistency through longer sales cycles
What You Bring • 3+ years of B2B MSP sales experience • Strong understanding of MSP services including monitoring, patching, EDR, backup, RTO/RPO, and cloud fundamentals • Ability to communicate confidently with C-level decision makers • CRM-driven sales discipline (HubSpot preferred) • Relationship-first mindset with strong follow-through
Why This Role • 100% company-paid health and vision • Unlimited PTO • Small-team culture where your impact is visible • Leadership that prioritizes retention and long-term growth
We are hiring an experienced MSP sales professional who can confidently run discovery, speak the language of managed services, and translate technical conversations into business value. You will work directly with ownership and marketing to build pipeline, nurture opportunities, and close recurring revenue business.
What You Will Do • Own the full front-end MSP sales cycle including prospecting, discovery, qualification, and relationship development • Run consultative conversations with business owners and leadership teams • Clearly explain managed services, cybersecurity, backup, cloud, and risk mitigation in business terms • Build and manage pipeline in HubSpot with disciplined follow-up and deal tracking • Drive new MRR through managed services agreements, security add-ons, and cloud initiatives • Bring technical leadership into conversations only when deeper validation is required • Maintain consistency through longer sales cycles
What You Bring • 3+ years of B2B MSP sales experience • Strong understanding of MSP services including monitoring, patching, EDR, backup, RTO/RPO, and cloud fundamentals • Ability to communicate confidently with C-level decision makers • CRM-driven sales discipline (HubSpot preferred) • Relationship-first mindset with strong follow-through
Why This Role • 100% company-paid health and vision • Unlimited PTO • Small-team culture where your impact is visible • Leadership that prioritizes retention and long-term growth