IT Sales Account Executive (US Managed IT Services, WFH)

What are we looking for?

We are seeking an IT Sales Account Executive to manage and convert inbound leads while maintaining the discipline to generate their own pipeline when lead flow slows. This role is not purely a hunting position — the primary expectation is working inbound opportunities effectively and moving them through the sales process. However, the ideal candidate understands that a healthy pipeline requires consistent proactive effort, and will take initiative to develop new prospects before gaps emerge. They must be able to hold credible conversations about IT challenges at a business level and position managed services as the right solution.

Skills Required

• 3+ years of B2B sales experience with at least 2 years selling managed IT services or technology solutions
• Demonstrated ability to run a full sales cycle independently: hunt, qualify, propose, and close
• Familiarity with core MSP service categories: endpoint management, cybersecurity, cloud services, network infrastructure, and help desk
• Experience selling to SMB and/or mid-market clients across multiple verticals
• Strong discovery and consultative selling skills, able to uncover business problems and connect them to technical solutions
• Comfortable presenting to both technical and non-technical stakeholders
• Proficiency with CRM tools for pipeline tracking and activity management (HubSpot, Salesforce, or similar)

Nice to have

• Experience with PSA or RMM platforms (ConnectWise, Autotask, Kaseya, etc.) as a point of reference in client conversations
• Familiarity with Microsoft 365 and Azure as sellable solutions within an MSP context
• Prior experience at an MSP, VAR (Value-Added Reseller), or IT services firm
• Understanding of cybersecurity frameworks and compliance requirements (HIPAA, CMMC, SOC 2) as they apply to client risk conversations
• Existing book of relationships within local business or tech communities
• What will you do?

Pipeline Development & Prospecting

• Work inbound leads promptly and thoroughly, qualifying, following up, and moving opportunities forward with urgency
• Own outbound prospecting efforts when inbound volume slows, including cold outreach, networking, referrals, and targeted campaigns
• Maintain consistent outbound activity even during periods of strong inbound flow, understanding that today's pipeline is built on last month's effort
• Proactively monitor pipeline health and take action before gaps appear, not after
• Build and maintain a healthy pipeline across SMB and mid-market segments
• Identify and engage key decision-makers including IT managers, Operations leads, and C-suite contacts

Sales Execution

• Lead the full sales cycle from first contact through needs discovery, proposal, and signed agreement
• Conduct discovery calls and on-site assessments to uncover IT pain points, gaps, and growth needs
• Develop and present tailored proposals that map client challenges to MSP service offerings
• Negotiate contracts and close new business while maintaining margin discipline

Technical Credibility

• Speak confidently at a business level about common IT challenges: cybersecurity risk, infrastructure reliability, cloud adoption, compliance, and help desk support
• Collaborate with technical engineers and solutions architects to validate scope and design accurate proposals
• Stay current on MSP offerings, vendor solutions, and emerging IT trends relevant to client needs

Client Relationship & Handoff

Manage the transition from closed deal to service delivery in partnership with the technical team

Maintain relationships with new clients through onboarding to ensure satisfaction and identify expansion opportunities

Represent the company at local business events, industry groups, and networking functions

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Equal Employment Statement

Employment decisions at ConnectOS will be conducted without consideration of factors such as age', race, color, religion, gender, disability status, sexual orientation, gender identity or expression, genetic information, and marital status. ConnectOS ensures the full confidentiality of the data it processes.