Outside Sales Representative – MSP/MSSP Sales Location: Orlando, Hybrid – weekly office meetings, periodic tradeshows and industry events, weekly on-site client visits as required

Be one of the first applicants, read the complete overview of the role below, then send your application for consideration. Department: MSP Sales Reports to: VP of Growth Employment Type: Full-Time Compensation: Competitive Base + Benefits with Uncapped Variable Compensation ($150K OTE) Pine’s portfolio company, i-Tech Support Services Inc., is hiring for an Outside Sales Representative – MSP/MSSP Sales. Position Summary We are seeking an experienced outside sales representative to drive the growth of our Managed IT Services (MSP) and Managed Security Services (MSSP) offerings in the SMB market. This is a quota-carrying hunter-farmer role for someone who can both develop new relationships and deepen existing ones. You will be the face of the company — meeting clients at their locations, attending trade shows, and engaging with industry associations. You are the bridge between technology and client success. The ideal candidate has a solid understanding of IT fundamentals and excels at aligning technology solutions with real business outcomes. Equally important, you will work cross-functionally with operations, service delivery, and technical teams to ensure successful onboarding, ongoing satisfaction, and contract expansion. Key Responsibilities New Business Development Proactively prospect and engage SMBs through cold outreach, networking, and referrals

Lead discovery sessions to uncover business drivers, IT challenges, and risk areas

Develop proposals and close multi-year recurring services agreements (MSAs, SLAs)

Educate prospects on the value of proactive IT and cybersecurity services over reactive support

Identify opportunities to cross-sell ERP or other services

Industry Verticalization and Expertise Ability to quickly develop subject matter familiarity across SMB segments such as: Healthcare (HIPAA-driven IT and cybersecurity requirements)

Financial Services (compliance-focused solutions and layered security)

Manufacturing/Distribution (operational continuity and infrastructure scalability)

Education and Non-Profit (grant-funded technology, compliance support)

Understand the unique operational challenges within each vertical and tailor consultative selling approaches accordingly

Stay current with industry trends, regulatory changes, and risk profiles impacting SMBs in each target segment

Position i-Tech’s managed and security services as tailored, scalable solutions to meet vertical-specific needs

Sales Process & Operations Maintain and track pipeline and activity in CRM (e.g., HubSpot, Salesforce)

Provide sales forecasts, activity reports, and competitive intelligence to leadership

Follow all internal processes for quoting, contract execution, and onboarding handoffs

Coordinate closely with internal technical and operations teams during presales and transition phase

Required Competencies IT Technical Acumen Familiarity with core MSP service areas: Remote Monitoring & Management (RMM)

Help Desk & End-User Support

Backup & Disaster Recovery (BDR)

Endpoint & Network Security

Microsoft 365, Azure, and cloud-based infrastructure

Understanding of cybersecurity service models: Security Information & Event Management (SIEM)

Vulnerability Management

Compliance support (HIPAA, CMMC, etc.)

SOC/SOCaaS offerings

Able to effectively translate technical concepts into business value

Strong adherence to CRM discipline, with working knowledge of HubSpot for pipeline management, deal tracking, and activity logging

Business and Financial Understanding Strong grasp of SMB business models and budgeting dynamics

Able to frame IT services as risk mitigation, operational efficiency, and ROI

Skilled at identifying business risk, compliance exposure, and growth barriers

Familiar with how to navigate multi-stakeholder buying processes

Experience and Qualifications 3+ years of outside B2B sales experience, ideally in MSP/MSSP or IT services

Proven record of meeting or exceeding quota in a recurring revenue model

Strong mix of new business development and account management

Experience selling to business owners, CFOs, and non-technical decision-makers

Excellent verbal and written communication skills

Experience with HubSpot Sales or similar CRM, ZoomInfo, cold calling, and business development

Compensation and Benefits Competitive base salary with uncapped commission plan

Performance-based incentives and bonuses

Comprehensive medical, dental, and vision insurance with competitive plan options (including orthodontics)

22 paid days off: 15 PTO + 7 national holidays

Company-provided basic life insurance and long-term disability

401(k) program with employer match

Paid parental leave

Company-issued laptop

Ongoing technical sales training and certifications

About Us i-Tech Support Services Inc. is a strategic technology partner helping SMBs grow and protect their businesses through Managed IT Services, Cybersecurity, and Cloud ERP (Acumatica) solutions. Our approach is rooted in reliability, security, and long-term client partnerships.

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