Location: Orlando, Hybrid – weekly office meetings, periodic tradeshows and industry events, weekly on-site client visits as required
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.
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.
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
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
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
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
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
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
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
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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