[Hiring] Sales Development Representative / Appointment Setter @ScalableOS

Role Description

We are seeking a seasoned Sales Development Representative (SDR) with a strong background in MSP/MSSP sales to generate new business opportunities among small to mid-sized businesses (SMBs) with 10–300 employees. This role is laser-focused on setting qualified first-time appointments with business owners, executives (CEO, CFO, COO), and IT leaders (IT Directors, IT Managers) who are responsible for technology and cybersecurity decisions. The ideal candidate understands the challenges SMBs face in managing IT, cybersecurity, compliance, and cloud services and can effectively communicate the value of a trusted managed services partner.

• Proactively identify and prospect SMB organizations (10–300 employees) in target industries such as healthcare, banking/finance, manufacturing, government, and professional services.
• Secure first-time meetings with business owners and executive decision-makers by highlighting the value of managed IT and cybersecurity services.
• Educate prospects on how our services solve common SMB pain points: limited IT staff, rising cybersecurity risks, compliance requirements, and budget constraints.
• Execute outbound campaigns through calls, emails, LinkedIn, and events to generate qualified leads.
• Nurture inbound leads to move them into the sales funnel.
• Maintain accurate records of leads, activity, and appointments in CRM (HubSpot).
• Consistently meet weekly and monthly activity/appointment-setting targets.
• Collaborate with marketing on SMB-focused campaigns and leverage content to enhance outreach.
• Provide insights on prospect challenges and trends within the SMB market to help refine sales strategies.

Qualifications

• Experience: 3–5+ years in appointment setting, inside sales, or sales development with a proven track record of engaging SMB clients (10–300 employees).
• Industry Knowledge: Strong understanding of SMB needs in managed IT services, cloud solutions, and cybersecurity compliance (NIST, HIPAA, SOC, CIS).
• Communication Skills: Ability to clearly explain IT and cybersecurity value to both business leaders and technical managers.
• Track Record: Success in setting meetings with SMB owners, executives, and IT managers.
• Tools: Familiarity with CRM systems (HubSpot), LinkedIn Sales Navigator, and prospecting platforms.
• Work Style: Persistent, professional, and comfortable overcoming objections while building rapport with SMB decision-makers.
• Education: Bachelor’s degree in Business, Marketing, IT, or related field or equivalent experience is a big plus.

Requirements

• Should be willing to accept a long-term work-from-home arrangement.
• Should be amenable to a permanent night shift schedule.