Outside Sales Representative

Role Overview

• Prospect and generate leads within target markets (small and mid-sized businesses in the Philadelphia region and surrounding areas) through cold outreach, networking, referrals, events, and targeted campaigns.
• Conduct discovery meetings to understand client business challenges, IT pain points, and growth goals.
• Translate those needs into clear, business-focused solutions that demonstrate value through reduced risk, predictable costs, and improved operational efficiency.
• Present tailored solutions, demonstrations, and proposals to business owners, executives, and other decision-makers.
• Negotiate and close recurring managed services contracts with professionalism and integrity.
• Manage the full sales cycle, including follow-ups, objection handling, coordinating with technical teams for assessments or demonstrations, and setting expectations post-sale.
• Maintain accurate CRM records, manage pipeline forecasts, and report on progress toward revenue goals.
• Attend industry events, trade shows, and local networking opportunities to build brand awareness and generate new opportunities.
• Stay informed on competitors, industry trends, and client market dynamics to refine messaging and positioning.

Requirements

• 3–7+ years of B2B sales experience successfully closing high-value contracts (typically $10K–$100K+ annual recurring value per deal) within technology, SaaS, telecom, professional services, or other solution-based sales environments.
• Demonstrated success selling consultatively to small business owners and executives, focusing on business outcomes such as ROI, risk mitigation, and operational efficiency rather than purely technical specifications.
• Comfort discussing technology concepts and willingness to learn managed services offerings deeply enough to communicate value effectively.
• Strong hunter mentality with the ability to independently prospect and build a pipeline from scratch.
• Excellent verbal and written communication skills, presentation abilities, and relationship-building capabilities.
• Proficiency in Microsoft Office (particularly Outlook, Excel, and PowerPoint).
• CRM experience preferred (ConnectWise experience is a plus).
• Valid driver's license and reliable vehicle for local travel.
• This role requires someone with integrity, positivity, and persistence—a sales professional who can confidently walk into a small business experiencing serious IT or security challenges and clearly demonstrate how proactive technology solutions can protect the organization and support long-term growth.
• The ideal candidate enjoys the challenge of building new relationships, closing meaningful deals, and contributing to the growth of a company where individual success directly impacts the organization’s trajectory.
• Please note that candidates must reside in the greater Philadelphia, PA area. This role will require onsite presence.