Outside Sales Representative

Outside Sales Representative

This is a hunter-focused role. You'll build pipeline from scratch, close high-value managed services contracts (typically multi-year agreements representing substantial annual commitments), and contribute directly to our goal of adding ~$40,000 in new Monthly Recurring Revenue (MRR) annually through ~200 new end-users (A typical account will have approximately 30 end users). Expect consultative selling: walking into businesses, uncovering real pain points (cyber risk, compliance, costly downtime), and positioning Christo IT as the trusted partner that prevents problems before they start. This is a hybrid role, with regular in-office presence Monday - Thursday, as well as local travel to prospect sites.

Key Responsibilities

Prospect and generate leads in our target markets (small/mid-sized businesses in the Philadelphia region and beyond) through cold outreach, networking, referrals, events, and targeted campaigns.

Conduct discovery meetings to understand business challenges, IT pain points, and goalsthen translate how our services deliver measurable value (e.g., reduced risk, predictable costs, compliance support).

Present tailored solutions, demos, and proposals to owners, executives, and decision-makers.

Negotiate and close high-dollar, recurring contracts with confidence and integrity.

Manage full sales cycle: follow-ups, handling objections, coordinating with our technical team for assessments/demos, and setting clear expectations post-sale.

Maintain accurate CRM records (ConnectWise), forecast pipeline, and report on activity/progress toward goals.

Attend trade shows, local events, and industry networking to build awareness.

Stay informed on competitors, market trends, and client industries to refine messaging.

Skills, Knowledge and Expertise

37+ years of proven B2B sales experience successfully closing high-value contracts (e.g., $10k$100k+ annual recurring value per deal) in technology, SaaS, professional services, telecom, or similar complex/solution sales.

Demonstrated ability to sell consultatively to small business owners/executivesfocusing on business outcomes (ROI, risk mitigation, efficiency) rather than technical specs.

Comfortable with technology concepts and eager to learn our services deeply enough to explain value convincingly (no deep IT certs required, but quick learner a must).

Strong hunter mentality: self-starter who thrives on prospecting and building pipeline independently.

Excellent verbal/written communication, presentation, and relationship-building skills.

Proficient in Microsoft Office (especially Outlook, Excel, PowerPoint); CRM experience (ConnectWise a plus).

Valid driver's license and reliable vehicle for local travel.

About ChristoIT

At Christo IT, we deliver proactive managed IT, cybersecurity, cloud, and VoIP solutions that protect small to mid-sized businesses (especially in medical, legal, financial, and professional services) from disruptions, breaches, and downtime. Our multi-layered security approach follows the NIST Framework, providing peace of mind so owners can focus on growthnot IT headaches. We're a tight-knit, values-driven team that's grown steadily through exceptional service and client relationships. Now, we're ready to accelerate: We're seeking a proven sales professional to own net-new client acquisition and help us add significant monthly recurring revenue.