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.

· 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 goals—then 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.

· 3–7+ 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/executives—focusing 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