Professional Sales Representative

60k salary - 5% commission on sales Guesswork IT Solutions, Inc. is a Managed Service Provider (MSP) and a Telecom Service Provider dedicated to delivering reliable, scalable, and secure IT solutions for small and mid-sized businesses. We simplify technology, build long-term client relationships, and provide support that feels like an extension of our clients’ teams. We are growing and seeking a driven Sales Representative who is passionate about helping businesses improve their technology and security posture. Position Overview: The Sales Representative is responsible for identifying new business opportunities, building a strong pipeline, and closing deals for our managed IT services, cybersecurity offerings, cloud solutions, project-based services and phone service offerings. This role is ideal for someone who understands the MSP space, thrives in a consultative sales environment, and enjoys turning client challenges into tailored IT solutions. Key Responsibilities: Prospect, qualify, and develop new business leads through outbound calls, email campaigns, networking, and referrals. Conduct discovery meetings to understand client technology needs, pain points, and operational goals. Present and explain Guesswork IT Solutions’ service offerings in a clear, compelling, and technically confident manner. Build and manage a healthy sales pipeline using CRM tools. Create proposals, quotes, and scopes of work for managed services, cybersecurity packages, IT projects, and phone services/systems. Collaborate with technical teams to ensure accurate solution design and successful handoff after closing deals. Meet or exceed monthly and quarterly sales targets. Represent the brand at local events, trade shows, and community organizations. Foster strong, trust-based relationships with prospects and clients. Qualifications (Required): 1–3+ years of sales experience, ideally in MSP, SaaS, or IT services. Strong communication and presentation skills. Ability to understand and explain technical concepts in simple terms. Self-motivated, goal-oriented, and comfortable working independently. Experience using CRM platforms. Qualifications (Preferred): Prior experience selling MSP services, cybersecurity solutions, cloud offerings, or phone systems/services. Familiarity with common SMB IT environments such as Microsoft 365, networking basics, and backup solutions. Existing local business relationships or networks. What We Offer: Competitive base salary plus commission. Flexible work environment with remote and hybrid options. Ongoing training in IT service offerings and MSP best practices. Opportunities for career growth as Guesswork IT Solutions expands. A supportive, team-oriented culture where your ideas matter. Job Type: Full-time Benefits: 401(k) 401(k) matching Dental insurance Health insurance Life insurance Paid time off Vision insurance Work Location: In person - Travel Required