Seeking a relationship-focused sales professional with sufficient technical fluency to independently communicate the value of proactive MSP services, answer client questions confidently, and lead discussions without relying on constant technical staff support. This role is about strategic advisory selling: connecting IT solutions to clients' business goals, translating concepts bidirectionally, and proactively managing longer sales cycles (often 6-12 months) to build enduring partnerships. You will position client as a trusted advisor - not a feature vendor - driving trust through genuine discovery, so clients remain for years and refer others. Key Responsibilities Secure and nurture long-term, high-fit client relationships - Prospect and engage qualified Chicago-area SM - Bs, enterprises, and AEC firms; conduct deep discovery to build genuine trust through advisor-style listening and follow-through, resulting in multi-year partnerships and referrals. Drive revenue through strategic, business-aligned sales - Independently qualify prospects, assess needs, and close deals by clearly connecting client's proactive solutions (e.g., cybersecurity, cloud, managed IT) to clients' strategic objectives like risk reduction, operational efficiency, and growth. Own and advance the full sales cycle with discipline - Manage pipeline in Hub. Spot CRM and create compelling proposals/ RFP responses in Bidsketch (or similar) to maintain momentum in extended 6-12 month cycles, including proactive coordination and seamless onboarding handoffs. Serve as the effective, independent bridge - Communicate technical value in plain language to executives, translate business requirements back to technical teams, and lead discussions confidently without constant escalation. Must-Have Skills & Qualifications Technical Fluency - Broad understanding of IT environments and client's solutions (networks, cloud, cybersecurity, backups, asset management) to speak intelligently about services, answer prospect questions confidently, and hold technical discussions without constant escalation. Business Outcome Orientation - CIO-level perspective; ability to connect IT services to clients' strategic goals (efficiency, risk reduction, growth) rather than feature selling. Communication & Translation - Excellent at simplifying technical ideas for non-technical executives and accurately conveying business requirements to technical teams - strong bidirectional communicator. Process-Driven & Proactive - Highly organized and self-directed; track record of driving long sales cycles (6-12 months) through structured discovery, timely follow-ups, and internal alignment. Relationship Building - Consultative approach focused on genuine discovery, active listening, and trust-building; history of cultivating long-term advisor-client partnerships. Sales Experience - 3 years in B 2 B IT/ MSP or technical solutions sales; consistent quota achievement via consultative/relationship selling. Tool Proficiency - Proficient in Hub. Spot CRM for pipeline/funnel management, workflows, forecasting, and contact/deal tracking; experienced with Bidsketch (or Panda. Doc/ Proposify/ Qwilr/ Nusii or similar) for proposals/ RFPs. Self-Motivated & Organized - Thrives independently in a fast-paced, client-centric environment. Preferred Qualifications Experience with Bidsketch in MSP/ IT sales. Proven success selling to Chicago SM - Bs, enterprises, or AEC sectors. Familiarity with partners like Microsoft, Cisco, Dell, Datto, and similar. Interest in eco-friendly IT and trends such as AI, proactive cybersecurity, and 2026 planning. Bachelor's degree in Business, IT, or related field. Benefits Competitive Compensation - Base salary commission rewarding revenue impact and long-term client wins. Thriving Market - Sell in the Chicago market backed by 25 years of expertise, strong vendor alliances, and a focus on strategic, enduring client relationships. Collaborative Culture - Join a supportive team that values proactive service, environmental responsibility, and genuine client partnerships. Work-Life Balance - Hybrid/flexible work environment contributing to Worry-Free IT that empowers businesses. Location: Hybrid / Chicago Area Chicago, IL, is a vibrant city known for its rich history, diverse culture, and thriving business community. With a strong economy and numerous opportunities for professional growth, Chicago offers an ideal environment for career advancement. Benefits