Outside Sales Representative STACK Cybersecurity | Livonia, Michigan Position Summary STACK Cybersecurity is seeking an experienced Outside Sales Representative to develop new business relationships and sell managed IT, cybersecurity, and compliance services to small and midsize businesses. This is a relationship-driven business development role. The Outside Sales Representative is responsible for building a pipeline, developing referral relationships, following up on qualified opportunities, meeting with prospective clients, understanding their business and technology needs, and moving opportunities through the sales process. The role works closely with STACK's inside sales, technical, and leadership teams. STACK's existing sales plan pairs inside sales appointment-setting activity with an Outside Sales Representative who takes qualified first-time appointments and advances those opportunities through the sales process. Responsibilities Develop new business opportunities for STACK's managed IT and AI practices, cybersecurity, and compliance. Build and maintain relationships with prospective clients, referral partners, business associations, and other sources of new opportunities. Attend networking events, association meetings, trade shows, and other business development activities. Conduct discovery meetings with business owners, executives, operations leaders, and IT decision-makers. Identify business, technology, cybersecurity, and compliance needs and determine whether STACK is an appropriate fit. Manage qualified opportunities from initial conversation through proposal, follow-up, negotiation, and close. Work with STACK's technical and leadership teams when an opportunity requires deeper technical or compliance expertise. Follow up consistently with prospects and maintain long-term relationships with opportunities that aren't ready to purchase immediately. Maintain accurate prospect, activity, opportunity, and follow-up information in the CRM. Coordinate with inside sales on leads and appointments and provide feedback that improves qualification and prospecting. Work with marketing on campaigns, events, content, and other activities designed to generate qualified opportunities. Develop relationships within STACK's target industries and local business community. Represent STACK professionally at client meetings and outside events. Maintain an active pipeline and provide accurate sales forecasts. Meet established goals for appointments, qualified opportunities, proposals, new recurring revenue, and closed business. Solutions Represented The Outside Sales Representative will develop enough working knowledge of STACK's services to identify opportunities and bring the appropriate technical expert into the sales process.

The current capabilities portfolio includes:

Managed IT Server and network management Help desk and endpoint management Microsoft 365 administration Backup, disaster recovery, and business continuity Cybersecurity Managed detection and response and endpoint detection and response Identity and access management Multi-factor authentication Ransomware prevention and incident response Security awareness training and phishing simulations Risk assessments and penetration testing Virtual Chief Information Security Officer services Compliance Cybersecurity Maturity Model Certification preparation and gap assessments National Institute of Standards and Technology Special Publication 800-171 implementation and documentation Supplier Performance Risk System score support Defense Federal Acquisition Regulation Supplement compliance SOC 2 Type II readiness and audit preparation Center for Internet Security Controls and Payment Card Industry Data Security Standard consulting Artificial intelligence governance and responsible AI policy development Qualifications Required Demonstrated business-to-business sales or business development experience. Experience developing new relationships rather than relying exclusively on inbound leads. Strong prospecting, networking, discovery, and follow-up skills. Ability to speak comfortably with owners, executives, IT leaders, and operational decision-makers. Experience managing a sales pipeline and maintaining accurate CRM records. Strong written and verbal communication skills. Ability to learn technical concepts and explain them in business terms. Comfortable attending outside meetings, networking functions, and industry events. Strong follow-through and personal accountability. Valid driver's license and ability to travel to customer and business development meetings in the region. Preferred Experience selling managed IT services, cybersecurity, technology, software-as-a-service, telecommunications, or another business-to-business professional service. Existing relationships in the Metro Detroit business community. Experience selling recurring-revenue services. Experience working with manufacturers, professional services firms, financial services companies, defense suppliers, or regulated businesses. Familiarity with cybersecurity or regulatory compliance. Deep cybersecurity expertise isn't required. The representative does, however, need to understand the business problems STACK solves and know when to involve a technical or compliance specialist. About STACK Cybersecurity STACK Cybersecurity provides managed IT, cybersecurity, and compliance services to small and midsize businesses. This includes support for manufacturers and defense supply chain businesses, managed IT services, cybersecurity services, and compliance programs including Cybersecurity Maturity Model Certification, National Institute of Standards and Technology Special Publication 800-171, Defense Federal Acquisition Regulation Supplement, Supplier Performance Risk System, and SOC 2 Type II.