Director of Pre-Sales

CompassMSP helps organizations simplify, power, and protect their businesses through managed IT, cybersecurity, cloud, compliance, and strategic technology services. 
We serve enterprise and mid-market organizations through a security-first approach that combines national capabilities, regional expertise, proactive support, and practical business guidance. 
Our teams work closely with clients to reduce risk, improve productivity, modernize their technology environments, and align technology investments with their broader business objectives. 
Role Requirements

• 5+ years of experience in business-to-business (B2B) corporate sales.
• 3+ years of experience in pre-sales, solution consulting, sales consulting, sales enablement, or complex deal support.
• 3+ years of experience working within an MSP, MSSP, IT-services, cybersecurity-services, telecom, or any IT-related industry
• Demonstrated success supporting complex, multi-stakeholder sales cycles.
• Strong understanding of consultative and value-based selling methodologies.
• Experience leading discovery sessions, presentations, proposal reviews, demonstrations, and executive-level conversations.
• Experience coordinating proposals, RFP responses, pricing, and internal approvals.
• Strong commercial judgment and understanding of recurring-revenue sales.
• Ability to translate technology and service concepts into clear business value adds.
• Strong professional presence and strong verbal, written, and presentation skills.
• Demonstrated ability to coach sellers and improve sales performance.
• Experience working with Sales, Marketing, Finance, Operations, Legal, and Service Delivery.
• Strong organizational skills and the ability to manage multiple opportunities and competing deadlines.
• Comfort working in a growing, geographically distributed, and evolving organization.
• Ability to travel approximately 30%.

*Preferred Qualifications

• Experience building or transforming a pre-sales function within an MSP.
• Experience supporting both new-client acquisition and existing-client expansion.
• Experience selling fully managed and co-managed IT services.
• Experience supporting cybersecurity, cloud, compliance, advisory, or professional-services sales.
• Experience selling into regulated industries such as healthcare, financial services, legal, manufacturing, construction, or government contracting.
• Familiarity with CRM software, proposal-management, sales-enablement, and CPQ platforms.
• Experience developing sales playbooks, proposal libraries, qualification frameworks, and sales-training programs.
• Experience supporting channel partners, referral partners, or strategic alliances.
• Bachelor’s degree in business, marketing, communications, information technology, ora related field, or equivalent professional experience.

Role Responsibilities

• Develop and maintain a structured discovery methodology for new sales opportunities.
• Lead or support discovery conversations with business leaders, executives, IT stakeholders, operations teams, and procurement.
• Coach the sales organization on asking effective discovery questions and uncovering client needs beyond the initial request.
• Translate discovery findings into a clear opportunity strategy and client value proposition.
• Ensure that discovery information is documented accurately and consistently in the CRM.
• Help sellers position managed IT, cybersecurity, cloud, compliance, strategic advisory, and professional services in clear business terms.
• Coordinate with internal technical, operational, security, and service-delivery subject-matter experts when specialized input is required.
• Translate internal recommendations into client-friendly language focused on value, outcomes, risk reduction, productivity, resilience, and scalability.
• Ensure that proposed services are aligned with CompassMSP’s current capabilities and approved offerings.
• Vet and prevent sales commitments that are unclear, unsupported, or inconsistent with CompassMSP’s delivery model.
• Sales Presentations and Demonstrations (subject matter expert for all high-value sales opportunities
• Proposal and RFP Management (develop, coordinate, and lead)
• Pricing and Commercial Coordination
• Deal Strategy and Sales Execution (identifying patterns, covering objections, competitive positioning, and navigation complex buying groups.)
• Sales Enablement oversight, creation, implementation, and execution
• Sales-to-Delivery Handoff
• Process and Performance Management

Benefits

• Competitive annual base salary
• Quarterly Bonuses
• Flexible, unlimited PTO
• Medical/Dental/Vision/Life/Disability coverage available
• 401k with company match
• Career Development & Coaching
• Fun work environment!