Director of Pre-Sales
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Job Description
Director of Pre-Sales helping CompassMSP sell managed IT, cybersecurity, cloud, and compliance services. Leading discovery, proposals, pricing, deal strategy, enablement, and sales-to-delivery handoffs.
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
- Identify business objectives, challenges, operational pain points, growth plans, cybersecurity and compliance concerns, service expectations, budget considerations, decision criteria, key stakeholders, and desired outcomes
- Coach the sales organization on effective discovery questioning and uncovering client needs
- Translate discovery findings into opportunity strategies and client value propositions
- Document discovery information accurately and consistently in the CRM
- Develop sales narratives connecting CompassMSP’s managed IT, cybersecurity, cloud, compliance, strategic advisory, and professional services to client priorities
- Coordinate with technical, operational, security, and service-delivery subject-matter experts
- Lead or support executive presentations, discovery workshops, proposal reviews, demonstrations, and finalist meetings
- Prepare sellers and subject-matter experts for client interactions
- Oversee proposals, executive summaries, sales-support materials, RFPs, RFIs, security questionnaires, and due-diligence responses
- Coordinate pricing with Sales, Finance, Operations, and service-line leaders
- Review discounts, concessions, assumptions, and nonstandard terms; escalate financial, operational, or contractual risks
- Conduct deal reviews and develop account strategies, stakeholder plans, competitive positioning, meeting plans, and close strategies
- Support objection handling, commercial negotiations, executive alignment, mutual action plans, and next steps
- Improve pipeline quality, forecast confidence, and sales-stage discipline
- Develop sales training, playbooks, discovery guides, presentation templates, proposal tools, battlecards, case studies, and messaging frameworks
- Support sales onboarding and ongoing development
- Partner with Marketing on campaigns, webinars, events, client stories, and sales collateral
- Establish consistent sales-to-delivery handoffs and facilitate transition meetings for complex or strategic clients
- Develop and maintain the end-to-end pre-sales process, dashboards, reporting, win-loss reviews, and performance improvements
Requirements:
- Five or more years of experience in business-to-business sales, managed services, technology services, cybersecurity services, consulting, or a related industry
- Three or more years of experience in pre-sales, solution consulting, sales consulting, sales enablement, or complex deal support
- Experience 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 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
- Strong executive presence and verbal, written, and presentation skills
- Ability to coach sellers and improve sales performance
- Experience working with Sales, Marketing, Finance, Operations, Legal, and Service Delivery
- Strong organizational skills and ability to manage multiple opportunities and competing deadlines
- Comfort working in a growing, geographically distributed, and evolving organization
- Ability to travel approximately 20%–30%
- Preferred: Experience building or transforming a pre-sales function within an MSP
- Preferred: Experience supporting new-client acquisition and existing-client expansion
- Preferred: Experience selling fully managed and co-managed IT services
- Preferred: Experience supporting cybersecurity, cloud, compliance, advisory, or professional services sales
- Preferred: Experience selling into regulated industries
- Preferred: Familiarity with CRM, proposal-management, sales-enablement, and CPQ platforms
- Preferred: Experience developing sales playbooks, proposal libraries, qualification frameworks, and sales-training programs
- Preferred: Experience supporting channel partners, referral partners, or strategic alliances
- Preferred: Bachelor’s degree in business, marketing, communications, information technology, or a related field, or equivalent professional experience
Benefits:
- Competitive pay
- Quarterly Bonuses
- Progressive PTO
- Medical/Dental/Vision/Life/Disability available
- Tax deferred retirement plan with company match
- Career Development and Coaching
- Fun work environment!
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