Director of Pre-Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Develop and uphold a structured methodology for discovering new sales opportunities.

• Lead or assist in discovery discussions with business leaders, executives, IT stakeholders, operations teams, and procurement.

• Identify business goals, challenges, operational pain points, growth strategies, cybersecurity and compliance issues, service expectations, budget considerations, decision criteria, key stakeholders, and desired outcomes.

• Mentor the sales team on effective discovery questioning and identifying client needs.

• Convert discovery findings into opportunity strategies and client value propositions.

• Accurately and consistently document discovery information in the CRM.

• Create sales narratives that align CompassMSP’s managed IT, cybersecurity, cloud, compliance, strategic advisory, and professional services with client priorities.

• Collaborate with technical, operational, security, and service-delivery experts.

• Lead or assist in 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 any financial, operational, or contractual risks.

• Conduct deal reviews and formulate account strategies, stakeholder plans, competitive positioning, meeting plans, and closing strategies.

• Aid in objection handling, commercial negotiations, executive alignment, mutual action plans, and next steps.

• Enhance pipeline quality, forecast confidence, and sales-stage discipline.

• Develop sales training materials, playbooks, discovery guides, presentation templates, proposal tools, battlecards, case studies, and messaging frameworks.

• Support sales onboarding and continuous development.

• Collaborate with Marketing on campaigns, webinars, events, client stories, and sales materials.

• Establish consistent sales-to-delivery transitions and facilitate meetings for complex or strategic clients.

• Create and maintain the comprehensive pre-sales process, dashboards, reporting, win-loss analyses, and performance enhancements.

⛳️ Requirements

• Minimum of five years of experience in business-to-business sales, managed services, technology services, cybersecurity services, consulting, or a similar field.

• At least three years of experience in pre-sales, solution consulting, sales consulting, sales enablement, or complex deal support.

• Proven experience in managing complex, multi-stakeholder sales cycles.

• Strong grasp of consultative and value-based selling techniques.

• Experience in leading discovery sessions, presentations, proposal reviews, demonstrations, and executive discussions.

• Familiarity with coordinating proposals, RFP responses, pricing, and internal approvals.

• Strong commercial acumen and understanding of recurring-revenue sales.

• Ability to articulate technology and service concepts into clear business value.

• Strong executive presence along with excellent verbal, written, and presentation skills.

• Capability to coach sales personnel and enhance sales performance.

• Experience collaborating with Sales, Marketing, Finance, Operations, Legal, and Service Delivery teams.

• Excellent organizational skills and ability to handle multiple opportunities and competing deadlines.

• Comfortable working in a growing, geographically diverse, and dynamic organization.

• Willingness to travel approximately 20%–30%.

• Preferred: Experience in building or transforming a pre-sales function within an MSP.

• Preferred: Experience in supporting new-client acquisition and existing-client expansion.

• Preferred: Experience in selling fully managed and co-managed IT services.

• Preferred: Experience in supporting cybersecurity, cloud, compliance, advisory, or professional services sales.

• Preferred: Experience in selling into regulated industries.

• Preferred: Familiarity with CRM, proposal management, sales enablement, and CPQ platforms.

• Preferred: Experience in creating sales playbooks, proposal libraries, qualification frameworks, and sales training programs.

• Preferred: Experience in 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 salary.

• Quarterly bonuses.

• Progressive paid time off.

• Medical, dental, vision, life, and disability insurance available.

• Tax-deferred retirement plan with company match.

• Opportunities for career development and coaching.

• Enjoyable work environment!