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. 

• Five or more years of experience in business-to-business sales, managed services, technology services, cybersecurity services, consulting, or a related industry.

• Three + years of experience in pre-sales, solution consulting, sales consulting, sales enablement, or complex deal support.
• Experience working within an MSP, MSSP, IT-services, cybersecurity-services, telecom, cloud-services, or recurring-revenue businesses highly desired
• 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 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.
• 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 20%–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-servicessales.
• Experience selling into regulated industries such as healthcare, financial services, legal, manufacturing, construction, or government contracting.

• Familiarity with CRM,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 relatedfield, or equivalent professional experience.

• 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.
• Ensure discovery conversations identify:
  • Business objectives
  • Current challenges
  • Operational pain points
  • Growth plans
  • Cybersecurity and compliance concerns
  • Service expectations
  • Budget considerations
  • Decision criteria
  • Key stakeholders
  • Desired business outcomes

• 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.

Solution Positioning 

• Develop compelling sales narratives that connect CompassMSP’s services to the client’s business priorities.
• 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.
• Prevent sales commitments that are unclear, unsupported, or inconsistent with CompassMSP’s delivery model.
• Help differentiate CompassMSP from competitors based on service quality, security, responsiveness, strategic guidance, client experience, and business impact.

Sales Presentations and Demonstrations 

• Lead and/or support executive presentations, discovery workshops, proposal reviews, demonstrations, and finalist meetings.
• Prepare sellers and internal subject-matter experts for important client interactions.
• Develop clear presentation strategies based on the audience, opportunity stage, client priorities, and competitive environment.
• Ensure presentations are concise, relevant, persuasive, and focused on client outcomes.
• Facilitate meetings that include both business and technical stakeholders while keeping conversations commercially focused.
• Anticipate client questions and objections and prepare effective responses.
• Coach team members on presentation skills, storytelling, meeting facilitation, and executive communication.
• Participate directly in high-value and strategically important sales opportunities.

Proposal and RFP Management 

• Oversee the development of high-quality proposals, presentations, executive summaries, and sales-support materials.
• Coordinate responses to requests for proposals, requests for information, security questionnaires, and due-diligence requests.
• Ensure proposals accurately reflect the client’s priorities, CompassMSP’s value proposition, agreed services, pricing assumptions, and expected outcomes.
• Improve the consistency, quality, and speed of proposal development.

Pricing and Commercial Coordination 

• Partner with Sales, Finance, Operations, and service-line leaders to coordinate pricing for managed services and related offerings.
• Ensure pricing conversations account for service complexity, client requirements, competitive conditions, implementation needs, and target margins.
• Help sellers understand and communicate the value behind CompassMSP’s pricing.
• Support the development of pricing options, service tiers, bundled offerings, and commercial alternatives.
• Review proposed discounts, concessions, assumptions, and nonstandard terms.
• Escalate opportunities that present unusual financial, operational, or contractual risk.
• Help protect revenue quality and long-term profitability while maintaining a competitive and client-focused sales approach.

Deal Strategy and Sales Execution 

• Conduct structured deal reviews with Account Executives and Sales leadership.
• Help develop account strategies, stakeholder plans, competitive positioning, meeting plans, and close strategies.
• Identify the actions required to move opportunities through the sales process.

• Assist sellers in developing mutual action plans and clear next steps with prospective clients.
• Help navigate complex buying groups involving executives, IT leaders, finance, procurement, legal, security, and operations.
• Support objection handling, commercial negotiations, and executive alignment.
• Identify patterns across stalled, lost, and successful opportunities and use those insights to improve sales execution.
• Partner with Sales leadership to improve pipeline quality, forecast confidence, and stage discipline.

Sales Enablement 

• Develop training and resources that improve seller confidence across CompassMSP’s portfolio.
• Train Account Executives and Channel Sales teams on:
  • Discovery
  • Qualification
  • Value-based selling
  • Service positioning
  • Competitive differentiation
  • Objection handling
  • Proposal presentation
  • Executive communication
  • Business-case development
• Create sales playbooks for priority industries, client types, services, and use cases.
• Build discovery guides, presentation templates, proposal tools, competitive battlecards, case studies, and messaging frameworks.
• Support onboarding and ongoing development for new sales team members.

• Partner with Marketing on campaigns, webinars, events, client stories, and sales collateral.
• Ensure sales teams remain current on changes to CompassMSP’s service portfolio and market positioning.

Sales-to-Delivery Handoff 

• Establish a consistent handoff process from Sales into onboarding, operations, account management, and service delivery.
• Ensure the final agreement reflects what was presented, discussed, priced, and approved during the sales process.
• Confirm that client objectives, expectations, commitments, assumptions, exclusions, and next steps are clearly documented.
• Facilitate internal transition meetings for complex or strategic clients.
• Help resolve discrepancies between sales expectations and delivery requirements before implementation begins.
• Gather feedback from onboarding and service-delivery teams regarding scope clarity, client expectations, and sales-process quality.
• Use delivery feedback to improve future discovery, proposals, pricing coordination, and client communication.

Process and Performance Management 

• Develop and maintain the end-to-end pre-sales process.
• Define clear stages, deliverables, ownership, approval requirements, and response-time expectations.
• Improve CRM documentation, opportunity notes, proposal tracking, and sales-process visibility.
• Establish dashboards and reporting for pre-sales activity and performance.
• Conduct win-loss reviews and identify actionable trends.
• Use data to improve resource allocation, sales effectiveness, proposal quality, and close rates.
• Continuously simplify processes while maintaining appropriate commercial and operational controls.

• 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!