CompassMSP

Strategic IT support to boost profitability

Director of Pre-Sales

Pre-Sales Solution EngineeringConfirmed live in the last 24 hours

Full-timeRemote in USA

About the Job

Requirements

At least 5 years of experience in business-to-business corporate sales.
At least 3 years of experience in pre-sales, solution consulting, sales consulting, sales enablement, or complex deal support.
At least 3 years of experience working within an MSP, MSSP, IT-services, cybersecurity-services, telecom, or another 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.
Experience coaching sellers and improving 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 30%.

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 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 proposed services are aligned with the company's current capabilities and approved offerings.
Vet and prevent sales commitments that are unclear, unsupported, or inconsistent with the company's delivery model.
Serve as a subject-matter expert for sales presentations and demonstrations for high-value sales opportunities.
Develop, coordinate, and lead proposal and RFP management.
Coordinate pricing and commercial matters.
Lead deal strategy and sales execution, including identifying patterns, addressing objections, competitive positioning, and navigating complex buying groups.
Oversee, create, implement, and execute sales enablement.
Manage sales-to-delivery handoff.
Manage process and performance.

Desired 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.
A bachelor's degree in business, marketing, communications, or information technology, or equivalent professional experience.

Role Description

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 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

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.

Compensation & 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!

Salary

Minimum: 135000
Maximum: 150000
Currency: USD
Pay period: Annual

About the Company

CompassMSP

Strategic IT support to boost profitability

CompassMSP provides strategic IT support solutions aimed at improving business efficiency and profitability. It offers two service models: AutoPilot, which leads a company’s technology strategy and operations so leadership can focus on core business activities, and CoPilot, which helps CIOs or IT managers execute their IT vision and initiatives. The approach designs IT infrastructure that supports and automates desired workflows, delivering services through contracts and partnerships. This makes IT align with business goals to reach end goals faster and with higher profits. The company’s goal is to help businesses leverage technology to achieve measurable business outcomes with fewer resources.

Company size: 201-500
Company stage: Not listed
Total funding: Not listed
Headquarters: Hartford, VT
Founded: Not listed

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