CompassMSP Logo

CompassMSP

Director of Pre-Sales

Posted 15 Days Ago
Be an Early Applicant
Remote
Hiring Remotely in United States
Senior level
Remote
Hiring Remotely in United States
Senior level
Leads pre-sales strategy for managed IT, cybersecurity, cloud, compliance, and advisory services. Develops discovery methodologies, supports complex sales cycles, leads presentations and demonstrations, coordinates proposals, RFPs, pricing, and approvals, and ensures effective sales-to-delivery handoffs. Coaches sellers, manages sales enablement, improves deal execution, translates technical solutions into business value, and collaborates with technical, operational, legal, finance, and service-delivery teams.
The summary above was generated by AI
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!

Similar Jobs

14 Minutes Ago
Remote or Hybrid
Northbrook, IL, USA
85K-147K Annually
Senior level
85K-147K Annually
Senior level
Automotive • Professional Services • Software • Consulting • Energy • Chemical • Renewable Energy
Manage and grow customer accounts by selling UL Solutions testing services, developing sales pipelines, identifying opportunities, conducting discovery, preparing proposals, and closing deals. Build client relationships, support renewals, collaborate with engineering, operations, product management, and marketing, and provide industry insights. The role includes account planning, executive presentations, trade-show participation, and up to 25% domestic travel.
Top Skills: Crm SoftwareExcelMS OfficeOutlookPowerPointWord
49 Minutes Ago
Remote or Hybrid
USA
Mid level
Mid level
Machine Learning • Payments • Security • Software • Financial Services
Leads system monitoring, maintenance, incident response, troubleshooting, reliability improvements, patching, upgrades, and production support. Analyzes root causes, tracks availability and performance metrics, coordinates system changes, and supports application governance, continuity testing, audits, and regulatory inquiries. Coaches junior staff and ensures supported systems comply with technology standards and risk-management requirements.
Top Skills: Application Programming Interfaces (Apis)Genesys CcpulseIt Service Management (Itsm)
2 Hours Ago
Remote or Hybrid
United States
145K-196K Annually
Senior level
145K-196K Annually
Senior level
Artificial Intelligence • Cloud • Information Technology • Sales • Security • Software • Cybersecurity
Manage and mentor Product Managers while guiding product strategy, prioritization, roadmap execution, and lifecycle management for Rapid7’s cybersecurity platform. Partner with Product, Engineering, UX, executives, customers, and cloud ecosystem partners to define requirements, launch features, analyze usage and feedback, and drive market impact. The role also promotes AI-enabled product management practices, customer-centric decision-making, cross-functional alignment, and development of high-performing global teams.
Top Skills: Artificial IntelligenceCloud SecurityVulnerability Management

What you need to know about the Chicago Tech Scene

With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.

Key Facts About Chicago Tech

  • Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
  • Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
  • Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
  • Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
  • Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
  • Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory

Sign up now Access later

Create Free Account

Please log in or sign up to report this job.

Create Free Account