Managing Director - IT Managed Services

Cayuse Holdings

5h•$180,000 - $220,000•Remote

About The Position

The Managing Director of IT Managed Services is a dynamic, entrepreneurial leader responsible for selling, launching, and scaling a high-growth line of business. This is a hybrid role that combines the rapid innovation cycle and agility of a tech startup with operational excellence and revenue generation targets. The leader will drive business development from lead generation to deal closure, champion the creation of new service offerings, and manage global operations. Challenges of the Role Market Credibility: Cultivating high-value client relationships and partnerships with limited past performance in new markets. Balancing Act: Juggling the demands of innovation and sales with the need for rapid iteration and stable 24/7 operations. Resource Scarcity: Operating with lean resources typical of a startup environment, requiring creativity, prioritization, and resourcefulness. Rapid Scaling: Building processes and teams that can scale quickly as new business is captured, often requiring constant adjustment to infrastructure and workflows. Market Volatility: Quickly adapting to evolving client needs and technology shifts in a competitive managed services market. This position aligns with Cayuse’s core values of Innovation, Excellence, Collaboration, Adaptability, and Integrity by fostering technical solutions that meet customer needs, promoting teamwork, and prioritizing quality in deliverables.

Requirements

Bachelor's degree in Computer Science, Information Technology, Business, or a related field, or equivalent work experience. MBA is a plus.
7+ years of experience in IT managed services or IT outsourcing, with at least 3 years in a leadership role.
Strong understanding of IT managed services including one or more of the following: application management, data management, network management, infrastructure (LAN/WAN), cybersecurity, and monitoring tools & services.
Familiarity with emerging technologies like AIOps, cloud monitoring, and automation scripting.
Proven track record in B2B sales, business development, or pre-sales engineering related to IT services or managed services is essential.
Experience managing global or geographically dispersed teams (onshore/offshore).
Must be able to pass a background check. May require additional background checks as required by projects and/or clients at any time during employment.
Must possess problem-solving skills.
Ability to respond effectively to customers with a sense of urgency.
Proficient in Microsoft and Adobe toolsets, including Excel, Word, PowerPoint, Acrobat, etc.
Highly motivated with the ability to handle and manage multiple tasks at any one time.
Ability to forge new relationships, individual and teaming in nature.
Must be a Self-starter, that can work independently and as part of a team.
Exceptional leadership, entrepreneurial spirit, and a proactive "owner" mindset.
Superior communication, presentation, negotiation, and client-facing skills.
Ability to thrive in ambiguity and drive clarity in a fast-paced, high-pressure environment.

Nice To Haves

Experience in startups, greenfield programs, or new services launch is highly desirable.

Responsibilities

Product Innovation: Define the vision and roadmap for new IT Managed Service offerings (e.g., DevOps, AIOps, application management, specialized cloud monitoring services, etc.), from ideation and MVP (Minimum Viable Product) development to full market launch.
Market Validation: Conduct market research, competitive analysis, and client feedback loops to ensure market fit for new and existing services.
Agile Development: Lead agile development cycles for new service features and operational enhancements, embracing rapid iteration and a "fail fast, learn faster" mindset.
Proof of Concept (POC) Management: Manage and execute POCs with lighthouse customers to validate new offerings and refine service delivery with initial clients.
Tech Stack Selection: Drive the selection and implementation of new, cutting-edge monitoring and automation technologies to support innovative offerings and enhance efficiency.
Revenue Generation: Drive growth as a distinct line of business by achieving assigned sales targets and increasing annual recurring revenue from IT Managed Services.
Sales Pipeline & Lead Generation: Generate new leads from existing and new relationships. Build and manage a robust sales pipeline in collaboration with the core sales and marketing teams. Create sales plans and forecasts to meet company objectives.
RFP Management: Lead the technical and operational response to Requests for Proposal (RFPs), ensuring compelling, accurate, and competitive proposals are submitted.
Deal Closure: Provide expert technical support during the sales cycle, conducting client presentations, demonstrating service capabilities, and leading technical negotiations to successfully close deals.
Lead, mentor, and develop high-performing, agile teams capable of both stable operations and rapid innovation.
Define and execute a strategy for building and leveraging both onshore and offshore teams, optimizing for cost efficiency, 24/7 coverage, and specialized skill sets within a lean operational model.
Oversee daily BD and client delivery within a fast-paced environment, ensuring scope, schedule, and quality adherence and alignment with SLAs.
Manage end-to-end service delivery for a diverse client base. Maintain high customer satisfaction levels.
Other duties as assigned.