Director of Technology & Operations (Path to VP / CTO)

GEM Technologies is a full-service managed IT service provider delivering strategic technology solutions that empower businesses to grow securely and efficiently. With offices in NYC and Fort Myers and a relentless focus on personalized service and innovative IT solutions, we help our clients solve complex technology challenges, optimize performance, and enhance cybersecurity.

Position Title: Director of Technology & Operations

Reports to: President
Location: Remote / Hybrid (as applicable)

Role Summary

We are seeking a senior technology and operations leader to help scale and mature our Managed Services Provider. This role will serve as the operational and technical backbone of the organization—owning technology strategy, team leadership, service delivery excellence, and continuous improvement initiatives.

The Director of Technology & Operations will partner closely with the President to translate vision into execution, while taking full ownership of day-to-day technical leadership, people management, and operational rigor.

Key Responsibilities

Technology Leadership & Strategy

• Define and execute the company’s technology strategy aligned with business goals and the evolving cybersecurity landscape
• Evaluate emerging technologies, tools, and platforms to maintain competitive advantage
• Oversee core MSP platforms (Microsoft 365, security stack, RMM, PSA, backups, networking, etc.)
• Ensure strong cybersecurity standards across internal systems and client environments
• Act as senior technical authority in client-facing discussions when needed

Operational Excellence

• Standardize and optimize service delivery processes, documentation, and recurring task checklists
• Own continuous improvement initiatives across service operations
• Partner with leadership on capacity planning and resource utilization
• Ensure high-quality, consistent client experience across the MSP

People Leadership

• Lead, mentor, and develop the technical team
• Conduct regular one-on-ones, performance reviews, and feedback cycles
• Oversee hiring and interviewing of employees and contractors
• Develop and maintain technical and behavioral pre-employment assessments
• Foster a culture of accountability, learning, and operational maturity

Service Delivery & Client Engagement

• Oversee development of Quarterly Business Reviews (QBRs)
• Support key client relationships and escalation management
• Translate client business needs into scalable technical solutions
• Ensure service quality metrics and SLAs are met or exceeded

Administrative & Financial Oversight

• Review employee and subcontractor timesheets
• Oversee subcontractor management, approvals, and coordination with billing
• Support billing and invoicing processes in coordination with finance/admin staff

Why This Role Is Unique

• Hybrid remote - travel to client and other locations are on an as needed basis (normally you will work from your home office)
• Direct influence on company direction and growth
• High autonomy and trust
• Opportunity to shape a modern, security-first MSP
• Clear pathway to expanded executive leadership as the company scales

Requirements

Experience

• 8–15 years in IT, MSP, or technology services
• Prior leadership experience in an MSP or services-based IT organization
• Strong background in Microsoft ecosystems, cybersecurity, and modern IT stacks
• Proven ability to scale teams and improve operational maturity

Leadership Style

• Strategic thinker who is also execution-oriented
• Calm under pressure, structured, and process-driven
• Trusted mentor and people leader
• Comfortable acting as “second-in-command” to the owner

Benefits

• Health insurance
• Dental/Vision insurance

• 4 weeks PTO
• Flexible / remote-first culture
• Clear authority
• Professional development budget and paid certifications
• Conference attendance (MSP-specific)

In compliance with the state and city salary transparency requirements, the potential salary for this position is from $150,000 to $175,000 which represents a range commensurate with experience. Anticipated bonus potential for this position is 10-15%

Visa sponsorship for this role is currently not available.