Director of Technology

Location: In-office at our New York (Long Island) headquarters preferred. In-office options are also available in Charlotte, North Carolina and Waco, Texas. Hybrid and fully remote arrangements will be considered for the right candidate, with the understanding that limited, periodic travel will be required.

Company Size: 50+ Employees | 800+ Active Clients

Reports To: CEO / Ownership

The Opportunity: Are You a “Unicorn”?

Most “Director” roles ask you to manage people and spreadsheets. Most “Admin” roles ask you to manage servers and tickets. We need someone who does both, and who knows how to scale themselves out of the critical path.

We are looking for a Director of Technology who is a Full-Stack Executive. You will be the senior technical leader for our company, overseeing a distributed workforce of 52 staff members and the integrity, availability, and strategic use of data for over 800 clients. You will manage a team of four specialized Developers and a high-touch Administrative Assistant. You are hands-on when it matters, but your longer-term success is defined by building systems, standards, and teams that reduce friction, minimize escalation, and allow the organization to scale.

You are not “too big” to troubleshoot a leadership member’s home network or jump on a call with an ISP to resolve a circuit outage. You may follow that with a conversation with a school or library client about network topologies and solutions that the E-Rate program can help fund. At the same time, you are always looking forward with a growth and scaling mindset to design the systems of the future.

The Role in Three Dimensions

1. The Architect (Strategy, Cloud, and Data)

You own the roadmap for all technology the company uses. From building technology standards and network designs, to leading our migration from legacy hosting (LiquidWeb) to modern cloud environments (AWS), to architecting and governing our M365 and Zoom ecosystems, you define how we work.

You also oversee and evolve complex ETL processes that transform raw program and operational data into trusted, actionable datasets. Data is a core strategic asset for our firm. You are responsible not only for its security and reliability, but for enabling its use in analytics, dashboards, internal tools, and client-facing insights that differentiate us in the market.

You act as the Principal Architect for our MSSP and other vendors, ensuring their solutions meet our standards rather than being implemented as generic, off-the-shelf deployments.

2. The Manager (People, Vendors, and Leverage)

You lead a four-person AppDev team, acting as their Product Owner, setting priorities, and removing blockers so they can focus on building high-impact tools. You mentor and support a talented Administrative Assistant who handles daily triage, logistics, and first-line coordination.

You are the primary point of contact for our MSSP, multiple ISPs, and cellular carriers, handling complex vendor relationships and escalation paths. Your goal is not to be the bottleneck, but to establish clear ownership models, documentation, and standards that allow issues to be resolved at the right level.

3. The First Responder (Service, Trust, and Stability)

You are the face of technology for our staff and leadership team. You provide white-glove support where it matters most and serve as the final escalation point for complex or sensitive issues.

Whether it is testing a new internal tool, fine-tuning email security rules to reduce false positives, or executing a mass hardware refresh for the entire fleet on a five-year lifecycle, you ensure the business continues to operate smoothly. With your well-developed emotional intelligence, staff understand that when technology fails, they are supported by someone who listens, explains, and follows through.

What Your Typical Week Looks Like

Strategic Pivot: You may start the morning in a high-level budget or planning meeting with leadership and spend the afternoon debugging a specialized internal tool with the AppDev team.

Problem Solving: You assess submitted feature requests for internal software, distinguishing true business needs from nice-to-haves, before they enter the development queue.

Vigilance: You review cybersecurity and operational reports, keeping an eye on our single-pane-of-glass dashboards supporting 7+ office locations.

Direct Impact: You personally handle a time-sensitive technical issue for a staff member or meet with a client’s technology team to discuss network design options aligned with upcoming E-Rate funding cycles.

Grit: You spend focused time resolving issues that fall between vendors, such as SharePoint synchronization problems or internal tool integrations that external providers are not equipped to support, while documenting outcomes to prevent repeat issues.

What You Bring to the Table

The Generalist-Specialist Mindset: Deep experience in M365 Global Administration, Zoom Unified Communications, and AWS cloud architecture, paired with the ability to move fluidly across domains.

Vendor Management Mastery: Proven ability to hold an MSSP accountable, coordinate across multiple vendors, and navigate ISP and carrier support structures effectively.

Hardware and Lifecycle Management: Experience managing procurement, warranties, refresh cycles, and logistics for distributed teams.

Developer Empathy: Strong understanding of the SDLC and developer workflows, with the ability to manage and support standard tooling such as IDEs, repositories, and CI/CD environments.

Networking and E-Rate Knowledge: Solid grounding in modern networking concepts and an understanding of the E-Rate program from the client perspective, enabling informed guidance on eligible services and network design.

Emotional Intelligence: The ability to explain risk, tradeoffs, and technical decisions clearly to non-technical stakeholders and to manage up with confidence and transparency.

Adaptability: Comfort operating in an environment where priorities shift quickly and creative problem-solving is part of the daily work.

Why This Role Is Different

You will not be a cog in a giant machine. You will help design and operate the engine. You will have real autonomy, meaningful decision-making authority, and a leadership team that values technology as a strategic function, not just a support service.