Job Description

About N2N

N2N Services is entering its 15th year with bold momentum. Our Illuminate integration platform connects 500+ colleges, and our new LightLeapAI platform is already powering fraud detection, student success, and AI-driven innovation across 100+ Community Colleges nationwide with rapid expansion underway.

Were preparing for significant growth, scaling our AI solutions nationally, and laying the groundwork for a massive transformation. To support this evolution, were hiring a Chief of Staff to help strengthen our operations, elevate our teams, and drive disciplined execution across the company.

The Role

As Chief of Staff, youll work directly with our CEO as a strategic partner, operational leader, and cross-functional integrator. This role is for someone who thrives in high-growth environments, brings structure to complexity, and can translate ambitious goals into clear, trackable execution.

Youll help drive accountability, unify teams, sharpen communication, and ensure that N2N operates with clarity, speed, and discipline as we scale.

What You Are Expected to Do

Strategic Planning & Alignment

• Translate company strategy into OKRs, execution plans, and measurable outcomes.
• Lead quarterly and annual planning processes.
• Bring alignment, transparency, and cadence across product, engineering, PMO, sales, and operations.

Operational Excellence

• Build frameworks, dashboards, and processes that improve efficiency and accountability.
• Drive key initiatives, including LightLeapAIs national rollout and enterprise integration programs.
• Standardize documentation, reporting, and internal communication.

Team & Leadership Support

• Help develop managers and emerging leaders through coaching, clarity, and structured follow-up.
• Support performance reviews, professional development plans, and organizational design.
• Identify operational gaps and ensure theyre addressed quickly.

CEO Enablement

• Prioritize and streamline decision-making across the executive team.
• Prepare materials for board meetings, investors, partners, and major proposals.
• Ensure critical initiatives remain on track and deliver results.

What You Bring

• 912+ years in strategy, operations, consulting, product, PMO, or Chief of Staff roles.
• Experience in SaaS, AI, EdTech, or enterprise software required.
• Experience managing teams that include onsite resources, offshore resources, consultants, and WFH resources.
• Ability to bring order, clarity, and structure to fast-changing environments.
• Excellent communication and writing skills especially with executive-level audiences, investors, and board members.
• Strong emotional intelligence balanced with the confidence to hold teams accountable.
• Ability to operate at both 30,000 feet and ground level within the same day.

Why Join Us?

Youll be stepping into a pivotal moment for N2N.

Were scaling AI-powered platforms that will define the future of higher education, fraud detection, and enterprise applications. This role gives you a front-row seat and real influence in shaping the next phase of our growth.

If you want to help build a disciplined, high-performing organization with a clear mission and extraordinary potential, wed love to meet you.

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