Senior Enterprise Sales Director – Higher Ed Tech

Oculusit; Oregon; Hybrid; USD 150,000 - 350,000; Full time

Job summary

OculusIT is seeking a Director of Sales who operates as an IC, acting as a hunter and closer to generate new institutional client opportunities. You will own the full sales cycle—from lead generation to contract signature—driving outbound activity, creating targeted lists, and building a robust pipeline in higher-education technology and managed services.

The role requires a proven track record closing multi-million-dollar deals and strong collaboration with marketing to optimize lead quality

Qualifications

• 15+ years of enterprise sales experience in higher-education technology or IT managed services.
• Proven track record generating large volumes of outbound leads and converting them into qualified opportunities.
• Demonstrated success closing high-value managed services deals ($3M–$5M+).
• Strong understanding of higher-ed IT environment and buying behaviors.
• Exceptional communication, discovery, presentation, and negotiation skills.
• Disciplined, organized, and highly self-motivated with strong pipeline-generation habits.

Responsibilities

• Build, manage, and execute a high-velocity outbound lead generation strategy.
• Develop targeted prospect lists across private colleges, community colleges, HBCUs, tribal colleges, and regional universities.
• Lead end-to-end enterprise sales cycles for IT outsourcing, managed services, helpdesk, cybersecurity, ERP/SIS/CRM/LMS support.
• Conduct discovery with Presidents, CIOs, CFOs, IR leaders, and IT staff.
• Deliver solution presentations, ROI analyses, and business cases; negotiate pricing and contracts.
• Maintain consistent CRM hygiene and provide weekly reporting on pipeline health and revenue progression.

Skills

Enterprise sales

Outbound lead gen

Negotiation

CRM forecasting

Stakeholder engagement

Job description

OculusIT is seeking a Director of Sales who operates as an IC, acting as a hunter and closer to generate new institutional client opportunities. You will own the full sales cycle—from lead generation to contract signature—driving outbound activity, creating targeted lists, and building a robust pipeline in higher-education technology and managed services.

The role requires a proven track record closing multi-million-dollar deals and strong collaboration with marketing to optimize lead quality