Director of Sales

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

At OculusIT, we help colleges and universities use technology to operate with confidence, serve their communities, and build a better future. Our work supports the systems higher education depends on every day — from cybersecurity, cloud, and infrastructure to ERP, data, and managed services.

We’re looking for people who want their work to matter, who take ownership, solve problems with clarity, and bring a team-first mindset to complex technology environments. If you’re energized by meaningful work, continuous learning, and serving institutions with purpose, you’ll find a strong fit here.

As a global organization, our values guide how we work:

• Trust is Built Through Action — We communicate openly, follow through, and earn trust through reliability.
• We Own What We Do — We take responsibility for outcomes and stay with problems until they’re solved.
• Distill Clarity from Complexity — We make complicated challenges easier to understand, decide, and act on.
• The Power of We — We collaborate across teams, roles, and perspectives to create better solutions.
• Stay Ahead Always — We stay curious, keep learning, and apply new ideas to improve how we serve.
• Work With Empathy — We listen, respect context, and remember there are people behind every system and decision.

If this sounds like the way you want to work, we’d be excited to meet you.

Job Summary:

The Director of Sales working as an IC, is a pure hunter and closer responsible for generating new opportunities through proactive outreach, advancing qualified deals through the pipeline, and closing new institutional clients. This role requires a self-driven, high-output sales leader who thrives on outbound activity, creative prospecting, and disciplined follow-up. You will own the full sales cycle—from lead generation to contract signature.

Key Responsibilities:

1. New Logo Acquisition & Lead Generation:

• Build, manage, and execute a high-velocity outbound lead generation strategy, including email, LinkedIn, phone outreach, webinars, and event follow-up.
• Develop targeted prospect lists across private colleges, community colleges, HBCUs, tribal colleges, and regional universities.
• Run personalized outreach campaigns using sequences, messaging frameworks, and value-based hooks.
• Source new opportunities through research, digital intelligence, competitor displacement, and cold outreach.
• Consistently exceed weekly and monthly lead-gen KPIs (emails, calls, meetings booked, new opportunities created).
• Collaborate with Marketing to optimize lead quality, but own 70–80% of pipeline creation independently.
• Lead end-to-end enterprise sales cycles for:
• IT outsourcing & managed services
• Helpdesk and student support
• Cybersecurity & SOC services
• ERP/SIS/CRM/LMS support
• Institutional reporting & analytics
• Conduct discovery with Presidents, CIOs, CFOs, IR leaders, and IT staff.
• Deliver solution presentations, ROI analysis, and business cases.
• Negotiate pricing, terms, and contracts.
• Achieve and exceed new-logo revenue goals.

3. Market Development & Territory Ownership:

• Build a territory plan focused entirely on new business generation.
• Create demand in new regions, institution segments, and consortia markets.
• Attend conferences and events to drive booth traffic and post-event leads.

4. Reporting & Forecasting:

• Maintain consistent CRM hygiene and accurate forecasting of all opportunities.
• Provide weekly reporting on lead generation activity, pipeline health, and revenue progression.
• Track metrics related to outbound prospecting, meetings held, and proposals delivered.

Requirements:

Qualifications Required:

• 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.

Preferred:

• Experience selling into small private colleges and community colleges.
• Familiarity with SIS, CRM, LMS, cybersecurity services, cloud hosting, and institutional reporting.
• Existing network of higher-ed presidents, CIOs, CFOs, or cabinet leaders.

Success Indicators:

• High weekly outbound activity and consistent meeting generation.
• Strong pipeline sourced directly from personal lead-gen efforts.
• Achievement of quarterly and annual new-logo quotas.
• Increased penetration in new states and institution segments.