Director of IT

Job Description

Job Description

About Highland Mortgage

Highland Mortgage is a trusted name in residential lending, dedicated to helping families achieve their homeownership goals. We pride ourselves on a culture of integrity, collaboration, and professional growth. As we continue to expand, we are looking for talented individuals who share our commitment to excellence in every transaction.

As part of the Boxcar family of companies — Highland Mortgage, Valor Home Loans, and Vybe Lending — we combine the service of a local lender with a technology-first approach, including proprietary platforms we build and maintain in-house.

Position Overview

We are seeking a hands-on Director of Information Technology to lead IT operations across all Boxcar companies. This role owns the day-to-day reliability, security, and support of our technology environment, leads a small team of IT professionals, and partners closely with the Chief Information Officer and business units to keep a fast-moving, multi-entity lending operation running smoothly. Our environment is built on Microsoft 365, and we are actively developing proprietary technology — so the ability to learn new systems quickly and master them is essential.

This is an operations-focused leadership role. The Director executes and maintains our security and compliance controls in support of the information security program owned by the Chief Information Officer, who serves as the organization's designated Qualified Individual under the FTC Safeguards Rule.

Organizational Expectations

All employees are expected to adhere to organizational policies and procedures, maintain a positive and respectful attitude, communicate regularly with their supervisor, demonstrate flexible and efficient time management, consistently report to work on time, meet department productivity standards, and maintain confidentiality regarding Highland Mortgage, its business, and the affairs of its customers.

Key Responsibilities

• Lead IT operations across all Boxcar companies (Highland, Valor, Vybe), ensuring systems, identity, endpoints, and support are reliable and secure.
• Manage, mentor, and develop a team of 2–3 IT professionals; own help desk and end-user support standards, ticket SLAs, and escalation.
• Administer and optimize the Microsoft 365 environment (Exchange Online, Teams, SharePoint, OneDrive) and Microsoft Entra ID identity and access management.
• Execute and maintain security controls in support of the CIO-owned information security program: endpoint protection, email security, phishing and business-email-compromise defense, MFA/conditional access, and data protection for nonpublic personal information (NPI).
• Support wire-fraud and closing-fund-protection controls in coordination with operations and compliance — a critical risk area in mortgage lending.
• Own business continuity and disaster recovery for IT systems so the business can continue operating through closings and outages.
• Manage vendor and third-party relationships and integrations across the mortgage technology stack; oversee IT procurement and spend against budget.
• Provide cross-department support for user provisioning/deprovisioning and basic administration within departmental line-of-business systems.
• Support internal, investor, and regulatory audits/exams and cyber-insurance requirements; participate in incident response.
• Partner with the CIO and development teams to support and administer proprietary, internally-built platforms.
• Provide reasonable after-hours and on-call availability to support extended lending hours and weekend closings.

Qualifications and ExperienceRequired

• 2+ years of IT management/leadership experience.
• Proven experience administering a Microsoft 365 environment.
• Proficiency with Microsoft Entra ID (formerly Azure AD) for identity, access, and conditional access. Exceptions may be made for candidates with a strong Google Workspace (or comparable IAM) background.
• Strong written and verbal communication skills, with the ability to work across technical and non-technical teams.
• Demonstrated ability to learn and master new systems quickly.
• Experience managing IT security, endpoint management, and end-user support.

Any equivalent combination of education, experience, and training that provides the required knowledge, skills, and abilities may be considered.

Preferred

• Experience in the mortgage industry or another regulated financial-services environment.
• Familiarity with loan origination systems (LOS) — MeridianLink Mortgage a plus — and mortgage point-of-sale (POS) platforms.
• Working knowledge of the broader mortgage tech stack: pricing engines / PPE (e.g., Optimal Blue, Polly), AUS (DU/LPA), e-close / e-sign (e.g., DocuSign, Snapdocs), and CRM (e.g., Total Expert, Surefire).
• Understanding of GLBA / FTC Safeguards Rule obligations and financial-services compliance.
• Relevant certifications: Microsoft SC-300, Azure certifications, CISSP or CISM, ITIL.
• Bachelor's degree in Information Technology, Computer Science, or a related field — or equivalent experience.

What We Offer

• Competitive salary
• Comprehensive health, dental, and vision insurance.
• 401(k) retirement plan.
• Paid time off (PTO) and paid holidays.
• A technology-first, collaborative culture with the opportunity to shape IT across a growing, multi-entity lending organization.