Director, Information Technology - Insurance Industry

Upland Capital Group, Inc. is an AM Best rated “A-” VIII specialty property/casualty insurer headquartered in Dallas, Texas. Through its wholly owned insurance carrier, Upland Specialty Insurance Company, the company markets, underwrites and services specialty insurance products in select markets to include excess transportation, construction casualty, excess casualty, primary general liability, excess public entity, professional liability errors and omissions as well as excess cyber liability.

We focus on “old school” underwriting as a craft, add “new school” analytics and technology, and encourage a gritty, growth mindset among people called “we entrepreneurs.”

As an Excess and Surplus (E&S) carrier, we face unique and interesting challenges every day. We are seeking a Director, Information Technology to join our team; candidates must be able to work Eastern or Central Standard Time Hours.

Primary Function:

The Director of IT is accountable for the strategy, delivery, and continuous improvement of enterprise IT services with a primary emphasis on IT Support, asset management, identity and access management (IAM), SaaS/application administration, and third-party service delivery. This role leads IT service management practices (ITSM) practices, oversees Managed Service Providers (MSPs) and key vendors, and ensures high-quality secure, and compliant IT operations aligned to business objectives.

The Director will overhaul and own operational excellence across the IT support ecosystem including incident/problem management, employee lifecycle enablement (onboarding/offboarding), asset lifecycle, and the optimization of cloud and application spend. The role partners closely with Security Operations, with Upland’s distributed IT staff across multiple departments, and business leaders to drive adoption of enterprise-grade technologies, strengthen security controls (including SSO and identity federation), and deliver a consistently exceptional end‑user experience.

This leader sets standards, establishes repeatable processes, and communicates clearly, producing and maintaining high-quality technical documentation and executive‑ready materials that improve reliability, auditability, and stakeholder confidence.

Duties and Responsibilities of our Director of IT:

• Establish measurable service outcomes (SLA attainment, first‑contact resolution) and lead continuous improvement initiatives
• Define, develop, and deploy an overhaul to the IT Service Desk and Desktop Support operations to improve user experience, operational efficiency, and support scalability
• Analyze support trends and metrics to identify opportunities for automation, self‑service, and process optimization
• Oversee onboarding/offboarding, device provisioning, device patching, and hardware/software lifecycle processes to ensure speed, consistency, and control
• Build and maintain strong cross‑functional partnerships with Security, Technology, Operations, HR, and business leaders to align priorities and ensure service readiness
• Lead MSP and vendor performance management, including SLA/KPI governance, quarterly business reviews, and remediation plans as needed
• Own vendor contracts, renewals, licensing, and subscription management to ensure uninterrupted service delivery and favorable commercial outcomes
• Lead IAM Operations and improvements, including SSO implementations, identity federation, role‑based access, and access governance
• Own active management of cloud spending and application/licensing spend, partnering with Finance to improve transparency, forecasting, and cost governance
• Provide regular executive reporting on spend drivers, optimization initiatives, and realized savings
• Partner with Security Operations to enforce endpoint and application security controls, including patching, device compliance, and secure configuration baselines
• Support vulnerability remediation and compliance with applicable frameworks and regulatory requirements (e.g., SOX, GDPR, as applicable)
• Develop and maintain high‑quality technical documentation, including IT standards, policies, runbooks, SOPs, knowledge articles, and onboarding/offboarding guides
• Serve as the primary escalation point for complex IT issues, ensuring rapid resolution and minimal business disruption
• Conduct quarterly users access reviews for in‑scope systems, and support audit compliance and monitoring
• Serve as the application administrator for enterprise applications not supported or managed by the MSP provider, ensuring proper configuration, access control, and operational continuity
• Support annual IT forecasting budget

Experience, Education, Special Skills Required from our Director, Information Technology:

• Bachelor’s degree and/or Master’s Degree in Information Systems, Computer Science, Business or a related discipline (or equivalent experience)
• 5-8 years progressive IT experience, including leadership in enterprise IT Operations and support functions
• Experience in insurance or regulated financial services strongly preferred; familiarity with non‑admitted carriers a plus
• Expertise in Jira Service Management
• Strong expertise in Microsoft Entra ID (Azure AD) and modern identity patterns (SSO, federation, MFA)
• Working knowledge of cloud architectures, cloud networking concepts, and cloud security principles
• Familiarity with ITSM tooling and ITIL practices; ITIL certification preferred
• Experience operating within Agile environments and partnering effectively with engineering and security teams
• High attention to detail and quality; consistently produces accurate work products suitable for audits and executive review
• Strong analytical and problem‑solving skills
• Demonstrated experience in providing technical support
• Comfort with leading multiple tasks and projects simultaneously, prioritize decisions and tasks effectively, and thrive in a fast‑paced, dynamic environment
• Proven ability to be proactive and highly effective in a fully‑remote environment

Disclosures:

Pay Estimate: $150,000 - $170,000 / year

Other compensation: annual incentive program

Benefits: health insurance including FSA and HSA options and free access to Teladoc, vision, dental, disability and life insurance, parental leave, responsible time off (unlimited vacation days without an accrual system), paid sick time as required by law, 401(k), tuition reimbursement and employee assistance program.

Anticipated close date: 1/30/2026