VP, Enterprise Systems & Helpdesk IT

Comply • Washington, DC

15d • Onsite

About The Position

Comply is seeking a hands-on, execution-oriented VP, Enterprise Systems & Helpdesk IT to serve as the technical architect and operational leader of our internal enterprise systems, AI platforms, and global IT Service Desk.
This leader will own the architecture, integrations, governance, and operational excellence of Comply’s internal SaaS ecosystem — including Salesforce, NetSuite, Jira/Confluence, Gainsight, GuideCX, Tableau, Rippling, Microsoft 365, Mimecast, and other core platforms — while also defining and leading our internal AI systems strategy.
Operating in a co-ownership model, this leader will partner closely with functional executives (e.g., CFO as business owner of NetSuite; CRO as business owner of Salesforce and Gainsight) to translate business priorities into scalable, secure, and future-ready technical solutions. In addition, this role will own enterprise AI use cases across corporate data, reporting, and analytics — ensuring responsible governance and measurable business impact.
This role is based onsite in Arlington, VA.

Requirements

• Bachelor’s degree in Computer Science, Information Systems, Engineering, Business, or equivalent experience.
• 10+ years of progressive IT experience, including 5+ years in leadership roles overseeing enterprise systems, integrations, and service delivery within distributed environments.
• Demonstrated hands-on expertise designing and operating enterprise SaaS ecosystems, with deep experience in Salesforce and NetSuite.
• Proven experience leading system integrations, data pipelines, enterprise reporting, and governance frameworks.
• Experience implementing and governing enterprise AI solutions, including generative AI tools, AI-enabled automation, or advanced analytics use cases within corporate systems.
• Strong understanding of AI data governance, model risk management, and responsible AI practices.
• Experience partnering with executive business leaders in a co-ownership model for enterprise systems.
• Track record of building and leading a high-performing global IT Service Desk organization.
• Strong vendor management, contract negotiation, procurement, and IT financial management experience.
• Experience implementing security and compliance controls in collaboration with security teams.
• Excellent executive communication and cross-functional leadership skills.
• Must be located in the Washington, DC area and able to work onsite in Arlington, VA.

Nice To Haves

• Advanced degree (MS, MBA) or relevant certifications (Salesforce, NetSuite, ITIL, PMP, CISSP) is a plus.
• Experience in a high-growth SaaS environment, including scaling systems through organic growth and M&A is a plus.
• Experience establishing or leading an enterprise AI strategy or AI Center of Excellence is a plus.
• Deep expertise in identity and access management (SSO, SAML/OAuth), BI best practices (Tableau or equivalent), and modern endpoint/MDM tooling is a plus.
• Familiarity with modern AI architectures (LLM integrations, RAG frameworks, API-based AI services) applied to corporate knowledge systems and analytics is a plus.

Responsibilities

• Serve as chief architect for Comply’s enterprise SaaS landscape, owning system design, integrations, data models, release management, and lifecycle governance.
• Architect and maintain reliable integrations and data pipelines (iPaaS and custom) to ensure data integrity, automation, and cross-system reporting.
• Establish enterprise data governance standards, access controls, and reporting frameworks.
• Lead corporate technology roadmap planning, prioritization, implementation, and retirement decisions across business units.
• Own Comply’s internal AI systems strategy, including generative AI tools, AI-enabled automation, and embedded AI capabilities within enterprise platforms.
• Identify, prioritize, and implement high-impact AI use cases across Finance, Sales, Customer Success, HR, and Operations — leveraging enterprise data to improve forecasting, reporting, analytics, and workflow efficiency.
• Architect AI-enabled reporting and analytics capabilities, including predictive insights, anomaly detection, and natural-language querying across corporate datasets.
• Establish AI governance frameworks covering data classification, PII protection, access controls, model risk, auditability, and regulatory alignment (SOC 2, GDPR, etc.) in partnership with the CISO.
• Evaluate and manage enterprise AI vendors and platforms; drive responsible adoption and measurable ROI.
• Lead the global IT Service Desk supporting 350+ distributed employees.
• Define and manage SLAs, ticket workflows, escalation paths, knowledge-base governance, and performance metrics.
• Provide hands-on escalation leadership to ensure high-quality end-user support and operational reliability.
• Maintain business continuity and disaster recovery plans for critical systems; lead IT incident response.
• Partner with the CISO to implement and enforce enterprise security controls (SSO/MFA, least-privilege access, logging/monitoring).
• Own corporate IT vendor relationships, contract negotiation, budgeting, forecasting, and spend optimization.
• Provide clear executive reporting on IT health, AI adoption, roadmap progress, risks, and KPIs.
• Serve as the technical counterparty to business application owners, ensuring alignment between system capabilities and business objectives.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive