Vice President, Enterprise Technology Operations

The RealReal•Remote - California, CA

9d•$290,000 - $310,000•Hybrid

About The Position

The RealReal is looking for a Vice President of Enterprise Technical Operations to lead the teams and systems that keep our business running — from core networking and device management to the enterprise applications and AI platforms that power our people. This leader will own technical operations at scale across our corporate, retail, and authentication center locations, drive enterprise AI enablement, and build a high-performing organization that attracts and grows top talent.

Requirements

10+ years of progressive technical operations leadership, including experience running enterprise IT/infrastructure at scale in a multi-site environment (retail, distribution, or similar physical footprint a plus)
Demonstrated success leading enterprise AI enablement initiatives — deploying and driving adoption of enterprise AI platforms such as Google Gemini Enterprise, Microsoft Copilot, or similar across a workforce
Deep hands-on knowledge of core networking, endpoint/device management (MDM), and infrastructure supporting distributed retail or field locations
Strong track record managing enterprise applications (NetSuite, Workday, Salesforce, Google Workspace, Okta, or comparable systems) and the vendor/stakeholder relationships that come with them
Proven ability to build and run mature incident and problem management functions, including postmortem discipline and continuous improvement processes
A people-first leadership style with a demonstrated record of attracting, developing, and empowering top talent — you build teams people want to stay on
Experience partnering cross-functionally with Security, Product & Technology, Finance, and Retail Operations leaders
Comfort operating in a fast-paced, evolving environment, balancing hands-on execution with strategic planning
Excellent communication skills, with experience presenting to and influencing executive stakeholders
Bachelor's degree in Computer Science, Information Systems, or related field, or equivalent practical experience
Ability to travel up to 10%

Nice To Haves

Experience with enterprise AI adoption and agentic workflows
Experience in e-commerce or marketplace technology
Experience managing vendor partnerships and budgets

Responsibilities

Own and evolve TRR's technical operations strategy across core networking, endpoint/device management, and infrastructure supporting corporate, retail, and authentication center locations
In Partnership with the VP of AI, lead enterprise AI enablement across the organization, driving adoption and governance of enterprise AI platforms such as Google Gemini Enterprise for employee productivity and workflow automation
Direct enterprise application support and roadmap for NetSuite, Workday, Salesforce, Google Workspace, Okta, and related systems, partnering closely with Finance, HR, and Sales/CX stakeholders
Build and mature enterprise incident and problem management practices — from real-time response and escalation to root-cause analysis and prevention — to minimize business disruption
Ensure reliable, secure, and scalable infrastructure and connectivity for retail stores and authentication centers, where operational uptime directly impacts customer and consignor experience
Partner with Product & Technology leadership to align technical operations with broader enterprise architecture and AI platform strategy
Set and manage SLAs, operational metrics, and vendor relationships across managed services, telecom, and SaaS providers
Attract, hire, develop, and retain a high-performing technical operations team; build clear career paths and a culture of ownership and continuous improvement
Drive automation and self-service across IT operations to reduce manual toil and free the team to focus on higher-value, strategic work
Serve as an escalation point and trusted advisor to executive stakeholders on technology operations, risk, and resilience