Vice President, Enterprise Technology Operations

About The Role

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.

What You Get To Do Every Day

• 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

What You Bring To The Role

Minimum 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%.

 

Preferred Requirements:

• Experience with enterprise AI adoption and agentic workflows

• Experience in e-commerce or marketplace technology

• Experience managing vendor partnerships and budgets

Compensation, Benefits, + Perks

• Employee Stock Purchase Plan

• 401K with Company Match

• Medical, Dental & Vision Insurance

• Paid Parental Leave

• 9 Paid Company Holidays

• Flexible Time Off (With Manager Approval)

• Find out more about our Benefits here.

The expected salary range for this role is $-$. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR’s total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

The RealReal is the world’s largest online marketplace for authenticated, resale luxury goods, with 40 million members. With a rigorous authentication process overseen by experts, The RealReal provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of in-house gemologists, horologists, and brand authenticators who inspect thousands of items each day. As a sustainable company, we give new life to pieces by thousands of brands across numerous categories—including women's and men's fashion, fine jewelry and watches, art, and home—in support of the circular economy. We make selling effortless with free virtual appointments, in-home pickup, drop-off, and direct shipping. We handle all of the work for consignors, including authenticating, using AI and machine learning to determine optimal pricing, photographing and listing their items, as well as shipping and customer service. 

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That’s why diversity and inclusion are vital to our priorities as an equal opportunity employer. You can read about our Diversity Equity and Inclusion program here.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.