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
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 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.
Skills Required
- 10+ years of progressive technical operations leadership
- Experience running enterprise IT or infrastructure at scale in a multi-site environment
- Experience leading enterprise AI enablement initiatives and deploying enterprise AI platforms
- Hands-on knowledge of networking, endpoint/device management, MDM, and distributed infrastructure
- Experience managing enterprise applications such as NetSuite, Workday, Salesforce, Google Workspace, or Okta
- Experience managing enterprise application vendors and stakeholders
- Experience building and operating incident and problem management functions
- Experience with postmortems and continuous improvement processes
- Demonstrated ability to attract, develop, and empower high-performing teams
- Experience partnering with Security, Product and Technology, Finance, and Retail Operations leaders
- Ability to balance hands-on execution with strategic planning in a fast-paced environment
- Excellent communication skills and experience influencing executive stakeholders
- Bachelor's degree in Computer Science, Information Systems, or related field, or equivalent practical experience
- Ability to travel up to 10%
- Experience with enterprise AI adoption and agentic workflows
- Experience in e-commerce or marketplace technology
- Experience managing vendor partnerships and budgets
The RealReal Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about The RealReal and has not been reviewed or approved by The RealReal.
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Healthcare Strength — Health coverage includes multiple medical, dental, and vision options along with six free therapy sessions, and company HSA contributions for high‑deductible plans.
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Parental & Family Support — Family-building support includes inclusive fertility coverage with a high lifetime maximum and up to 10 weeks of paid parental leave plus additional disability pay for birthing parents.
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Equity Value & Accessibility — An Employee Stock Purchase Plan with a 15% discount is available to both full‑ and part‑time employees, expanding total compensation beyond base pay.
The RealReal Insights
What We Do
The RealReal is the world’s largest online marketplace for authenticated luxury retail. 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 150+ in-house gemologists, horologists and brand authenticators who inspect thousands of items each day.
Why Work With Us
We are looking for smart and talented people who are creative, enjoy working in a fast-paced environment, and want to be part of a team that is reinventing the digital marketplace as you know it!
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