PMO Strategic Director, AI Transformation Programs

Recognized as the No. 1 site trusted by real estate professionals, Realtor.com® has been at the forefront of online real estate for over 25 years, connecting buyers, sellers, and renters with trusted insights and expert guidance to find their perfect home. Through its robust suite of tools, Realtor.com® not only makes a significant impact on the real estate industry at large, but for consumers, navigating the biggest purchase they will make in their life, by providing a user experience that is easy to use, easy to understand, and most of all, easy to make decisions.

Join us on our mission to empower more people to find their way home by breaking barriers to entry, making the right connections, and building confidence through expert guidance.

At Realtor.com® , we are navigating a pivotal era of innovation. We are looking for a PMO Strategic Director to serve as a visionary leader for our AI Transformation Programs . In this high-visibility role, you will partner directly with Senior Leadership to define and execute the strategy for our Program Management Office, specifically driving cross-functional initiatives that center on AI organizational transformation and change management.

You won't just be managing projects; you will be shaping the future of how we work. This includes reimagining our organizational structure to maximize the benefits of automation, co-creating strategic hiring plans for elite talent like Machine Learning and Prompt Engineers, and developing sophisticated capacity models to quantify the impact of AI on our operations.

What You'll Do:

• Partner with Senior Leadership to develop and provide vision and strategy for the Program Management Office (PMO), specifically for cross functional initiatives, including the strategic AI Org Transformation and Change Management
• Drive timely execution of deliverables, focusing on program milestones and coordinating across teams/functions and internal stakeholders.
• Oversee Project Managers within the PMO and work with cross-functional stakeholders, tracking and reporting on all program day-to-day activities and overall program health.
• Direct strategic discussions on prioritizing initiatives considering impact and capabilities.
• Anticipate how every decision, will be viewed by each stakeholder to maximize success
• Establish program objectives and key results (OKRs) for the PMO, and translate these OKRs into priorities for each cross-functional team, with a clear focus on outcomes.
• Hold accountability to executive management and the individual organizations for program financial and strategic results
• Inspire and problem-solve with all cross-functional teams to overcome the internal and external challenges
• Identify future critical program challenges before they become problems; anticipate, escalate, and problem-solve these challenges with executive leadership

What Success Looks Like:

• Help shape the organizational structure and individual roles to maximize the benefits of AI and automation
• Support the development of a sophisticated capacity model that projects the quantitative reduction in person-hours required for automated tasks.
• Co-Create a strategic hiring plan to quickly onboard critical, scarce talent (e.g., Machine Learning Engineers, Prompt Engineers, AI Ethicists). Whilst Simultaneously, establish criteria for identifying and prioritizing existing high-potential employees for internal reskilling into these new roles.
• Execute on an organizational hierarchy that facilitates the integration of AI tools directly into business units. Focusing on establishing fluid, project-based teams centered on key business outcomes, fostering speed and responsiveness

How We Work:

We balance creativity and innovation on a foundation of in-person collaboration. For most roles, our employees work three or more days in our offices, where they have the opportunity to collaborate in-person, adding richness to our culture and knitting us closer together.

What You Bring:

• Bachelor’s degree with 12 - 15 years of experience, ideally in corporate strategy, management consulting, and/or a similar PMO leadership role in a leading technology company, with significant experience in AI/ML product development or program management; real estate experience a plus.
• Masters of Business Administration, PMP certification, or a relevant ML certification preferred.
• Demonstrate excellent stakeholder management, influencing, and storytelling/communication skills, both verbal and written – convey complex information, especially regarding concepts and outcomes, in a concise manner to facilitate decision-making with the Organization.
• Proven track record leading complex cross-functional projects and programs within a PMO structure, maintaining an efficient plan, tracking issues, and proactively communicating progress against project milestones; exhibit high attention to detail in project management.
• Lead and execute quickly and independently in a highly visible and fast-paced -facing environment, specifically for AI-driven initiatives.
• Build trust-based relationships with stakeholders; collaborate effectively across a wide range of teams and seniority in the organization
• Adopt a ‘hands-on’ attitude – dive into execution and operational matters, while maintaining focus on the longer-term strategic agenda of the PMO and Organization.
• Possess advanced MS Office or Google Suite skills; experience with AI/ML platforms and tools is a significant plus.

How We Reward You:

Realtor.com® is committed to investing in the health and wellbeing of our employees and their families. Our benefits programs include, but are not limited to:

• Inclusive and Competitive medical, Rx, dental, and vision coverage
• Family forming benefits
• 13 Paid Holidays
• Flexible Time Off
• 8 hours of paid Volunteer Time off
• Immediate eligibility into Company 401(k) plan with 3.5% company match
• Tuition Reimbursement program for degreed and non-degreed programs
• 1:1 personalized Financial Planning Sessions
• Student Debt Retirement Savings Match program
• Free snacks and refreshments in each office location

Do the best work of your life at Realtor.com®

Here, you’ll partner with a diverse team of experts as you use leading-edge tech to empower everyone to meet a crucial goal: finding their way home. And you’ll find your way home too. At Realtor.com®, you’ll bring your full self to work as you innovate with speed, serve our consumers, and champion your teammates. In return, we’ll provide you with a warm, welcoming, and inclusive culture; intellectual challenges; and the development opportunities you need to grow.

Diversity is important to us, therefore, Realtor.com® is an Equal Opportunity Employer regardless of age, color, national origin, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, marital status, status as a disabled veteran and/or veteran of the Vietnam Era or any other characteristic protected by federal, state or local law. In addition, Realtor.com® will provide reasonable accommodations for otherwise qualified disabled individuals.