Strategic Initiatives Jobs in Reston, VA (NOW HIRING)

The real world is the next frontier, and at Metropolis, we are creating the artificial intelligence to make it responsive. We are pioneering the Recognition Economy — a future where mundane repetition disappears and being known unlocks access, comfort, and belonging everywhere you go. From transforming parking into a seamless drive-in, drive-out experience for millions of Members to expanding our intelligence layer across retail and hospitality, we are building a world that feels instinctive and magical. The future isn't coming; it's here, and we need builders, innovators, and problem solvers to help us create it.

Metropolis is seeking a VP, Strategic Initiatives to serve as the Chief Commercial Officer's primary operator for high-stakes, cross-functional projects that require senior judgment and decisive action. You are a parking industry veteran and high-accountability leader who thrives at the intersection of commercial ambition and operational execution. You take full ownership of complex initiatives like large-scale portfolio onboardings and enterprise-level system implementations without requiring constant oversight, leveraging your deep domain expertise to bypass the industry learning curve. As a peer to our Central Operations team, you will drive outcomes for our most critical projects. You are an expert at navigating ambiguity within the parking and real estate landscape, leading diverse stakeholders across Finance, Product, and Operations, and utilizing AI-driven approaches to multiply your impact and compress project timelines.

• Own end-to-end project management for CCO-level strategic initiatives from scoping through performance review
• Serve as the accountable, on-site leader for complex parking builds, big installs, and launches where a senior Metropolis presence is required
• Lead cross-functional alignment across Finance, Product, Operations, and Commercial stakeholders to secure multi-department buy-in
• Develop project charters, milestone frameworks, and accountability structures calibrated to project complexity
• Partner with Central Operations to oversee major property onboardings and serve as the expert escalation point for strategic parking and asset management decisions
• Manage the project infrastructure for large-scale portfolio onboardings to ensure readiness standards are met
• Drive the customer reporting improvement initiative across departments to deliver high-quality client-facing outputs
• Serve as the CCO's proxy on workstreams requiring senior presence and executive sponsorship
• Maintain the Operations OKR framework and data guide to ensure alignment with field-level performance
• Identify emerging strategic needs and proactively scope new initiatives before they become urgent

• 12+ years of progressive experience in operations, strategy, or project management inside the parking industry
• Extensive experience with big installs, asset management, and field-level leadership
• Demonstrated track record of owning complex, cross-functional projects from initiation through delivery within the parking or mobility sector
• Ability to communicate effectively with cross-functional stakeholders such as Finance, Product, and Commercial leaders to drive decisions
• High accountability orientation with a focus on owning outcomes rather than tasks
• Bachelor's degree required
• Operate as an AI-native leader by using AI tools to synthesize information, draft communications, and summarize data
• Experience implementing AI-driven approaches to automate reporting workflows and surface risks before they escalate
• Ability to proactively pilot and validate new AI tools to improve project outcomes and team efficiency
• Proven use of AI tools as a force multiplier for project status synthesis and cross-functional briefing preparation

• Specific experience in real estate or transportation technology industries
• Military or other high-accountability leadership backgrounds

4 Days in Office: Metropolis values in-person collaboration to drive innovation, strengthen culture, and enhance the Member experience. Our corporate team members hold to our office-first model, which requires employees to be on-site at least four days a week, fostering organic interactions that spark creativity and connection

When you join Metropolis, you'll join a team of world-class product leaders and engineers, building an ecosystem of technologies at the intersection of parking, mobility, and real estate. Our goal is to build an inclusive culture where everyone has a voice and the best idea wins. You will play a key role in building and maintaining this culture as our organization grows. The anticipated base salary for this position is $225,000.00 USD to $260,000.00 USD annually. The actual base salary offered is determined by a number of variables, including, as appropriate, the applicant's qualifications for the position, years of relevant experience, distinctive skills, level of education attained, certifications or other professional licenses held, and the location of residence and/or place of employment. Base salary is one component of Metropolis' total compensation package, which may also include access to or eligibility for healthcare benefits, a 401(k) plan, short-term and long-term disability coverage, basic life insurance, a lucrative stock option plan, bonus plans, and more. #LI-CH1 #LI-Onsite