Chief Operating Officer

REAL New York is a leading New York City real estate brokerage specializing in landlord-forward rental and sales of residential and commercial properties. With a growing portfolio of clients, the firm has built a competitive advantage through deep market knowledge, strong landlord relationships, and a hands-on approach to leasing and development advisory.

As REAL New York enters its next phase of growth, the co-founders are making a deliberate investment in leadership, operational infrastructure, financial discipline, and technology; positioning the firm to scale intelligently in an increasingly competitive market.

The Opportunity

REAL NY is seeking a Chief Operating Officer to serve as the senior leader of the business. This is not a traditional ops role. The COO will own five interconnected pillars — finance, people, operations, technology, and strategy and will be the executive layer between the co-founders and the rest of the organization.

The ideal candidate is a seasoned NYC real estate professional who is equally comfortable presenting a financial model, leading a technology roadmap, and building a high-performing team. This person runs the business so the co-founders can focus on what they do best — building relationships with landlords, developers, and institutional clients.

Five Pillars of Ownership

• Corporate Strategy
• Finance
• People and HR
• Operations
• Technology

Key Responsibilities

Corporate Strategy

• Partner closely with the co-founders to shape long-term company direction, identify opportunities for growth and strategic alliances, and provide executive-level input on business initiatives, staffing, and operational priorities.

Finance & Accounting

• Lead all finance operations, ensuring a scalable and efficient team structure that supports company growth
• Collaborate closely with the established finance team and co-founders on P&L review, financial planning, and continuous process improvement
• Maintain rigorous financial controls and reporting accuracy across accounts payable/receivable, collections, month-end close, and reconciliation
• Oversee budget projections, monthly goal reporting, and financial analysis to support strategic decision-making
• Develop and model commission structures for new and existing projects, ensuring accuracy, competitiveness, and compliance
• Advocate for agent commission structures that balance retention with REAL NY's profitability goals
• Identify cost-saving opportunities, lead vendor negotiations, and manage ongoing vendor relationships
• Oversee regulatory compliance across all business entities, including licensing, LLC renewals, and commission structures
• Manage bookkeeping infrastructure including QuickBooks oversight, invoice processing, check preparation, and wire reconciliation

People & Human Resources

• Oversee all HR functions including recruitment, retention, benefits administration, and performance management
• Develop and maintain employee and agent HR policies, ensuring a consistent, professional, and positive work environment
• Create and manage onboarding processes, employee handbook, PTO policies, and workplace standards
• Develop and implement training programs and professional development initiatives in partnership with department directors
• Monitor agent performance and provide structured feedback and development pathways
• Manage recruitment strategy across all roles employees, agents, and leadership including outside recruiters and job platforms
• Build a culture of accountability, collaboration, and high performance

Operations & Administration

• Oversee day-to-day business operations, ensuring systems, processes, and workflows are efficient and scalable across all departments
• Manage and develop administrative staff and virtual assistants, providing clear direction, accountability, and growth opportunities
• Oversee office management functions including facilities, vendor relationships, and supply and service contracts
• Serve as the connective tissue between departments, technology initiatives, and co-founder priorities ensuring alignment, eliminating bottlenecks, and keeping the organization moving in the same direction
• Mentor and develop a team of directors, building capability and performance at the leadership level
• Oversee outside legal counsel for errors and omissions, fair housing, contract agreements, and personnel matters
• Manage legal budget and ensure fair housing compliance systems are in place and maintained
• Plan, budget, and oversee execution of company events and corporate announcements

Technology & AI Implementation

• Serve as the primary business owner of REAL NY's internal systems roadmap, translating founder vision and department needs into clear priorities, timelines, and success metrics
• Partner closely with the internal technology lead to define what should be built, bought, improved, paused, or retired — owning the business side of every technology decision
• Establish a recurring technology steering cadence with the co-founders and technology lead, maintaining a clear Now / Next / Later / Not Now roadmap
• Protect the technology team from reactive, ad hoc requests by creating a structured intake and prioritization process
• Drive adoption of existing systems and tools including Zoho, dashboards, reporting tools, and AI-enabled workflows diagnosing where adoption is lagging and creating plans to improve it
• Own internal documentation and knowledge management so critical process and systems knowledge is never dependent on a single person
• Translate technical constraints, tradeoffs, and timelines into clear business language for founders, department heads, and staff

Ideal Candidate Profile

• 8–15 years of progressive leadership experience in NYC real estate — brokerage, property management, or development strongly preferred
• Proven executive leadership experience managing cross-functional teams and business operations at a senior level
• Strong financial acumen — comfortable owning P&L, overseeing accounting functions, and presenting to executive stakeholders
• Demonstrated experience with AI tools, real estate technology platforms, and technology implementation strategy
• Track record of building and scaling HR, recruiting, and people operations functions
• Deep understanding of the NYC residential rental and new development market
• Highly organized operator who can hold strategy and execution simultaneously
• Exceptional communicator equally effective with co-founders, department directors, agents, and external partners
• Entrepreneurial mindset with the ability to thrive in a growing boutique environment
• Bachelor's degree in business, real estate, or related field required; MBA or JD a plus

Who You Are

• A builder and operator you don't just strategize, you execute
• Hungry and engaged you want to make a measurable impact, not manage the status quo
• A natural translator you make technology accessible, finance understandable, and strategy actionable
• A people developer you invest in the people around you and take mentorship seriously
• Comfortable with ambiguity you can hold multiple priorities and make sound decisions with incomplete information
• A steady presence you create calm, clarity, and momentum even when the business is moving fast

Why This Role

This is a rare opportunity to step into a senior leadership role within a respected NYC brokerage and have genuine influence over how the company operates, grows, and positions itself for the future. You will work directly alongside the co-founders, own the full business infrastructure, and build something that lasts.

Benefits:

• 401(k)
• Dental insurance
• Employee discount
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: In person