Director of Brokerage (Managing Broker)

Director of Brokerage - Managing Broker
Cleveland, OH

Reports to: VP of Sales

About Cross Street

At Cross Street, we’re reimagining real estate from the ground up. We’re modern, human, and unapologetically ambitious. More than just leasing apartments or selling homes, we collaborate with developers to bring thoughtful buildings and memorable brands to life—places that feel as good as they look. We lead with hustle, heart, and real data, balancing creativity with strategy to drive results that matter. As we grow nationwide, we’re looking for entrepreneurial leaders who want to build something lasting: a community, a culture, and a company they believe in.

We’re hiring our first Director of Brokerage

If you're someone who thrives in a fast-moving environment, loves coaching agents, and has a deep passion for real estate and leadership, this is your moment. Your Mission

As Director of Brokerage (Managing Broker)

you’ll be responsible for launching, scaling, and overseeing all brokerage operations in Cleveland. You’ll recruit, develop, and inspire a team of talented brokers, ensure full compliance with state regulations, and play a critical role in the strategic growth of the company in this market. You’ll be the local face of Cross Street—both a coach and a captain.

In 1 Month, You Will...

• Get fully onboarded into Cross Street’s systems, tools, culture, and become fully integrated into the Cleveland team.
• Review and customize brokerage operations to meet Ohio regulatory standards.
• Continue networking locally to establish your presence in the Cleveland market.
• Collaborate with the leadership team to set market growth goals.
• Begin building a short list of potential broker recruits.

In 3 Months, You Will...

• Hire and onboard your first brokers and start building a powerhouse team.
• Lead team sales meetings and start offering coaching to support broker growth.
• Manage the quarterly financial reports for the Cleveland team.
• Establish local marketing and recruitment strategies in collaboration with the broader Cross Street team.
• Oversee your first full cycle of transactions as the Managing Broker at Cross Street.
• Begin tracking key performance metrics and adjusting strategies accordingly.

In 1 Year, You Will...

• Lead a high-performing Cleveland brokerage with a strong, collaborative culture.
• Consistently hit or exceed sales and growth targets.
• Be a go-to real estate leader in the Cleveland market.
• Play a major role in expanding our brand presence across the region.
• Have earned significant income through a combination of base salary, bonuses, and other incentives.

Key Responsibilities

• Sales Leadership & Strategy
• Drive local sales growth through strategy, leadership, and accountability.
• Motivate brokers to meet personal and team targets.
• Stay ahead of market trends and shift strategies when needed.
• Identify and pursue local business development opportunities.

Team Development & Culture

• Recruit, train, and retain top-tier real estate talent.
• Offer deal support, mentorship, and career development guidance.
• Build and maintain a culture of collaboration, energy, and performance.
• Lead engaging weekly meetings that educate and inspire.

Operations & Compliance

• Act as the official Managing Broker for Ohio operations.
• Ensure compliance with all state regulations and licensing requirements.
• Supervise the transaction process from contract to close.
• Maintain operational excellence and streamline brokerage processes.

Marketing & Client Engagement

• Collaborate on hyper-local marketing initiatives that build visibility and trust.
• Cultivate and manage client relationships to increase retention and referrals.
• Represent Cross Street at local events, panels, and networking opportunities.
• Manage the brokerage’s P&L, including budget planning and revenue forecasting.
• Track performance and provide regular reports to the leadership team.
• Identify cost-saving and revenue-boosting opportunities.

What We’re Looking For

• Active Ohio real estate license with Managing Broker designation (or ability to obtain).
• 8+ years of experience in real estate sales - team leadership or brokerage management experience preferred.
• Strong understanding of state laws and regulatory compliance.
• Passion for mentoring others and helping people grow.
• A people-first approach that fosters collaboration, not competition.
• Comfort working in a fast-growing, startup-style environment.
• Experience with budgeting, forecasting, and using data to drive decisions.

Why Join Cross Street?

• Competitive Compensation: Base salary + Commission + Generous Profit Sharing Structure (while the earning potential is unlimited, we estimate OTE to be $200k-$700k+)
• Generous Perks: Paid time off, Health Benefits, and more
• Entrepreneurial Autonomy: The opportunity to build and lead your own market.
• Modern Tools & Support: From marketing to tech, we’ve got your back.
• Collaborative Culture: We work hard and we laugh a lot doing it.
• Mission-Driven: We’re in this to build something better for agents and clients alike.

If you’re ready to grow something big, empower others, and make your mark in Cleveland’s real estate scene, we’d love to hear from you.