Commercial Leasing Specialist

About the Role

This is a great opportunity for a commercial leasing professional who is ready to step into a role where their expertise truly shapes the business.

As our Commercial Leasing Specialist, you won't just be part of the process — you'll define it. You'll be the person who sets the standard, elevates the team, and brings clarity and confidence to every lease, every negotiation, and every conversation with ownership.

You'll champion deals from LOI to execution, guide Portfolio Managers through complexity with conviction, and bring your voice directly to ownership calls — because your insights will matter at that level.

If you have deep experience in commercial lease administration, a strong command of lease language, and a natural instinct for leading teams and driving decisions — this role was built for someone like you.

You’ll Thrive Here If You...

• Push back confidently when a deal term isn't right, a document is off, or a PM is about to make a costly mistake — and do it with clarity, not friction
• Are comfortable holding the line in a negotiation even when it's uncomfortable, because you understand what's at stake
• Feel a real sense of satisfaction when a complex lease comes together cleanly — the messier the situation going in, the more rewarding the resolution
• Read a lease the way other people read a contract — instinctively flagging what's missing, what's risky, and what needs to be renegotiated
• Thrive in calls with ownership because you come prepared, speak plainly, and know your stuff cold
• Take pride in being the person your team turns to — and make sure they always leave the conversation more informed than when they came to you

Our Service

In an ideal world, tenants would pay their rent on time, buildings would never have any issues, and the building owners could ride off into the sunset. The world isn't ideal. Rents are late. Things break. Help is needed. That is where we step in. Windsor provides a white-glove service so owners can still ride off into the sunset.

About Windsor

At our core, we are our people. We want talented teammates with whom we can work and win together. We strike a balance on speed and accuracy, owning our work through responsibility and delegation versus collaboratively relying on each other as a high-trust team, and solidifying procedures and establishing new ones. We know employees may leave our company over time, but we want to create an environment so amazing that it never crosses your mind. But if you do leave, we want you to know the value of the skills and development gained at Windsor so you can continue to thrive. With the best people both doing our own work and chipping in to make Windsor and each other better, Windsor can continue to thrive and grow, which creates more opportunities for everyone to develop.

Windsor Growth

Our reputation drives our growth. Our growth has been driven by 100% word-of-mouth referrals from happy clients and vendors. It is a testament to our collective, quality output and a testament to the staff we hire. Windsor was recognized in the Top 100 Fastest Growing Companies in the Bay Area in 2025, 2024, 2023 and 2022.

Responsibilities

Leasing Operations Ownership

• Own the end-to-end commercial leasing process, from LOI through execution, ensuring all leases are accurately abstracted and entered into Yardi in compliance with company standards.
• Serve as the internal expert on lease interpretation, providing clear guidance to Portfolio Managers on complex lease terms, clauses, and obligations.

LOI Review & Negotiation

• Review Letters of Intent received from brokers; redline and negotiate terms to protect company and ownership interests before lease drafting begins.

Document Management & Execution

• Oversee the drafting, preparation, and execution of lease documents, amendments, assignments, and tenant notices.
• Manage the full DocuSign signing workflow, proactively following up with all stakeholders to ensure timely execution.

Billing & Financial Accuracy

• Coordinate with the Windsor bookkeeper to ensure document fees are billed back to properties correctly and on time.
• Maintain financial accuracy across all lease-related billing activity.

Tracking & Reporting

• Build and maintain a comprehensive lease tracking system covering document status, key dates, completion milestones, and billing records.
• Provide regular reporting to leadership on portfolio-wide lease activity.

Team Leadership & Development

• Lead, mentor, and support team members on leasing best practices, compliance standards, and day-to-day leasing inquiries.