Head of Transaction Support and Administration

About Cedar

Cedar is creating the most significant innovation in home affordability since the 30-year mortgage. By reimagining the land lease as a consumer-first model, Cedar makes homeownership more accessible and sustainable for a wider range of buyers. We are actually solving home affordability at scale – this is one of the most pressing problems in our country today and we are fixing it. Our structure meaningfully reduces both the upfront cost of purchasing a home and monthly costs. We expand the path to ownership for people who have been locked out of traditional markets and help existing homeowners access their equity at cost well below existing solutions. Cedar is already making a substantial impact for homeowners and we have material backing from top investors. Join our fast-growing and high-preforming team as we fundamentally change how people buy homes and create a new institutional asset class.

About the Role

Cedar Innovations is seeking a highly autonomous, detail-oriented, and operationally strong Head of Transaction Support & Administration to lead and manage Cedar’s residential transaction workflows, administrative operations, and default-notice systems. This is a key role of Cedar’s transaction and administrative pipeline — ensuring legal and administrative coherence, smooth customer experience, and precise coordination with title companies, lenders, and other third-party vendors.

This position is requires flexibility, structured thinking, high accountability, and the ability to thrive in a fast-moving, fluid environment. You will assist in designing and refining SOPs, manage staff, oversee third-party document quality, and help integrate Cedar’s operational processes into internal technology systems, automations, and dashboards.

This role coordinates administrators and specialists to support customer-facing administrative workflows for transaction management, finance/collections, and asset management, ensuring the admin team is well-equipped and fully staffed for Cedar’s national growth.

What You’ll Do

Transaction Support, Coordination & Documentation Oversight

• Oversee and coordinate all administrative support for residential real-estate transactions, ensuring smooth, accurate, and timely workflow execution.

• Manage and review transaction files across multiple jurisdictions, ensuring all administrative steps, notices, and documentation are handled accurately.

• Proactively coordinate with title companies, lenders, escrow officers, and third-party service providers to maintain seamless transaction progress.

• Conduct administrative review of documents for execution accuracy and completeness prior to closing.

• Perform quality-assurance checks on all third-party prepared materials, including title packages, closing statements, HOA/AOAO certificates, lender documents, and other external deliverables.

• Ensure meticulous organization, documentation, and filing of all transaction-related communications and materials.

• Draft standardized transactional notices and correspondence; amend administrative terms in contracts as needed under guidance from the CLO.

• Support internal legal workflows without directing or practicing legal judgment.

Administrative Operations, SOP Development & Team Leadership

• Manage, train, and supervise administrative assistants, transaction coordinators, and support specialists as Cedar scales.

• Assess ongoing staffing needs, forecast administrative workload, and recommend appropriate staffing levels for local, remote, and offshore administrative teams.

• Lead recruitment, interviewing, hiring, and onboarding of administrative staff, including domestic and offshore personnel for administrative and transaction management purposes.

• Delegate tasks effectively to maintain continuous workflow and prevent bottlenecks.

• Coordinate staffing, workload distribution, and daily prioritization across transaction support, finance/collections support, and asset management support.

• Assist leadership in designing and implementing Standard Operating Procedures (SOPs) for transaction support, administrative operations, and document workflows.

• Establish and maintain quality assurance and consistency standards for all administrative outputs.

• Maintain audit-ready administrative systems for tracking notices, correspondence, transaction steps, and document retention.

• Oversee performance management for all administrative staff, including evaluations, coaching, training, and corrective action when needed.

Default Notices & Administrative Compliance Support

• Oversee administrative preparation, issuance, and internal tracking of default notices related to residential leaseholds and internal agreements.

• Coordinate with internal teams to ensure notices are accurate, timely, and properly documented.

• Maintain Cedar’s internal library of administrative notice procedures and ensure team adherence.

• Support the CLO and CCO operationally in evolving administrative and compliance needs.

Systems, Technology Integrations, Automation & Dashboards

• Collaborate with engineering, platform, and product teams to integrate administrative and transaction-support workflows into Cedar’s internal systems.

• Assist in deploying automation tools to streamline administrative processes such as document generation, notice sequences, workflow triggers, and data entry.

• Assist in developing and maintain operational dashboards tracking transaction progress, notice timelines, administrative workload, and bottlenecks.

• Provide structured operational feedback to inform system improvements, product features, and workflow automations.

• Test software enhancements, new system tools, and integrations to ensure operational readiness prior to deployment.

Cross-Functional Coordination & Process Optimization

• Work closely with the CLO on document workflows, contract administration, and process adherence.

• Partner with the CCO to scale administrative operations and align staffing plans with national growth.

• Coordinate with Underwriting, Transaction Management, and Platform teams to ensure smooth administrative handoffs and documentation flow.

• Identify administrative bottlenecks, inefficiencies, or workload imbalances; recommend staffing adjustments or workflow changes as needed.

• Develop and track KPIs for administrative throughput, accuracy, productivity, and process health.

Property Documentation Review & Administrative Risk Identification

• Interpret HOA, AOAO, and CC&R documents to identify administrative obligations, restrictions, and follow-up tasks.

• Review inspection reports, disclosures, and related materials to identify administrative issues, missing documentation, or required follow-ups.

• Support property readiness by ensuring administrative components of each transaction are complete, accurate, and aligned with underwriting and asset management processes.

What We Need

We are looking for a highly organized, autonomous operator who thrives without constant supervision and consistently drives work to completion. This person is a natural manager, capable of leading administrative assistants, transaction coordinators, and future team members while delegating effectively to ensure seamless day-to-day operations. They are comfortable managing multiple transactions simultaneously across jurisdictions and are equally at ease drafting notices, reviewing and annotating contracts, handling detailed documentation, or partnering with engineers and support teams to automate and improve workflows.

They are deeply process-oriented and motivated to create order and structure, enjoy building and scaling SOPs, and continuously improve systems as the company grows. They perform well in a dynamic startup environment where responsibilities evolve, are results-oriented and proactive in identifying and preventing issues, and remain calm and effective when problems do arise. Strong consumer-facing written and verbal communication skills are essential, as this role plays a direct part in building trusted customer relationships.

Qualifications

• Minimum 6 years of real estate experience, including:

  • 2+ years in AOAO or HOA management;

  • 2+ years in residential transaction or document management;

  • 1+ year with leasehold estates (may overlap with other experience).

• Bachelor’s degree required; real estate licensure strongly preferred.

• Demonstrated ability to hire, supervise, and evaluate administrative staff.

• Experience managing distributed teams, including remote or offshore personnel.

• Strong organizational discipline and high attention to detail.

• Proficiency reviewing, amending, and quality-checking transactional and administrative documents.

• Ability to interpret HOA, AOAO, and CC&R documents and identify administrative or operational risks.

• Experience analyzing inspection reports and disclosures.

• Experience creating SOPs and applying internal QA processes.

• Experience collaborating with technical teams on workflow tools, dashboards, or automation.

• Able to operate independently in a hybrid or remote environment while managing competing deadlines.

• 5+ years in consumer-facing and customer service roles

• Experience forecasting workload and planning staffing models for administrative or transaction-heavy operations.

• Experience supervising administrative teams supporting real estate, escrow, HOA/AOAO, or collections workflows.

• Exposure to workflow automation or tech-enabled operations.

• Experience working with title companies, escrow officers, and lenders.

• Comfort with dashboards, task management software, or CRM systems.

Why Choose Cedar?

• Take real ownership early — the work is not theoretical

• Grow through direct feedback, rigorous debate, and steep responsibility

• Be pushed to develop judgment, not just skills

• Build a track record that compounds — responsibility scales with performance

Cedar is built for people who want to operate at a very high level on work that matters. We run a true owner’s culture: high standards, direct feedback, fast iteration, and accountability to outcomes. You’ll have real responsibility early, you’ll be expected to think—not just execute—and you’ll be surrounded by teammates who push hard and care deeply about excellence.

This is not a company for people who need perfect clarity, gentle consensus, or predictable routines. The pace is fast, the problems are complex, and the bar is high. But the upside is rare: steep growth, meaningful autonomy, and the chance to do career-defining work with a team that treats the mission seriously and rewards success well.

If you want comfort, you won’t like it here. If you want to build, learn, and win—Cedar is the place.