Oliver Wine

Senior Corporate Real Estate Executive

basedChicago, IL
phone···
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Executive Summary

Corporate real estate executive with 12+ years leading national portfolio strategy, lease administration, and workplace transactions for one of the country's largest mortgage companies. Built the corporate real estate function at Guaranteed Rate from the ground up — growing it from a single coordinator role into a full-scale department managing 900+ locations across all 50 states. Known for disciplined transaction execution, data-driven portfolio optimization, and the ability to align real estate strategy with rapidly evolving business objectives.

12+ yrs
Leading the function
900+
Locations managed
50 states
National footprint
$50M+/yr
Real estate spend
02

Core Competencies & Credentials

Corporate Real Estate Strategy Lease Negotiation & Administration Portfolio Management Transaction Management Site Selection Workplace Strategy M&A Integration Joint Venture Standup KPI Development & Reporting Vendor Management Budget Management Team Leadership
License
Illinois Real Estate Managing Broker
Platforms
CoStar · Tango Analytics · Lease Harbor · Yardi
Tooling
MS Office Suite · Google Workspace
AI
AI Tools & AI-Assisted Workflows
Education
B.A. Economics — Lake Forest College, 2011
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Professional Experience

2020 — Present

Senior Vice President, Corporate Real Estate

Guaranteed Rate, Inc.

Lead corporate real estate strategy and operations for one of the nation's largest mortgage companies, overseeing a 900-location, 50-state portfolio spanning retail branches, fulfillment centers, and corporate offices. Direct lease administration, transaction management, site selection, and workplace strategy with a $50M+ annual real estate spend.

  • Execute hundreds of lease transactions annually — new sites, renewals, restructures, and terminations — with a consistent focus on cost reduction and strategic portfolio flexibility.
  • Drive continuous occupancy cost savings at both the individual deal and enterprise portfolio level, aligning real estate spend with evolving business and headcount strategies.
  • Led real estate workstreams for multiple M&A integrations, onboarding acquired portfolios and standardizing operations across newly combined entities.
  • Stood up real estate infrastructure for new joint venture launches from scratch — building team structure, vendor relationships, and portfolio frameworks enabling rapid go-to-market.
  • Founded and scaled the corporate real estate department, establishing team structure, KPIs, performance dashboards, and technology platforms to manage a high-volume national footprint.
  • Served on COVID-19 crisis management working group; swiftly recalibrated portfolio strategy in response to remote work shifts, preserving flexibility while reducing fixed occupancy costs.
2017 — 2020

Vice President, Real Estate

Guaranteed Rate, Inc.

Built and led the corporate real estate team during a period of rapid organizational growth, establishing the foundational infrastructure — people, processes, and technology — that enabled the function to scale nationally.

  • Recruited, hired, and trained the corporate real estate team from scratch, building operational capacity to support high-volume transaction activity across a growing national portfolio.
  • Procured and implemented a purpose-built lease tracking and administration platform, ensuring portfolio scalability and positioning the company for lease accounting compliance (ASC 842).
  • Supported multiple M&A acquisitions and nationwide joint venture formations, leading lease due diligence and providing key integration recommendations.
  • Developed KPIs and performance dashboards to assess portfolio efficiency and location productivity, driving data-informed decisions on renewals, terminations, and new site investments.
  • Established department policies, procedures, and transaction standards that supported rapid growth while maintaining consistency and quality across all 50 states.
2015 — 2017

Corporate Real Estate Specialist

Guaranteed Rate, Inc.

Managed nationwide real estate transactions supporting approximately 100 net new location openings annually, working directly with senior sales leadership to align real estate execution with aggressive growth targets.

  • Drove end-to-end transaction management for ~100 net new locations per year, coordinating site selection, lease negotiations, and execution to support rapid national expansion.
  • Partnered directly with senior sales and recruiting leadership to align real estate strategy with revenue growth objectives, delivering market-entry solutions at pace.
  • Transitioned lease database from Excel to a purpose-built contract tracking platform, improving reporting accuracy and laying the groundwork for scalable portfolio management.
  • Built portfolio performance reporting and KPI frameworks to track location-level productivity and drive data-based optimization decisions.
  • Hired and onboarded the department's first direct report, beginning to scale the team infrastructure needed to manage growing transaction volume.
2013 — 2015

Real Estate Coordinator

Guaranteed Rate, Inc.

Supported a rapidly growing national commercial real estate portfolio from the ground up, managing high-volume lease transactions and building the operational infrastructure that would underpin the company's expansion.

  • Managed end-to-end commercial lease transactions — coordinating directly with landlords and brokers on new sites, renewals, and amendments across a fast-growing national footprint.
  • Owned lease abstraction, key date tracking, and internal approval workflows, ensuring accuracy and compliance across an expanding multi-state portfolio.
  • Coordinated cross-functionally with Legal, Finance, Compliance, HR, and Sales to align real estate activity with business objectives and regulatory requirements.
  • Built the department's initial lease tracking system and developed KPI frameworks to monitor portfolio performance and surface optimization opportunities.
2012 — 2013

Community Association Manager

Wesley Realty Group

Managed residential community associations; oversaw vendor relationships, budgets, maintenance operations, and board governance for multi-property portfolios.