Summary
Overview
Work History
Education
Skills
Certification
Accomplishments
Timeline
Generic

Olive Holloway

Chicago

Summary

Dynamic professional with 20+ years of experience driving business growth, client satisfaction, and operational efficiency across leasing, sales, and administrative support. Proven ability to build strong relationships, negotiate agreements, and manage projects while leveraging CRM systems and market insights to achieve measurable results. Skilled in team leadership, client engagement, and process optimization, with a track record of delivering exceptional service in fast-paced, high-demand environments.

Overview

19
19
years of professional experience
1
1
Certification

Work History

Lesing Specialist

DAC Team/ Compass
Chicago
05.2025 - Current
  • Partner with the Compass real estate team to deliver luxury leasing solutions, specializing in high-demand Chicago neighborhoods.
  • Conduct tailored property tours and consultations, achieving consistently high lease conversion rates through personalized client engagement.
  • Manage a diverse client pipeline using CRM tools, ensuring accurate tracking of leads, follow-ups, and deal progress.
  • Collaborate with property owners and developers to implement pricing strategies based on market analysis, maximizing occupancy, and rental income.
  • Negotiate lease terms and agreements that align tenant needs with property standards, fostering long-term satisfaction and retention.
  • Coordinate with marketing teams to design targeted campaigns that attract qualified prospects, and strengthen brand presence.
  • Provide white-glove service to clients, cultivating relationships that generate referrals and repeat business.

Leasing Agent

North Water
Chicago
06.2024 - 07.2025
  • Achieved a 95% lease conversion rate through customized tours and client-focused service.
  • Negotiated leases aligning tenant needs with property policies, boosting satisfaction, and retention.
  • Implemented targeted marketing strategies to attract high-net-worth clients, increasing occupancy.
  • Analyzed market trends to adjust pricing strategies, sustaining high occupancy, and maximizing revenue.
  • Streamlined leasing operations and showings, enhancing efficiency and client experience.

Account Manager- Collections

Discover
Chicago
11.2022 - 05.2024
  • Negotiated payment plans and financial arrangements, recovering delinquent accounts while maintaining compliance.
  • Developed innovative recovery strategies for high-risk accounts, improving collection effectiveness.
  • Partnered with cross-functional teams to optimize communication and payment processes.
  • Ensured compliance with FDCPA guidelines while documenting account activity for regulatory audits.
  • Maintained accurate records of all customer interactions in the CRM system.

Guest Services

Kirkland & Ellis
Chicago
03.2020 - 09.2023
  • Directed guest services operations, consistently exceeding service quality and satisfaction benchmarks.
  • Implemented new SOPs and led a DMS migration project, improving efficiency and accuracy.
  • Coordinated staff schedules and training programs to optimize operational performance.
  • Collaborated with Security and Risk Management to ensure seamless front-of-house operations.
  • Coordinated room assignments, check-in and check-out processes and other guest services activities.

Leasing Receptionist

NEMA
Chicago
04.2019 - 03.2020
  • Supported leasing operations through database management and CRM data integrity checks.
  • Assisted property managers and executives with administrative and client-facing support.
  • Coordinated vendor relationships and supply management, reducing operational costs.
  • Facilitated client relations by managing schedules, events, and communication workflows.
  • Assisted in the preparation of regularly scheduled reports by collecting and analyzing information.

Assistant Selling Manager

Hugo Boss
Chicago
03.2012 - 08.2018
  • Spearheaded retail operations, generating $4.5M in annual sales while mentoring the sales team.
  • Implemented client acquisition strategies, strengthening customer loyalty, and repeat business.
  • Directed recruitment, onboarding, and training initiatives to elevate team performance.
  • Analyzed KPIs to provide senior management with actionable insights for business growth.
  • Assisted in daily store operations and maintained visual merchandising standards.

Executive Assistant

Icon Group Entertainment
Chicago
10.2006 - 10.2013
  • Coordinated executive schedules, travel, and event logistics across multiple departments.
  • Managed budgets, invoices, and expense reporting to ensure financial accuracy.
  • Built vendor and stakeholder partnerships to deliver successful, high-profile corporate events.
  • Streamlined workflows by developing administrative processes that improved organizational efficiency.
  • Managed confidential documents and maintained secure filing systems for sensitive information.

Education

DePaul University
Chicago, IL

Southwestern College
Chula Vista, CA

Skills

  • Notary public
  • Executive management support
  • scheduling and calendar management
  • PeopleSoft HRMS
  • IT and technical support
  • Confidential document management
  • CRM and database support
  • Expense reporting
  • Microsoft Office Suite, Google Suite
  • Process improvement
  • Data analysis and reporting
  • Financial management
  • Market research
  • Recruitment and talent acquisition
  • Customer relationship management
  • Sales and business development
  • Event planning and coordination
  • Real estate market knowledge

Certification

Project Planning, PGNCHU7L3V35
Project Initiation, QC6BCJH2UVJY
Foundations of Project Management, 3JZKG35TUZ72
Project Execution, 95NU2WVMH8MG
Agile Project Management, 92TX4ELY7NBJ
Capstone: Applying Project Management in the Real World, 39H5E6WU7FRQ

Accomplishments

  • Top 25 Sales Leader

Timeline

Lesing Specialist

DAC Team/ Compass
05.2025 - Current

Leasing Agent

North Water
06.2024 - 07.2025

Account Manager- Collections

Discover
11.2022 - 05.2024

Guest Services

Kirkland & Ellis
03.2020 - 09.2023

Leasing Receptionist

NEMA
04.2019 - 03.2020

Assistant Selling Manager

Hugo Boss
03.2012 - 08.2018

Executive Assistant

Icon Group Entertainment
10.2006 - 10.2013

DePaul University

Southwestern College

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