Summary
Overview
Work History
Skills
Education And Credentials
Timeline
Generic

CRYSTA OSBORNE

Chicago,Illinois

Summary

Results-driven Executive Office Manager with 10+ years of experience in providing comprehensive support to C-suite leaders. Proficient in managing complex calendars, arranging travel logistics, and acting as a liaison among various departments. Known for outstanding organizational and communication skills, maintaining confidentiality, and thriving under pressure. Expertise in operational oversight, HR coordination, and implementing efficiency improvements, with strong technical skills in enterprise applications.

Overview

23
23
years of professional experience

Work History

Office Manager – Executive Leadership Support 5x

The Scion Group LLC
Chicago, IL
10.2022 - Current
  • Manage diverse responsibilities encompassing daily operational activities and engagements with senior C-suite and partner firm executives
  • Managed daily schedules for multiple individuals, anticipating required materials and directions for activities.
    Maintained busy calendars and scheduled meetings, ensuring timely arrival of managers.
    Coordinated necessary background items for each scheduled activity to enhance efficiency.
  • Welcomed visitors and clients, creating a welcoming environment.
    Handled incoming calls to provide assistance and information.
    Scheduled conference rooms and coordinated meal logistics for events.
  • Oversee planning and execution of internal team huddle meetings, integrating venue sourcing, dining reservations, meal preparations, and creation of meeting documentation.
  • Manage extensive travel planning encompassing airline reservations, hotel accommodations, car rental bookings, car service arrangements, and driving directions as needed.
  • Oversee inventory management of supply stock for team
  • Manage and monitor expense reports and reimbursements with support from outside vendor.
  • Collaborate with teams to deliver backup support during assistants' paid time off and breaks.
  • Exhibited exceptional time management skills, detail orientation, and adaptability; managed multiple concurrent assignments while meeting deadlines with high accuracy in high-pressure environments.
  • Handle sensitive and confidential information while ensuring confidentiality
  • Exhibited outstanding phone etiquette alongside proficient management skills.
  • Utilized Microsoft Suite, including Word, Excel, Outlook, and PowerPoint.
  • Managed automated expense tracking and online travel tools efficiently.
  • Exhibited strong problem-solving and organizational capabilities.
  • Readiness to take initiative, accept responsibility, and deliver results; self-motivated with ability to work independently and with minimal supervision

District Manager | Senior New Business Manager

MassMutual - Hoopis Financial Group
Chicago, Illinois
02.2016 - 10.2022
  • Proceed with new business applications by collaborating with brokers and agents.
  • Evaluate each application's client profile, property record, and credit strength to make profit-oriented decisions.
  • Analyze and endorse documents to ensure compliance with guidelines.
  • Improve effectiveness through clear and open communication with agents and carriers.
  • Manage and edit knowledge base of multiple life insurance products and carriers.
  • Enlist application details into the database to effectively track progress.
  • Prepare reports and letters with notable clarity for insurance carriers and agents.
  • Increased office efficiency by 50% through continuous exceptional support and process enhancement.
  • Earned Best Employee Award in 2018 upon solid ethics and 5-star customer feedback.
  • Facilitated HR Manager in key functions of human resources, covering resume management and business document preparation.
  • Boosted business opportunities by fostering lucrative relationships.
  • Pioneered new employee manual, including professional development initiatives and disciplinary procedures and PTO, STD, FMLA, and FSA policies.

Licensing and Contracting Specialist

MassMutual - Hoopis Financial Group
Chicago, Illinois
01.2011 - 01.2016
  • Coordinated with insurance carriers, brokers, and agents to promptly address inquiries and responses.
  • Utilized insurance databases to generate regulatory reports.
  • Analyzed compliance programs to identify process improvement opportunities.
  • Successfully met licensing and contracting requirements.
  • Finalized all licensing certifications of new agents and carriers within time.
  • Boosted performance of employees by coaching on license requirements and compliance guidelines.
  • Nurtured reliable relations between personnel and management by effectively implementing team engagement activities.

Executive Assistant

MassMutual - Hoopis Financial Group
Chicago, Illinois
01.2007 - 01.2011
  • Oversaw correspondence, such as emails and letters.
  • Accomplished customer requests and service forms.
  • Developed crystal-clear policies and secured Policy Delivery Acknowledgement from customers.
  • Led all aspects of procurement and procured general supplies, business cards, and promotional materials at competitive prices.
  • Facilitated CEO, COO, VP, and other senior executives.
  • Constantly attained business goals by supporting new representatives.
  • Established cubicles for new representatives.
  • Accelerated productivity by tracking, monitoring, and revamping processes.

Front Office Receptionist

MassMutual - Hoopis Financial Group
Chicago, Illinois
01.2004 - 01.2007
  • Liaised and assisted residents, visitors, and vendors as the first point of contact, managed check-in and out process.
  • Oversaw surveillance cameras, life safety systems, and alarms to ensure zero suspicious activities.
  • Coordinated with manager to openly communicate injuries and accidents.
  • Nurtured reliable relationships with customers and staff members.
  • Delivered necessary support to carry out special project activities and achieve milestones.
  • Joined high-impact meetings to discuss safety conditions and improvement areas.
  • Secured and enhanced each resident satisfaction by swiftly addressing inquiries and resolving disputes.
  • Cultivated a healthy and safe environment by implementing security and safety policies.
  • Increased expertise and performance by actively attending training sessions.
  • Ensured exemplary customer service experience by quickly resolving issues and clearly communicating benefits.
  • Successfully oversaw 70+ general telephone and email inquiries on a daily basis.
  • Demonstrated organizational skills by cross-training and providing backup for other team members.

Finance Liaison

Euphoric Inc.
Remote
05.2002 - 12.2003
  • Coordinated interdepartmental communication to ensure project alignment.
  • Facilitated meetings to collect insights and feedback from stakeholders.
  • Maintained documentation for project workflows and processes efficiently.
  • Collaborated with teams to streamline operations and improve service delivery.
  • Demonstrated strong telephone etiquette while managing challenging calls.

Administrative Assistant

I-Many Inc.
Chicago, Illinois
  • Managed scheduling and calendar for executive team meetings and appointments.
  • Coordinated communication between departments to ensure timely project updates.
  • Organized office supplies and maintained inventory levels for operational efficiency.
  • Answered phone calls and emails to provide information, resulting in effective business correspondence.
  • Handled incoming calls and directed inquiries to appropriate personnel efficiently.
  • Prepared expense reports and processed invoices for timely payment approvals.
  • Handled confidential documents in an organized fashion according to established protocol.

Recruiter

Banner Personnel Service
Chicago, Illinois

Skills

  • Office management and oversight, vendor negotiation, inventory control, operational efficiency
  • Complex calendar management, travel logistics planning, support for C-suite executives
  • Managed and reconciled executive expense reports using Concur, consistently meeting compliance and reimbursement deadlines
  • Administered payroll and timekeeping functions via ADP, ensuring 100% accuracy across biweekly and monthly cycles
  • Supervised and mentored administrative teams (2–10 staff), improving workflow efficiency and boosting team engagement
  • Developed and rolled out internal policies and onboarding programs, reducing ramp-up time for new hires by 30%
  • Orchestrated corporate events, team offsites, and executive retreats, enhancing company culture and team cohesion
  • Streamlined supply ordering and procurement workflows, improving budget tracking, and vendor accountability
  • Supported employee performance evaluation cycles, optimizing timelines and coordination for quarterly and annual reviews
  • Managed contract documentation and database systems, improving accessibility and recordkeeping accuracy
  • Resolved internal conflicts and reconciliations, contributing to a more collaborative and solution-oriented team dynamic
  • Strengthened customer and client relationships through polished communication and proactive problem-solving
  • Handled high-level, confidential information with discretion, supporting legal and strategic communications
  • Created detailed executive briefing materials, meeting agendas, and action item tracking for leadership alignment
  • Led employee engagement initiatives, including recognition programs, social events, and culture-building campaigns
  • Leveraged advanced Microsoft Office skills to create dynamic reports, presentations, and executive dashboards
  • Implemented new office technologies and tools, accelerating administrative productivity and system adoption

Education And Credentials

  • Certified Administrative Professional (CAP) International Association of Administrative Professionals (IAAP)
  • Microsoft Office Specialist (MOS) Excel, Outlook, Word, PowerPoint — Microsoft Certified
  • Certificate in Office Management Coursera Completed coursework in operations, leadership, and workflow management
  • Concur Travel & Expense System – Certified User Trained in travel booking, expense reporting, and policy compliance
  • Managing Difficult Conversations Training Coursera – Conflict resolution and leadership communication
  • ATS Onboarding and Recruiting Training Emtrain – Applicant tracking systems and hiring best practices
  • Background Screening & Employment Compliance Coursera – Legal and operational considerations for hiring
  • Form I-9 Employment Eligibility Verification Training LIMRA – U.S. compliance with workforce documentation
  • Microsoft Applications Training Excel, PowerPoint, Access – Core and advanced feature instruction

Timeline

Office Manager – Executive Leadership Support 5x

The Scion Group LLC
10.2022 - Current

District Manager | Senior New Business Manager

MassMutual - Hoopis Financial Group
02.2016 - 10.2022

Licensing and Contracting Specialist

MassMutual - Hoopis Financial Group
01.2011 - 01.2016

Executive Assistant

MassMutual - Hoopis Financial Group
01.2007 - 01.2011

Front Office Receptionist

MassMutual - Hoopis Financial Group
01.2004 - 01.2007

Finance Liaison

Euphoric Inc.
05.2002 - 12.2003

Administrative Assistant

I-Many Inc.

Recruiter

Banner Personnel Service

Similar Profiles

CREATE PROFILE
CRYSTA OSBORNE