Summary
Overview
Work History
Education
Skills
Certification
Languages
Timeline
Generic

Crysta Osborne

Chicago,IL

Summary

Dynamic and results-oriented executive operations leader with over 20 years of progressive experience in CEO and executive support, people operations, and organizational management. Expertise in serving as an Agency Principal proxy, transforming ambiguity into structured workflows that enhance leadership efficiency. Proven track record in cultivating high-performance organizational culture initiatives, optimizing internal communications, and driving operational efficiency, including a remarkable 50% increase in office productivity. Strong foundation in HR compliance, encompassing payroll and benefits administration, combined with extensive project coordination and stakeholder engagement experience to effectively scale company values and foster alignment within a fast-paced, growth-oriented environment.

Overview

15
15
years of professional experience
1
1
Certification

Work History

Manager of Executive Operations Leadership Support

The Scion Group LLC
10.2022 - Current
  • Functioned as a key strategic liaison and thought partner to C-suite and partner executives, overseeing daily operational functions and ensuring stakeholder alignment on strategic priorities.
  • Managed complex, ever-evolving calendars for executives, meticulously coordinating high-profile meetings and global initiatives (e.g., Board Meeting Coordination) to ensure seamless punctual attendance.
  • Prepared detailed executive briefings, presentations, and necessary materials for leadership, enhancing overall operational efficiency and decision-making speed.
  • Identified and resolved operational bottlenecks and dependencies, demonstrating strong initiative and analytical problem-solving skills.
  • Provided essential support for executive activities, handling sensitive information with high-level discretion and professionalism.
  • Directed strategic initiatives to enhance operational efficiency and drive team performance.
  • Implemented process improvements that reduced turnaround time and increased service quality.
  • Led strategic initiatives to enhance operational efficiency across multiple properties.
  • Led cross-functional teams to improve operational efficiency and enhance service delivery.
  • Developed and implemented strategic plans aligning departmental goals with organizational objectives.
  • Led cross-functional teams to enhance operational efficiency and streamline processes.

District Manager - Senior New Business Manager

MassMutual – Hoopis Financial Group
02.2016 - 10.2022
  • People Operations & HR Compliance: Oversaw the administration of the employee lifecycle for up to 240 employees, including collaboration on hiring, onboarding, and offboarding.
  • Payroll & Benefits Administration: Led sensitive financial oversight, managing confidential attendance reporting, payroll coordination, and conducting operational audits to ensure HR compliance with labor laws and regulations.
  • Culture & Engagement Champion: Introduced operational policies that resulted in a 50% increase in office efficiency and developed staff training initiatives to improve employee engagement, recognized with the Best Employee Award in 2018.
  • Implemented strategic initiatives to drive sales growth and improve client engagement.
  • Directed team operations to enhance productivity and service delivery across multiple districts.

Office Manager - Licensing & Contracting Specialist

MassMutual – Hoopis Financial Group
01.2011 - 01.2016
  • Internal Communications & Event Management: Organized team-building events and managed multi-department contracts, acting as an internal liaison to support company culture and Employee Engagement.
  • Business Administration & Compliance: Coordinated complex licensing and contracting processes, meeting strict compliance timelines and managing confidential documentation.
  • Financial Tracking: Managed day-to-day operations and supply inventory, including essential budget monitoring for facility readiness and professional office atmosphere.
  • Partner Engagement: Managed vendor relationships and contracts, ensuring service excellence for external partners.
  • Coordinated staff training programs to enhance team productivity and performance.
  • Streamlined office operations by implementing efficient scheduling and communication systems.
  • Maintained relationships with suppliers for 3 years
  • Oversaw contracts for over 8 different departments using both manual and automated strategies.

Education

Bachelor of Science -

Cornell University
NY

Skills

  • Executive Leadership & Strategy
  • People & Culture Operations
  • Financial & Compliance Management
  • Executive Support / Principal Proxy
  • Culture & Engagement Champion
  • HR Compliance & Labor Law
  • Organizational Planning & Strategy
  • Internal Communications
  • Payroll Coordination & Benefits Admin
  • Experience with ADP systems
  • Travel and expense reporting
  • Proficient in Slack
  • ClickUp
  • Process Optimization
  • Employee Lifecycle Administration
  • Budget Monitoring & Expense Reporting
  • Stakeholder Engagement
  • Event Management & Retreat Planning
  • Vendor Coordination & Contract Management
  • Project Coordination & Management
  • Onboarding & Training Development
  • Business Administration
  • Technical Proficiencies
  • Microsoft Office (Expert)
  • Google Workspace
  • Workday/Concur (HR/Expense Systems Familiarity)
  • Proficient in Slack
  • Experienced with Notion tools
  • Effective team leadership
  • Strategic decision-making
  • Client support
  • Time management
  • Team leadership
  • Customer service
  • Decision-making
  • Sprout eLearning

Certification

  • CEA, Certified Executive Assistant
  • Certified Administrative Professional (CAP), IAAP
  • CM (Certified Manager)
  • CPM, Certified Professional Manager

Languages

English

Timeline

Manager of Executive Operations Leadership Support

The Scion Group LLC
10.2022 - Current

District Manager - Senior New Business Manager

MassMutual – Hoopis Financial Group
02.2016 - 10.2022

Office Manager - Licensing & Contracting Specialist

MassMutual – Hoopis Financial Group
01.2011 - 01.2016

Bachelor of Science -

Cornell University

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Crysta Osborne