Skarllette O'Leary
Pasadena,MD
Summary
Results-driven business professional with over 20 years of proven success in leadership, accounting, training, financial management, and correctional and court operations. Demonstrated expertise in managing teams, optimizing business processes, and delivering performance that exceeds organizational goals. Skilled in balancing multiple priorities while driving operational efficiency and productivity improvements.
Extensive background in collections, lending, and strategic planning, complemented by hands-on experience within correctional environments and court systems. Proven ability to implement initiatives that enhance performance, ensure compliance, and support organizational objectives. Known for strong leadership, sound judgment, and a commitment to continuous improvement in high-accountability settings.
Overview
30
30
years of professional experience
1
1
Certification
Work History
Courtroom Clerk
Maryland Judiciary
Annapolis, MD
06.2025 - Current
- Managed courtroom schedules and maintained accurate records of proceedings.
- Assisted judges by preparing case files and ensuring timely access to necessary documents.
- Coordinated communication between court officials, legal representatives, and the public.
- Implemented improved filing systems to enhance document retrieval efficiency and accuracy.
- Oversaw case management processes, ensuring compliance with legal standards and timelines.
- Safeguarded sensitive information with meticulous record-keeping practices, ensuring the confidentiality of all court-related data.
Criminal/Traffic Clerk
Maryland Judiciary
Annapolis, MD
02.2025 - 06.2025
- Processed and distributed court documents to ensure timely delivery.
- Maintained accurate records of case filings and legal correspondence.
- Coordinated scheduling of court hearings and managed calendars for judges.
- Assisted in training new staff on filing procedures and office protocols.
- Leveraged strong communication skills for effective coordination with carriers, drivers, vendors, and customers.
Correctional Records Clerk
Anne Arundel County Detention Center
Annapolis, MD
04.2023 - 02.2025
- Organized and maintained accurate inmate records, ensuring compliance with legal standards.
- Processed incoming documents and requests, streamlining information retrieval for staff.
- Implemented filing procedures that enhanced efficiency of document management systems.
- Trained new personnel on record-keeping protocols and system navigation.
- Conducted audits of record accuracy, identifying discrepancies and implementing corrective actions.
- Collaborated with law enforcement agencies to ensure timely sharing of relevant inmate information.
- Maintained accuracy of records by verifying accuracy of data in records.
Senior Corporate Trainer/Performance Improvement Training Professional
Lendmark Financial
MD
04.2017 - 04.2023
- Virtual and Instructor led trainer.
- Create, edit, and implement new training courses and content.
- Instructional Design – brainstorming, planning process, creating, completing, presenting, training, and company rollout.
- Manage multi learner transcripts adding, deleting, and editing courses as needed by the learners.
- Managing curriculum – editing current curriculum due to policy changes, and adding new curriculum.
- Managing exams – editing current exams due to policy and law changes, and adding new exams and questions.
- Spearhead projects either alone or leading a team always meeting exceeding deadlines and goals.
- Create and maintain documentation for Procedures in new system companywide.
- Testing and any duties as assigned with new system conversion.
Field Trainer/Instructor/Instructional Design
Lendmark Financial
MD
04.2016 - 04.2023
- Virtual and Instructor led trainer.
- Deliver to large and small sessions, with same class engagement and time management.
- Instructional Design – brainstorming, planning process, creating, completing, presenting, training, and company rollout.
- Manage multi learner transcripts adding, deleting, and editing courses as needed by the learners.
- Managing curriculum – editing current curriculum due to policy changes, and adding new curriculum.
- Managing exams – editing current exams due to policy and law changes, and adding new exams and questions.
- Spearhead projects either alone or leading a team always meeting exceeding deadlines and goals.
Branch Manager
Lendmark Financial
Glen Burnie, MD
01.2014 - 04.2016
- Transferred to this location to reduce the company’s percentage of delinquent accounts. Within two weeks, reduced delinquent accounts from 17% to 10%.
- Reduced personal loan processing time from 4.85 days to same day, and increased personal loans by 80 percent.
- Exceeded all credit insurance sales expectations, making this location one of the top insurance sellers.
- Improved employee morale by identifying and utilizing strengths of each employee.
- Accepted full responsibility to approve time, verify accuracy, and process payroll.
CSR / Branch Manager
Lendmark Financial
Randallstown, MD
10.2003 - 01.2014
- Managed staff of four consumer loan specialists with a portfolio of $7M.
- Managed a branch that ranked in the top ten consistently for three years.
- Provided oversight of branch budgeting, business plan development, capital expenditures, cash management, collections, expense accounts, financial analysis, financial reporting, inventory costs, and inventory purchases.
- Provided exceptional customer service resolving complaints, thereby eliminating any need for escalation.
Front End Supervisor
Factory Card Outlet
Annapolis, MD
07.2003 - 10.2003
- Organized and ordered supplies and stock to ensure consistent stock availability.
- Improved employee morale by maintaining adequate staffing, which also resulted in higher customer satisfaction.
- Exceptional attention to detail, cost control, organization and store cleanliness resulted in promotion from backroom Coordinator to front end supervisor.
Store Manager
McDonald’s
Essex, MD
12.1995 - 06.2003
- Began as crew member, promoted to shift manager, next to assistant manager, finally to store manager.
- Designed marketing and sales campaigns.
- Maintained sufficient inventory levels.
- Managed product lines and vendors.
- Supervised assistant managers, business service teams, and management staff.
- Turned around a non-profitable store in under six months by improving customer service, reducing customer complaints by 80% and reducing labor costs.
Education
B.S. - Business Administration, Criminal Justice
University of MD
MD04-2028
B.S. - Business Administration, Criminal Justice
Liberty University
VA01-2017
Anne Arundel Community College
MARYLAND01-2012
High School Diploma -
Glen Burnie Senior Highschool
Glen Burnie05-1997
Skills
- Financial Management
- Goal Oriented
- Sound Leadership
- Training
- Office Management
- Excellent Multi-tasker
- Instructional Design
- Streamline Processes
- Results Driven
- Accounting
- Meeting Deadlines
- Strong Interpersonal Skills
- Advanced skills in Microsoft Office Products With working knowledge in Adobe, Goldpoint operating systems, Lexis Nexis products, ADP and Paycom payroll systems, Compliance 360 complaint tracking system, Intranet Help desk system, Cornerstone on Demand LMS Admin & authoring, Articulate Storyline, Sharepoint admin & user
- Training delivery
- Needs assessment
- Customer service training
- Course design
- Marketing
- Teamwork
- Problem-solving
- Time management
- Multitasking
- Attention to detail
- Organizational skills
- Adaptability and flexibility
Accomplishments
Recognized throughout career with multiple Branch of the Month, Quarter, and Year awards, as well as Portfolio Manager of the Year honors and additional recognition awards for outstanding performance. Committed to continuous professional development through industry seminars and training, bringing forward-thinking strategies and best practices to every role.
Certification
- Notary, for Baltimore County. Life and Health insurance Licensed.
- Certificate – Writing for Instructional Design - ATD 2017-12
Timeline
Courtroom Clerk
Maryland Judiciary
06.2025 - Current
Criminal/Traffic Clerk
Maryland Judiciary
02.2025 - 06.2025
Correctional Records Clerk
Anne Arundel County Detention Center
04.2023 - 02.2025
Senior Corporate Trainer/Performance Improvement Training Professional
Lendmark Financial
04.2017 - 04.2023
Field Trainer/Instructor/Instructional Design
Lendmark Financial
04.2016 - 04.2023
Branch Manager
Lendmark Financial
01.2014 - 04.2016
CSR / Branch Manager
Lendmark Financial
10.2003 - 01.2014
Front End Supervisor
Factory Card Outlet
07.2003 - 10.2003
Store Manager
McDonald’s
12.1995 - 06.2003
B.S. - Business Administration, Criminal Justice
University of MD
B.S. - Business Administration, Criminal Justice
Liberty University
Anne Arundel Community College
High School Diploma -
Glen Burnie Senior Highschool
RECOGNITION & ACTIVITIES
Special Recognition Award – Lendmark Financial for role in the US Bancorp acquisition., Branch Employee of the Quarter 2004 – Lendmark Financial., Zig Ziglar seminar (2001)., Portfolio Manager of the Year – Lendmark Financial (2008)., Lendmark Financial – Branch of the Month (2009 and 2010)., Special Recognition Award and Retail Lender of the Year Award – Lendmark Financial (2011 & 2019).