Legal Operations · Executive Support · Workflow & Governance

Bringing Structure to Complex, High-Accountability Work.

I improve workflows, manage complex legal and administrative processes, support leadership initiatives, strengthen operational controls, and keep critical work moving.

Across law firms, Army operations, and board governance, I have coordinated deadline-driven work, rebuilt process visibility, standardized recurring workflows, and supported decision-makers in environments where accuracy and follow-through matter.

Washington, DC Open to DC-Area, Hybrid & Remote Opportunities
Portrait of Glynn W. Hollingshead, Jr.
Legal operations Executive support Process improvement
90–100 Overdue Binders & Transcripts Resolved Restored control to delayed post-closing work.
$150K+ Annual Cost Exposure Addressed Policy and process recommendations with material business impact.
≤5 min. Standard Fannie Mae Loan Document Production Reduced a 90+ minute production workflow to minutes.
1,500+ Personnel Supported Through Army Operations Readiness, reporting, training, and accountability at scale.

Professional Profile

Operations Judgment Built in Demanding Environments

The common thread across my career is operational discipline: understand what must happen, create visibility around it, remove friction, and make execution more reliable.

My work sits at the intersection of legal operations, executive support, process improvement, and controlled execution. In legal practice, that has included high-volume multifamily real estate finance, litigation support, veterans’ claims, transaction coordination, closing and post-closing administration, deadline management, and execution-ready document production.

That experience is reinforced by active-duty Army operations leadership and current board governance responsibility. I am strongest in environments where multiple stakeholders, sensitive information, deadlines, documentation, and accountability all have to move together without losing control of the details.

Signature of Glynn W. Hollingshead, Jr.

Where I Add Value

Capabilities Built Around Control, Clarity, and Execution

Not a generic skills list—these are the operating functions that recur across my legal, military, governance, and administrative experience.

01

Legal & Transaction Operations

High-volume legal support, contract and transaction administration, closing/post-closing workflows, Fannie Mae/Freddie Mac delivery support, records organization, and attorney-directed work product.

02

Executive & Leadership Support

Calendar and priority coordination, confidential communications, leadership-facing materials, deadline visibility, and sustained support for leadership initiatives.

03

Workflow & Process Improvement

Workflow design, backlog remediation, standardized handoffs, reusable templates, document automation, process documentation, and practical operating controls.

04

Document & Information Control

Execution-ready document production, legal-file organization, electronic records, trackers, PDF production, document lifecycle management, and controlled handoffs.

05

Governance & Administrative Leadership

Board priorities, stakeholder communications, governance records, financial oversight, compliance administration, budgeting, vendor matters, and decision support.

06

Operational Readiness & Accountability

Reporting coordination, resource visibility, training accountability, structured communications, mission-response planning, and execution in high-accountability environments.

Selected Operational Impact

Operational Improvements with Measurable Results

Representative examples show the pattern behind the résumé: identify friction, improve the system, and leave the work more controlled than I found it.

Standardization

Scaling Workflow Improvements Across the Team

Developed standardized filing and administrative workflows, reusable pre-filled and auto-fillable forms, and improved handoff practices that moved process improvement beyond individual productivity.

Trained and retrained colleagues on document-production methods and workflow standards so improvements could be used consistently across the administrative team.

Cost & Process Review

$150K+ in Annual Exposure Addressed

Identified operating issues and recommended policy and process changes addressing more than $150,000 in annual fee exposure and excessive shipping costs.

The value was operational as well as financial: recurring administrative practices were examined as systems rather than accepted as fixed overhead.

Backlog Recovery

Restoring Control to Post-Closing Work

Resolved approximately 90–100 overdue binders and transcripts while introducing structured templates, completion tracking, and clearer workflow handoffs.

The result was both immediate backlog reduction and a more repeatable process for future post-closing execution.

Glynn Hollingshead in U.S. Army service uniform

U.S. Army · Active Duty

Operational Accountability at Scale

Managed operational readiness, reporting coordination, and training accountability for more than 1,500 paratroopers across multiple mandatory program areas.

Built reporting systems and operational resources that improved communication, deployment readiness, accountability, and leadership visibility.

Professional Experience

Experience Across Legal, Operational, and Client-Facing Environments

The website provides context; the downloadable résumé remains the complete application document.

Apr 2025 – Mar 2026Washington, DC

Legal Practice Assistant

Miles & Stockbridge P.C. · Legacy Krooth & Altman practice group

Supported four attorneys and two Senior Paralegal Specialists across high-volume multifamily finance matters during merger integration, coordinating document production, closing/post-closing deliverables, transaction records, custody-team processes, and backlog recovery.

Sep 2024 – Jan 2025Remote Contract · Washington, DC

Legal Administrative Assistant

Krooth & Altman LLP

Re-engaged remotely during a high-volume period to support closing production, transaction coordination, attorney scheduling, survey/title materials, closing records, and backlog reduction.

Apr – Nov 2024Orlando, FL

Front Desk Agent & Night Auditor

Homewood Suites by Hilton Orlando Airport

Managed overnight front-office and financial-audit responsibilities while protecting confidential information, cross-training employees, and introducing practical efficiency improvements.

Jan – Mar 2024Washington, DC

Litigation Legal Assistant / Paralegal

Morgan & Morgan DC PLLC

Supported a senior attorney with 130+ active matters across Washington, DC, Maryland, and Virginia, coordinating calendars, deadlines, discovery, depositions, hearings, mediations, trials, client communications, research, evidence, and filing workflows.

Oct 2023 – Jan 2024Washington, DC

Executive Support Associate (Paralegal)

Lieberman & Mark, PLLC

Supported veterans’ claims through legal research, VA and medical/service-record review, C-File analysis, case development, attorney-facing summaries, matter tracking, and process-optimization work.

Apr 2022 – Sep 2023Washington, DC

Administrative Legal Assistant

Krooth & Altman LLP

Supported five attorneys and three paralegals in a high-volume multifamily real estate finance practice, coordinating closings, post-closing documentation, Fannie Mae/Freddie Mac deliveries, records, transcripts, and workflow improvements adopted across the administrative team.

Oct 2018 – Feb 2022Active Duty · Various Locations

Operations Sergeant & CBRN Specialist

United States Army · Honorable Discharge

Managed operational readiness, reporting coordination, training accountability, communication systems, and mission-response resources in highly controlled, high-accountability environments.

Earlier Career

Lead Data Manager, Tetra Tech · Front Office Manager, Hampton Inn & Suites by Hilton · Attractions & Operations Attendant, Universal Studios Orlando

Leadership & Governance

Supporting Decision-Makers Professionally — and Serving as One

President · The Georgian Condominium Unit Owners’ Association

2026–Present · Treasurer 2023–2026 · Washington, DC

Lead governance and operations for a self-managed condominium association, coordinating board priorities, vendor matters, owner communications, compliance records, and financial oversight.

As Treasurer, implemented PayHOA, led a banking transition, strengthened owner-account documentation and payment tracking, and prepared board-facing financial and governance records—including a $34,500 FY2026–2027 proposed budget.

Board service adds a useful perspective to my professional work: I understand the value of support not only from the person providing it, but also from the decision-maker relying on it.

Education

Liberty University

B.S. Candidate, Paralegal Studies
Expected December 2026

GPA 3.7Dean’s List · Spring 2023

Contact

Interested in What I Could Bring to Your Team?

I am interested in Legal Operations, Executive Support, Administrative Operations, Governance, and related roles where judgment, process discipline, leadership support, and operational improvement are part of the same function.

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