Summary
Overview
Work History
Education
Skills
Timeline
Generic

DYLAN BENSON

Gloucester

Summary

Results-driven legal and claims professional with over 10 years of experience in municipal law, higher education, and public service. Skilled in professional liability, insurance claims coordination, contract review, and risk management. Adept at handling sensitive litigation matters, drafting and reviewing legal documents, and coordinating with outside counsel, insurers, and regulatory agencies. Known for strong judgment, analytical ability, and attention to detail in managing complex claims, compliance issues, and deadlines. Proven success supporting general counsel and senior leadership with case strategy, policy development, and resolution of high-exposure liability matters.

Overview

14
14
years of professional experience

Work History

Paralegal

Brandeis University, Office of the General Counsel
06.2025 - Current
  • - Provide comprehensive legal and claims support to university counsel, including drafting and reviewing contracts, compliance reports, and insurance-related documents.
  • - Investigate and coordinate responses to liability claims, subpoenas, and regulatory inquiries, collaborating with insurers and outside counsel to assess exposure and ensure timely resolution.
  • - Manage litigation calendars, including discovery deadlines, regulatory filings, and depositions, while monitoring risk across employment, contract, and intellectual property disputes.
  • - Prepare board-level reports and training materials on compliance, risk management, and legal exposure.
  • - Maintain secure case files and document systems in compliance with institutional retention and confidentiality standards.
  • - Provide comprehensive legal and administrative support to university counsel, including drafting and proofreading contracts, compliance documents, and internal correspondence.
  • - Conduct legal research on issues related to higher education, employment law, risk management, intellectual property, and licensing.
  • - Manage complex legal calendars, including litigation deadlines, contract renewals, and regulatory filing schedules; coordinate attorney meetings, depositions, and internal briefings.
  • - Maintain organized and secure case files, both digital and physical, in compliance with institutional retention policies.
  • - Serve as primary point of contact for office-wide scheduling, including coordination of meetings across departments, external counsel, and outside agencies.
  • - Support the General Counsel with preparation of board materials, policy development, and internal training sessions.
  • - Oversee daily office operations including matter intake tracking, legal billing coordination, document workflows, and intern onboarding.
  • - Facilitate communication and collaboration across departments on matters involving contracts, compliance, real estate, and governance.
  • - Coordinate responses to subpoenas, public records requests, and regulatory agency inquiries.

Ward 2 City Councilor

City of Gloucester
01.2024 - Current
  • - Provide constituent services and resolve community concerns with effective solutions.
  • - Draft, review, and amend ordinances to align with community needs and legal standards.
  • - Review zoning and land use matters, granting permits and engaging with stakeholders on development projects.
  • - Lead communications strategy for campaign and office, producing press releases, newsletters, and public statements.
  • - Provided constituent services, addressing local concerns with prompt resolutions.
  • - Crafted and amended city ordinances, ensuring alignment with community needs.
  • - Negotiated and approved the city budget, allocating resources effectively.
  • - Created and modified zoning laws to support sustainable urban development.
  • - Led all communications strategy for campaign and public office, including writing press releases, email updates, and social media content to engage constituents and promote transparency.
  • - Managed public messaging and branding across platforms, using Canva and Mailchimp to produce visual content and newsletters.
  • - Delivered speeches and public statements to communicate policy changes and city updates to a broad community audience.
  • - Review and vote on zoning and land use matters; grant special permits for property development and use changes; engage with constituents, developers, and city planners on real estate projects.
  • - Collaborate on policy related to housing, land use, and infrastructure, ensuring compliance with local ordinances and state regulations.

Law Clerk

City of Beverly
05.2019 - 06.2025
  • - Managed legal operations for the City Solicitor's Office, ensuring efficient workflows and compliance.
  • - Drafted and reviewed liability claims, motions, and ordinances; coordinated closely with city officials, insurers, and counsel.
  • - Conducted research and prepared memoranda on complex municipal law issues, collective bargaining, and employment law.
  • - Collaborated with insurance carriers to resolve liability and property claims, assessing exposure and compiling evidence.
  • - Drafted legal opinions, policy memos, and governance documents for presentation to City Council and Mayor.
  • - Managed legal operations for the City Solicitor's Office, ensuring efficient workflows across departments and timely compliance with legal requirements.
  • - Reviewed and drafted legal documents including liability claims, motions, depositions, and land use ordinances; coordinated closely with city officials, insurers, and external counsel on real estate and regulatory matters.
  • - Conducted legal research and developed clear, data-driven memoranda and presentations on complex municipal issues.
  • - Negotiated collective bargaining agreements, represented city interests in employee relations, and ensured compliance with state and federal labor laws.
  • - Maintained and monitored critical legal deadlines to avoid compliance lapses and minimize exposure.
  • - Collaborated with insurance carriers to resolve property and liability claims, compiling evidence, coordinating across departments, and assessing risk exposure.
  • - Assisted with preparation of legal opinions and presentations to City Council and Mayor, supporting decisions on contracts, labor disputes, zoning changes, and litigation strategy.
  • - Drafted and edited ordinance amendments, official responses, and internal governance documents in line with public records and legal standards.
  • - Oversaw citywide legal communications, including press releases, policy memos, and attorney-client privileged correspondence.
  • - Maintained secure legal databases and document systems, tracked case milestones, and onboarded new legal staff and interns.

Intern

Worcester Court Service Center
01.2019 - 05.2019
  • - Supported supervising attorneys in various legal tasks and case management.
  • - Assisted litigants in filling out court forms, providing clear guidance on legal procedures.
  • - Affecting homeless children and their families. Volunteered in local homeless shelters, working directly with children.
  • - Facilitated access to interpreter services, ensuring accurate communication during legal proceedings.

Graduate Assistant

Anna Maria College
10.2018 - 05.2019
  • - Taught college preparation courses to high school students, focusing on academic readiness.
  • - Mentored students on SAT preparation and organized college-related events.
  • - Provided students with general college information and guidance on applications.

Community Organizing Intern

Massachusetts Coalition for The Homeless
09.2017 - 05.2018
  • - Conducted research on policy proposals aimed at supporting homeless individuals.
  • - Recruited organizations to endorse the Coalition's legislative proposals.
  • - Mobilized community members, resulting in [X] letters sent to legislators in support of key policy campaigns.

Pre-Legal Intern

Children's Law Center of Massachusetts
05.2017 - 06.2017
  • - Conducted legal research in educational law, immigration law, and disability law.
  • - Assisted in tracking the development of specific cases and provided support during client meetings.
  • - Drafted, reviewed, and revised legal documents, contributing to case preparation.

Intern

Attorney General's Office
01.2017 - 04.2017
  • - Assisted the trial division office with legal research and memo creation.
  • - Collaborated with legal interns and paralegals on various projects for the trial division.

Intern

Salem District Court
07.2016 - 12.2016
  • - Observed court trials and assisted in trial court office tasks.
  • - Supported state police with motor vehicle hearings.

Campaign Manager

Greg for Mayor
04.2015 - 09.2015
  • - Organized fundraising events, boosting campaign donations by 40%.
  • - Managed community outreach efforts and volunteer coordination.
  • - Ran all social media outlets, enhancing campaign visibility and engagement.

Deputy Campaign Manager

Kirk for Mayor
07.2013 - 11.2013
  • - Conducted opposition research and coordinated volunteer activities.
  • - Facilitated communication between the campaign and the press, ensuring accurate media coverage.

Intern

Office of Mayor Carolyn Kirk
08.2011 - 11.2011
  • - Coordinated community outreach initiatives and supported the Mayor on various tasks.

Education

Master Certificate - International Relations

Northeastern University
Boston, MA
12.2021

Master of Criminal Justice - undefined

Anna Maria College
Paxton, MA
07.2019

Bachelor of Criminal Justice - International Relations

Salem State University
Salem, MA
08.2017

Skills

  • Legal research and writing, document drafting and handling, contract review and compliance, insurance claims and liability coordination, subpoena and records response, litigation support, public records and FOIA compliance, workflow oversight, scheduling and deadline tracking, onboarding and training, cross-functional communication, Microsoft Office Suite, SharePoint, Teams, Zoom, case and document management systems
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Timeline

Paralegal

Brandeis University, Office of the General Counsel
06.2025 - Current

Ward 2 City Councilor

City of Gloucester
01.2024 - Current

Law Clerk

City of Beverly
05.2019 - 06.2025

Intern

Worcester Court Service Center
01.2019 - 05.2019

Graduate Assistant

Anna Maria College
10.2018 - 05.2019

Community Organizing Intern

Massachusetts Coalition for The Homeless
09.2017 - 05.2018

Pre-Legal Intern

Children's Law Center of Massachusetts
05.2017 - 06.2017

Intern

Attorney General's Office
01.2017 - 04.2017

Intern

Salem District Court
07.2016 - 12.2016

Campaign Manager

Greg for Mayor
04.2015 - 09.2015

Deputy Campaign Manager

Kirk for Mayor
07.2013 - 11.2013

Intern

Office of Mayor Carolyn Kirk
08.2011 - 11.2011

Master of Criminal Justice - undefined

Anna Maria College

Bachelor of Criminal Justice - International Relations

Salem State University

Master Certificate - International Relations

Northeastern University

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