Top 4 Senior paralegal Jobs in Annapolis, Md

Senior Paralegal | Rimmon Hill LLC ($80,000 - $100,000)
Bruiser Holdings LLC —Annapolis, MD
- $80,000 - $100,000 a year
- Full-time
- Mid-level
- Organizational skills
- In-person
- Profit sharing
- Health insurance
Quick Apply
13d
Senior FOIA Paralegal
Contact Government Services, LLC —Baltimore, MD
- $65,357.76 - $94,405.65 a year
- Full-time
- Hybrid work
- Word processing
- English
- Mid-level
- Health insurance
- Dental insurance
Quick Apply
Tax Senior, Legal Business Services - Technology
Deloitte —Baltimore, MD
- $100,350 - $205,000 a year
- Full-time
- Hybrid work
- CPA
- Up to 50% travel
- 3 years

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Senior Paralegal | Rimmon Hill LLC ($80,000 - $100,000)

Bruiser Holdings LLC
Annapolis, MD

Quick Apply

Job Details

Full-time
$80,000 - $100,000 a year
13 days ago

Benefits

Profit sharing
Health insurance
Dental insurance
401(k)
Paid time off
401(k) 4% Match
Vision insurance
401(k) matching
Life insurance
Paid sick time

Qualifications

Civil litigation support
Executive administrative support
Attention to detail
Organizational skills
Working as an executive assistant
Paralegal experience
Paralegal Certificate

Full Job Description

Senior Paralegal Assistant | Bruiser Companies

Where: Annapolis, MD 21402 - In-Office Position

Compensation: $80,000 - $100,000

Executive Support & Legal Operations

Join a fast-growing conglomerate at a critical moment. You'll work directly with the President of Bruiser Companies from our Annapolis office, operating at the intersection of legal compliance, human resources, and executive operations. This is a role where you'll see direct impact, your decisions and organization directly influence how we scale across five operational brands and 125+ employees throughout the region.

About Rimmon Hill LLC

Rimmon Hill LLC is a specialized real estate law firm based in Annapolis, Maryland, handling hundreds of litigation actions annually across tax lien foreclosures, landlord-tenant disputes, HOA law, real estate transactions, and title work. As Senior Paralegal Assistant, your primary focus will be supporting Rimmon Hill's legal operations and firm leadership. Rimmon Hill operates as part of Bruiser Companies, a rapidly expanding conglomerate with diverse revenue streams spanning trucking, auto care, towing, technology, and other operations. Since launching in 2023, Bruiser has grown to over $15 million in gross revenue.

What You'll Do

Your responsibilities will span legal operations, HR management, and executive administration. All reporting directly to the President.

Legal & Compliance

● Assist General Counsel with small claims complaints and legal filings

● Monitor case filings and respond to registered agent issues

● Coordinate with Maryland office on matters requiring President attention

● Advise President on annual HR compliance requirements and run quarterly internal audits

Human Resources & Operations

● Monitor company accounts weekly and manage incoming/outgoing payments

● Support President with scheduling, administrative tasks, and operational coordination

● Communicate effectively across teams and external partners

● Identify and solve problems with bias for action

What We're Looking For

● Paralegal certification or relevant legal environment experience

● Strong organizational skills and meticulous attention to detail

● Excellent communication and interpersonal abilities

● Proficiency with Excel, email, Google Suite, and modern business tools

● Ability and willingness to wear multiple hats in a small, dynamic team

● Trustworthiness and discretion (you'll have access to sensitive information)

● Willingness to audit frequently and challenge inconsistencies between metrics and reality

Work Environment & Logistics

Full-time, in-office position in Annapolis, Maryland. Willingness to increase hours during peak operational periods.

Compensation & Benefits

● Competitive salary: $80,000–$100,000 (commensurate with experience)

● 401(k) with 4% employer match

● Paid Time Off: 0.04 hours per hour worked

● Health, dental, and vision insurance

● Life insurance with $25,000 benefit

● Bonus and profit-sharing opportunities

This is an opportunity to build something meaningful. You'll have direct visibility into how your work scales a growing company, and you'll play a key role in our success. No task is beneath you. Ownership of outcomes matters more than titles.

Apply now and let's talk about how you can make an impact!

http://rimmonhill.com

Pay: $80,000.00 - $100,000.00 per year

Benefits:

401(k)
401(k) matching
Dental insurance
Health insurance
Life insurance
Paid sick time
Paid time off
Profit sharing
Vision insurance

Application Question(s):

This position requires full-time, in-office work at our Annapolis office. Are you currently located within a 30-minute commute of Annapolis, Maryland?
How many years have you worked as a paralegal or in a paralegal-level role?

Experience:

Paralegal: 3 years (Required)

Work Location: In person

Quick Apply

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senior paralegal jobs in annapolis, md

Senior Paralegal | Rimmon Hill LLC ($80,000 - $100,000)

Senior FOIA Paralegal

Tax Senior, Legal Business Services - Technology

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