Senior Paralegal/Executive Assistant

Casper Mehlos Law Group, LLC; Madison (WI); Hybrid; USD 75,000 - 110,000; Full time

Benefits offered by this job

Premium health insurance

401(k) plan with firm matching

Generous PTO and holidays

Hybrid work option

Job summary

Casper Mehlos Law Group, LLC in Madison, WI seeks a proactive Supervising Paralegal / Executive Assistant to lead operations, streamline workflows, mentor staff, and optimize legal tech systems in collaboration with firm leadership. This role emphasizes client-focused support and efficiency.

The ideal candidate is a self-starter with top-level attention to detail, strong analytical and communication skills, and experience supervising legal support staff.

Qualifications

• Demonstrated history of assisting attorneys in delivering exceptional client representation.
• Driven self-starter with ownership to manage, execute, and plan complex tasks without constant direction.
• Exceptional analytical skills with a passion for solving challenges and implementing innovative solutions.
• Outstanding time management and prioritization in a fast-paced setting.
• Excellent written and oral communication skills with clients in crisis.
• Experience supervising support staff to foster independence and accountability in a growth culture.
• Hands-on experience with legal tech/CRMs (Clio, Lawmatics) and MS Office Suite.

Responsibilities

• Assist attorneys with proactive workflow management, document production, scheduling, e-mail coordination for CEO, and litigation preparation to ensure elite-level client representation.
• Operational Execution: Manage scheduling, deadline tracking, email management, and administrative triage with urgency.
• Staff Leadership & Development: Supervise and mentor a team of legal support staff, monitoring KPIs, cultivating ownership mindset.
• Systems & Technology Optimization: Utilize and manage practice management platforms (Clio, Lawmatics, or other CRM systems) and office software to drive efficiency.
• Client Relationship Management: Serve as a compassionate, reassuring point of contact for clients navigating high-stakes criminal challenges while triaging multiple demands.
• Assist with firm financial workflows, including accounts payable, accounts receivable, and billing tracking as needed.

Skills

Leadership

Mentoring

Time management

Attention to detail

Communication

Empathy

Problem solving

Self-starter

Ownership

Tools

Clio

Lawmatics

CRM systems

Microsoft Office

Job description

Are you an extremely high-performing professional with exceptional organizational skills, drive, and initiative who thrives in a fast-paced environment?

Are highly motivated to work extremely hard alongside an executive team of lawyers who relentlessly pursue transformational growth to achieve the best possible results in our clients’ cases while achieving performance metrics at our high-performing growth law firm?

Do you have exceptional leadership skills that will allow you to mentor, empower, and help transform support staff into self-managed top performers in a metrics-driven, performance-incentivized growth culture while building empathetic connections with clients facing oftentimes life-altering criminal allegations during some of the most stressful moments of their lives?

Are you motivated by the opportunity to join a growth-driven criminal defense firm in Madison, WI, that is relentlessly committed to personal, professional, and team transformational growth?

If you answered YES to all questions, we would like you to apply for this position.

We believe in acquiring and rewarding top talent with a competitive package that reflects our commitment to our team’s shared success:

Salary:Highly competitive base salary based on professional experience.

Bonuses:Quarterly performance-based bonus structure linked to firm and individual performance metrics.

Health & Wellness:Premium medical insurance coverage, including highly competitive out-of-

network coverage.

Retirement:401(k) plan with firm matching contributions.

Paid Time Off:Generous PTO and holiday schedule.

Workplace:Modern office environment in Madison, WI. This is an in-office position though

partial work-from-home/hybrid option will be considered for the right candidate.

Our Firm

We are a transformative growth criminal defense law firm based in Madison, Wisconsin serving our clients statewide. We dedicate our professional lives to providing results-driven client representation. Our firm is built on the foundation of our transformative growth culture, expecting each team member to commit themselves to transformative professional growth to impact results in our clients’ cases, and ultimately our personal and professional commitment to make a life-changing impact in our clients’ lives whenever possible.

We execute our vision through living our four core values: embodying transformative growth mindset to achieve our full potential and reset the standards for what is possible; exhibiting an ownership-driven mentality that creates both accountability and opportunity through each member of our team owning their role in our clients’ and team’s success; making decisions that create three-way winners among our clients, our team members and our team; and utilizing collaborative problem-solving to achieve successful outcomes when tackling the most difficult challenges.

For this position, we are seeking a proactive, exceptionally motivated, high performing, high attention-to-detail, Supervising Paralegal / Executive Assistant to serve as a pivotal operational lead in our practice. In this role, you will collaborate closely with our firm’s leadership team to streamline operations, implement team metric tracking (key performance indicators), mentor support staff, optimize legal technology systems, perform legal work at a high level, and collaborate with our team to deliver an extraordinary client experience.

The ideal candidate is an independent self-starter who excels at triaging variable priorities, proactively solving complex operational and case-related challenges, utilizes extremely high attention-to-detail and advanced critical thinking skills, and exhibits the rare qualities necessary to achieve a collaborative team transformational growth culture.

Key Responsibilities

• Assist attorneys with proactive workflow management, document production, scheduling, e‑mail coordination for CEO, and litigation preparation to ensure elite‑level client representation.
• Operational Execution: Manage scheduling, deadline tracking, email management, and administrative triage with urgent.
• Staff Leadership & Development: Supervise and mentor a team of legal support staff, monitoring team and team member key performance indicators, cultivating an ownership mindset among our team members, and guiding them to become self‑managed, high‑performing employees.
• Systems & Technology Optimization: Utilize and manage practice management platforms (Clio, Lawmatics, or other CRM systems) and office software to drive efficiency.
• Client Relationship Management: Serve as a compassionate, reassuring point of contact for clients navigating high‑stakes, emotionally charged criminal legal challenges while efficiently triaging multiple simultaneous demands, oftentimes involving time constraints.
• Assist with firm financial workflows, including accounts payable, accounts receivable, and billing tracking as needed.

Position Requirements

• Embody our core values, particularly our transformative growth mindset to upskill your own ability to best serve our company and clients so that we can fulfill our mission of making life-changing impacts in our clients’ lives whenever possible.
• Demonstrated history of assisting attorneys in delivering exceptional client representation. If you do not have legal experience, but believe you have a truly exceptional skill set that would qualify you for this position, you will need to explain why we should hire you over a qualified candidate with advanced legal experience.
• Must be a driven self-starter who takes ownership to manage, execute, and plan complex tasks without needing constant direction.
• Exceptional analytical skills with a passion for taking on challenges and implementing innovative solutions.
• Outstanding attention to detail, time management, and the ability to prioritize dynamically in a fast-paced setting.
• Exceptional written and oral communication skills, with a natural ability to connect empathetically with clients in crisis.
• Experience supervising support staff to foster independence and accountability in a high-performing, metrics-driven growth culture.
• Hands-on experience with legal tech/CRMs (Clio, Lawmatics, etc.) and mastery of Microsoft Office Suite (Word, Excel, PowerPoint).
• A continuous growth mindset and dedication to creating "three-way winners."

Preferred / Plus Qualifications

• Finances:Experience managing law firm financial tasks (AP/AR, billing).
• Bilingual:Fluency in Spanish.
• AI Technology/Automation: Experience building autonomous agents through Claude and creating automation workflows through Clio software.