Open Positions

Litigation Attorney 
Portland, Maine

At Drummond Woodsum, we pride ourselves on being more than just another law firm. We understand that our people are our greatest asset, which is why we’ve intentionally cultivated an environment that promotes personal and professional growth through challenging and interesting work and mentorship, fosters a supportive team atmosphere, recognizes the importance of a healthy work-life balance, and offers benefits that reflect our genuine care for our colleagues.

We seek an experienced litigator to join the Trial Services Group in our Portland, Maine office. If you bring at least 3 years of litigation experience and are passionate about advocacy, we want to hear from you!

This is a general litigation role but will primarily consist of construction, real estate, commercial, and probate cases. In this role, you will work closely with other skilled litigators and subject matter experts across practice groups, collaborating on the complex legal issues that arise in these cases from the start of a dispute, to trial, and on appeal. You will have the opportunity to showcase your expertise with clients, other practitioners, and in the courtroom.

If you have top-notch research, writing, and oral advocacy skills, a passion for the law, a strong work ethic, a desire to work closely with others, exceptional client relation skills, and impressive academic credentials, we encourage you to apply. Experience in handling discovery, motion practice, and oral advocacy is necessary and Maine bar admission is strongly preferred.

If this sounds like the opportunity you’ve been waiting for, we invite you to submit a letter of interest and your resume to hr@dwmlaw.com. No phone calls, please. All inquiries are held in the strictest of confidence. We look forward to hearing from you.

We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Hybrid office option
• Professional development, including costs for dues and continuing education
• Firm involvement
• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

Bankruptcy, Restructuring & Creditors’ Rights Attorney 
Portland, Maine 

At Drummond Woodsum, we pride ourselves on being more than just another law firm. We understand that our people are our greatest asset, which is why we’ve intentionally cultivated an environment that promotes personal and professional growth through challenging and interesting work and mentorship, fosters a supportive team atmosphere, recognizes the importance of a healthy work-life balance, and offers benefits that reflect our genuine care for our colleagues.

Drummond Woodsum seeks an associate attorney to join its Bankruptcy, Restructuring & Creditors’ Rights team in its Portland, Maine office. While seated within the Trial Services Group, this position blends both litigation and general corporate representation on behalf of a wide array of financial institutions throughout Northern New England.

This role is ideal for an attorney with a strong foundation or interest in litigation, whether gained in a law firm, government practice, or through clerking, who is eager to specialize in bankruptcy, restructuring, and creditors’ rights. As part of our team, you will be involved in a wide range of litigation and advisory matters, including representing debtors, creditors, and other parties in bankruptcy proceedings, representing creditors in commercial and consumer foreclosure and collection matters, advising clients on regulatory compliance and other best practice matters, advising clients on restructuring strategies, handling complex litigation related to bankruptcy and creditors’ rights, and participating in cases in Federal, State, and Tribal courts, as well as before administrative agencies and arbitration panels.

What sets Drummond Woodsum apart is our collaborative approach. Our attorneys work closely across practice areas, leveraging collective expertise to tackle complex legal challenges. Our litigation team handles a broad spectrum of cases, providing you with exposure to a variety of substantive legal matters. We are committed to the personal and professional development of our attorneys, offering guidance and a cohesive team environment.

If you have top-notch research, writing, and oral advocacy skills, a passion for the law, a strong work ethic, a desire to work closely with others, exceptional client relation skills, and impressive academic credentials, we encourage you to apply. Admission to the Maine bar is strongly preferred.

If this sounds like the opportunity you’ve been waiting for, we invite you to submit a letter of interest and your resume to hr@dwmlaw.com. No phone calls, please. All inquiries are held in the strictest of confidence. We look forward to hearing from you.

We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Hybrid office option
• Professional development, including costs for dues and continuing education

Firm involvement including:

• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

Litigation Paralegal
Portland, Maine 

Drummond Woodsum is seeking a full-time Litigation Paralegal to join our firm’s Trial Services Group working in Portland, Maine. Our litigation team is involved in a wide array of civil litigation matters in federal and state courts and administrative agencies, and is involved in cases including personal injury (Plaintiff and Defendant), bankruptcy, medical malpractice, civil rights claims against public schools, municipalities, and public officials, land use matters, and employment disputes, among others. As a paralegal in this role, you’ll support attorneys by providing critical legal support including, but not limited to, drafting pleadings, discovery requests, and motions, organizing and analyzing documents, and enhancing the overall efficiency of our legal team. While prior litigation experience is a plus, it is not a necessity for this role.

Responsibilities include:

• Assisting attorneys with discovery, trial, and hearing preparations, including attending trials and panel hearings
• Assist at trial or panel hearing as a trial tech utilizing Trial Director or other trial presentation software
• Conducting , medical, expert, social media, and other research  to  gather relevant information for cases
• Liaising with court officials, opposing counsel, and other parties as needed
• Possessing strong writing, analytical and verbal communication skills, excellent spelling, punctuation, and grammar skills ??move to qualifications list below
• Preparing initial drafts of pleadings and documents as directed by attorneys, processing edits and redlining in Word, and conversions and manipulations in PDF
• Communicating with clients and providing exceptional service
• Extensive document review, organization and analysis of *discovery material and digesting of information contained therein or …discovery material including medical records, business records, employment and other documents obtained in discovery
• Experience with or willingness to learn eDiscovery software for management and review of large document cases
• Additional duties as assigned

Qualifications:

• Strong writing skills, including drafting documents, pleadings, correspondence, and reports, with attention to detail in spelling, grammar, and punctuation
• Strong organizational abilities to manage multiple tasks, deadlines, and case files efficiently
• Excellent verbal and written communication skills for interacting with clients, attorneys, court personnel, and colleagues
• System proficiency: general knowledge and experience with common software applications, such as Microsoft Office Suite and PDF processing; strong Excel and MS Word skills, in particular, are essential.
• Familiarity with trial presentation software and research sites, such as Westlaw, is helpful
• High level of accuracy and attention to detail in reviewing documents and managing case information
• Motivated to learn and provide work of the highest quality

At Drummond Woodsum we are committed to the growth and development of our employees.  Our focus is geared toward fostering a culture where you can work with and learn from diverse individuals, explore and expand your capabilities, and are valued for the contributions and perspectives you bring. We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Firm involvement, including:
• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

For consideration, please submit your resume and cover letter by email to hr@dwmlaw.com. We look forward to hearing from you.

Billing Administrative Assistant
Portland, Maine 

Drummond Woodsum is seeking a full-time Billing Administrative Assistant to join our team. This position is a full-time, hourly position that supports the Chief Financial Officer and back-office administration team. This role works with all members of the firm, including attorneys, staff, and clients, with a primary focus on supporting the administrative and billing objectives of the firm.

Responsibilities include:

• Invoice Preparation and Support
• Utilize the firm’s time and billing system to update invoices, including entering holds, write-offs, and edits.
• Process changes in the firm’s time and billing system.
• Prepare and generate client invoices based on time and expense entries.
• Prepare and generate invoices for DWM Subsidiaries.
• Ensure all invoices are accurate, complete, and comply with client agreements and firm policies.
• Ensure compliance with the firm’s billing procedures and guidelines.
• Review billing data for accuracy and completeness before finalizing invoices.
• Assigns internal inquiries related to billing in our email system to the appropriate team member.
• Sort pre-bills and provide clerical support to billing team.
• Processes and files mail.
• Semi-annual audit of client related records held in firesafe and recorded in time and billing software.
• Provide Managing Director weekly list of checks, ACHs, and wires from the client trust and operating account, independent of the finance/accounting team.
• Provides coverage for reception during receptionist’s scheduled breaks and time off.
• Provides second-tier coverage for conducting conflict of interest searches in firm database.
• Additional duties as requested.

Qualifications:

1. Minimum of high school diploma, with 1-3 years of experience preferred
2. Proficiency in Microsoft Office Suite (Excel, Word, Outlook).
3. Ability to build rapport with attorneys, professional staff, clients, and vendors.
4. Strong organizational skills with focus on attention to detail.
5. Self-motivated and ability to work autonomously.
6. Ability to listen, read, and understand information received verbally or written.

At Drummond Woodsum we are committed to the growth and development of our employees.  Our focus is geared toward fostering a culture where you can work with and learn from diverse individuals, explore and expand your capabilities, and are valued for the contributions and perspectives you bring. We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Firm involvement, including:
• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

For consideration, please submit your resume and cover letter by email to hr@dwmlaw.com. We look forward to hearing from you.

Legal Assistant 
Portland, Maine 

Drummond Woodsum is seeking a full-time legal assistant for our Business Services Group in our Portland, Maine office. This position entails carrying out administrative services, providing support to legal professionals by preparing various documents including correspondence, legal forms, and other types of documents, and support to enhance attorney/timekeeper effectiveness.

Responsibilities:

• Complete administrative duties, such as making copies, answering and directing phone calls, and greeting clients in a professional and courteous manner
• Prepare documents and forms by completing initial drafts, processing edits and red-lining in Word, and conversions and manipulations in PDF
• Handle incoming and outgoing mail
• Communicate with clients
• Keep files and corresponding deadlines organized and labelled
• Provide exceptional service to all clients
• Additional duties as assigned

Qualifications:

• Be accurate, detail-oriented, and have strong attention to detail
• Take initiative and be proactive; anticipate needs; reach out to become more involved
• Strong writing and verbal communication skills; excellent spelling, punctuation, and grammar skills
• System proficiency: general knowledge and experience with common software applications, such as Microsoft Office Suite and PDF processing; strong Excel and MS Word skills in particular
• Motivated to learn and provide work of the highest quality

At Drummond Woodsum we are committed to the growth and development of our employees.  Our focus is geared toward fostering a culture where you can work with and learn from diverse individuals, explore and expand your capabilities, and are valued for the contributions and perspectives you bring. We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Firm involvement, including:
• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

For consideration, please submit your resume and cover letter by email to hr@dwmlaw.com. We look forward to hearing from you.

IT Systems Administrator
Portland, Maine 

Drummond Woodsum is looking for a full-time IT Systems Administrator to join our team. This position reports directly to the Director of Information Technology and supports the Director and IT Manager in their efforts to maintain the integrity of the firm’s technological framework. The Systems Administrator is responsible for identifying network requirements, troubleshooting technical issues, managing system and application upgrades, and monitoring performance across all office locations. Occasional after-hours support may be required to address escalated issues.

Responsibilities include:

• Oversee network traffic and usage, identifying and resolving performance issues to ensure smooth operations. Analyze key performance metrics such as bandwidth, latency, and throughput, escalating problems to vendors when necessary. Troubleshooting slow connections, hardware malfunctions, and other network-related issues will be central to this role, with a focus on maintaining network security by monitoring for unauthorized access or suspicious activity.
• Master and maintain an efficient computer imaging system to streamline the deployment of new computers. This includes developing and optimizing imaging processes for quick, consistent installations across multiple devices, reducing setup time for new equipment. Regularly update and troubleshoot the imaging system to ensure it remains current with the latest software versions and security protocols. Collaborate with the IT team to improve deployment strategies and document procedures for seamless onboarding of new hardware.
• Maintain and troubleshoot M365 tenant configurations and policies. Monitor system performance, generate reports, manage updates, and work with the IT team to ensure the M365 environment meets organizational needs and compliance requirements.
• Partner with vendors to ensure devices are encrypted, equipped with up-to-date virus protection, and regularly patched. Implement and manage appropriate monitoring tools to maintain system performance and security, ensuring all devices adhere to organizational standards for security and efficiency.
• Responsible for the maintenance, upgrading, and monitoring of major applications within the organization. This role involves ensuring optimal performance and availability of critical systems by implementing updates, troubleshooting issues, and performing regular system audits. The administrator will collaborate with cross-functional teams to deploy application enhancements, manage user access, and ensure security protocols are followed. Additionally, the role requires proactive monitoring of application performance, analyzing system metrics, and providing timely support to resolve incidents.
• Collaborate with the Director of Information Technology and external vendors to support risk assessments and penetration testing efforts. Analyze test results and implement corrective actions to enhance system defenses. Maintain comprehensive documentation of risk assessments, test outcomes, and mitigation strategies to ensure a proactive approach to cybersecurity.
• Create, improve, maintain, and ensure accessibility of various internal documents to support the efficient and secure operation of IT systems, mitigate risks, and facilitate compliance.
• Gather information to support the development of the departmental budget and collaborate with internal departments to understand their IT needs and provide solutions. Conduct cost-benefit analyses for employee requests to ensure effective support for day-to-day operations.

Qualifications:

• An undergraduate degree in Information Technology or 5 years of broad-based information technology experience with a law firm or similar service-based organization is preferred.
• Demonstrated and/or the ability to develop supervisory skills. Strong leadership and team management skills, with the ability to motivate and guide a technical team effectively.
• Strong customer service, interpersonal, and communication skills, with the ability to collaborate effectively across different teams and departments.
• High degree of initiative, exercising independent judgment, and managing multiple priorities in a fast-paced, deadline-driven, detail-oriented work environment; ability to function in stressful situations and think strategically and analytically to troubleshoot and resolve issues quickly.
• Ability to translate information related to current and new technology and telecommunication hardware, systems, and processes to all levels of internal staff. Ability to interact credibly and diplomatically and to lead through influence.
• Demonstrated experience with or ability to manage contract negotiation, understanding statements of work and contract language.
• Good understanding and technical knowledge of current computer systems (hardware/software), networks, security, telecommunications, databases, and storage systems.
• Engage in ongoing learning of the latest technologies and trends by participating in educational opportunities, reading professional publications, maintaining personal networks, and being active in professional organizations.

At Drummond Woodsum we are committed to the growth and development of our employees.  Our focus is geared toward fostering a culture where you can work with and learn from diverse individuals, explore and expand your capabilities, and are valued for the contributions and perspectives you bring. We’re committed to providing our team members with the support they need to thrive both personally and professionally, and we are proud to offer the following benefits:

• Insurance options, including domestic partner coverage, for health (either a co-pay-based plan or HSA with firm contributions), dental, and vision
• 401(k) plan with pre- or post-tax investment options and firm contributions
• Wellness support, including partnerships with SoulBeing and Calm, telehealth coverage, and on-site privacy rooms
• Life insurance coverage at 1.5x your annual salary, plus supplemental voluntary coverage available
• Leave plans, including paid parental leave, short- and long-term disability
• Firm involvement, including:
• Monthly firm lunch meetings to hear about all areas of the firm
• Committee participation, such as our Community Service Committee which organizes a drive every December and our public outreach week in July
• Social gatherings – 2023 included a field day BBQ, a holiday get-together, and our annual Halloween party for our families

For consideration, please submit your resume and cover letter by email to hr@dwmlaw.com. We look forward to hearing from you.