Dakota Group is hiring 3 to 5 remote Contract Compliance Filing Specialists to support seasonal filing volume and continued growth across our compliance operations team.
This is a full-time contract opportunity for individuals who are comfortable working in a structured remote environment with tracked company equipment, clear daily deliverables, and performance measured through KPIs and SLAs. We are looking for detail-oriented, accountable team members who want to build real experience in compliance operations and grow into long-term opportunities within the company.
Who We Are
Dakota Group, through DakotaGroupUS.com, supports commercial vehicle operators and DOT holders with compliance filings, regulatory support, and related onboarding services. We help businesses operating commercial vehicles stay current with state and federal requirements through a combination of filing support, service operations, and client guidance.
Our team works directly with clients who need help navigating trucking compliance requirements and related filings. This includes support for required updates, renewals, enrollments, and time-sensitive forms that impact their ability to operate properly and remain in good standing.
We are a fast-moving, remote-enabled company that values responsiveness, accuracy, accountability, and internal growth. Team members are expected to perform at a high level, communicate clearly, and complete detailed work consistently throughout the day. In return, we provide structured training, clear expectations, measurable growth paths, and the opportunity to earn a full-time role with strong benefits.
Compensation and Opportunity
- $25 per hour
- 40 hours per week
- All equipment provided
- Federal holidays paid off
- Remote position
Strong performers may be promoted to full-time employment with access to a FT offer which includes:
- 401(k) with safe harbor match
- 50% company-paid benefits
- PTO
- Bonus eligibility
We provide exact performance expectations and clearly defined goals for teammates who want to earn full-time employment.
What the Role Involves
This role is centered on completing filings and compliance-related onboarding work on behalf of our clients. You will be responsible for processing detailed work accurately, following internal procedures, and helping ensure forms are completed properly and on time.
Core responsibilities include:
- Completing MCS-150 filings
- Completing UCR filings
- Supporting Drug and Alcohol Testing enrollment and onboarding
- Completing Form 2290 filings
- Assisting with other required state and federal forms
- Reviewing client-submitted information for completeness and accuracy
- Identifying missing or incorrect information
- Communicating internally regarding issues, escalations, and status updates
- Maintaining strong production and quality standards throughout the workday
This is a production-based compliance role. Candidates should be prepared to complete detailed filing work consistently during working hours and perform in an environment where output, accuracy, responsiveness, and adherence to process matter.
This role is best suited for someone who is comfortable with repetitive, detailed, deadline-driven work and who takes pride in accuracy and consistency.
You will be expected to:
- Learn and follow Dakota Group’s filing procedures and service standards
- Complete MCS-150 filings accurately and efficiently
- Process UCR filings with close attention to deadlines and detail
- Support Drug and Alcohol Testing enrollment tasks and related onboarding steps
- Manage work within required KPIs and SLAs
- Stay organized across multiple client files and priorities
- Work productively in a remote environment during scheduled hours
- Use company systems correctly and consistently
- Escalate issues when information is unclear, incomplete, or inconsistent
- Maintain professionalism when supporting internal teams and, over time, clients directly
As you develop in the role, there may be opportunities to grow into either:
- a Client Success role, helping clients resolve errors and complete requirements properly, or
- a Compliance Specialist role, focused on completing filings and operational work at a high level throughout the day
Training and Support: Training is provided through a structured onboarding and development process led by Dakota Group leadership and managers.
You will receive training from:
- The Director of Client Success & Training, managers across the business, and a strong rotational training program designed to give exposure to multiple workflows and management styles
This means you will not be trained by just one person. You will train with multiple managers so you can build a broader understanding of our services, internal standards, and client expectations. We want team members who are coachable, eager to learn, and ready to improve quickly.
Strong preference will be given to candidates with experience in:
- FMCSA compliance
- DOT compliance
- Tax preparation or tax operations
- Accounting
- Legal support or legal operations
- Government compliance work
Direct experience with trucking compliance is strongly preferred, but candidates with other compliance-heavy backgrounds may also be a strong fit.
Tools Used
- Zendesk
- HubSpot
- Google Suite
Skills We Value
- FMCSA Compliance
- DOT Compliance
- Tax, Accounting, or Law experience
- Strong attention to detail
- Ability to work independently in a remote environment
- Comfort with tracked systems and measurable performance expectations
- Strong written communication
- Reliability, consistency, and accountability
Why Join Dakota Group
We reward strong performance and create real internal growth opportunities for teammates who show they can handle responsibility, maintain quality, and contribute consistently. This is an opportunity to join a team that values operational discipline, detailed work, and long-term development.
If you are looking for a remote role where training is provided, expectations are clear, and strong performance can lead to a full-time career path, Dakota Group would like to hear from you.
