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Senior Corporate Paralegal

Remote - USA, CAN, MEX

A little about us…Fleetio is a modern software platform that helps thousands of organizations worldwide manage their fleet operations. Transportation technology is a hot market, and we’re leading the charge with raving fans and new customers signing up every day. We raised $450M in our Series D funding round in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

Description

We are actively seeking a Senior Corporate Paralegal to join our Legal team. As a Senior Corporate Paralegal, you will play a key role in ensuring the efficient and effective delivery of services by the Legal Department. You will independently manage a broad range of legal matters, with a significant emphasis on commercial contracts, legal operations, and cross-functional partnership.

The ideal candidate is an experienced corporate paralegal who is comfortable exercising independent judgment, managing competing priorities, and taking ownership of projects from start to finish. You are detail-oriented, highly organized, comfortable with change, and a proactive problem solver who looks for opportunities to improve how the Legal team operates.

Reporting to the Head of Legal, you will work closely with attorneys, the corporate paralegal and business stakeholders throughout Fleetio and will have significant responsibility for helping the Legal Department scale alongside a growing company.

Who You Are

You are a very experienced in-house corporate paralegal who can independently handle a broad range of legal and operational matters. You have substantial experience drafting, reviewing, redlining, and negotiating commercial agreements and are comfortable working directly with business stakeholders to move matters toward resolution.

You understand when you can independently resolve an issue and when a matter should be escalated to an attorney. You are also someone who takes ownership of processes—not simply following established workflows, but identifying opportunities to make them more efficient, consistent, and scalable.

You are a career paralegal.

Your Impact

  • Independently review, draft, populate, redline, and negotiate a variety of commercial agreements, including MSAs, non-disclosure agreements, statements of work, amendments, order forms, vendor agreements, and other customer and supplier agreements.
  • Manage contract matters from intake through execution, working directly with internal stakeholders, counterparties, and attorneys to efficiently move agreements to completion.
  • Serve as a trusted Legal Department resource for internal business teams regarding contracts, contracting processes, vendor and supplier matters, and other routine legal matters.
  • Identify contractual issues and deviations from Fleetio's standard positions, independently resolve routine issues within established guidelines, and appropriately escalate legal or business risks requiring attorney review.
  • Take ownership of assigned legal workflows and processes, including developing and maintaining templates, playbooks, procedures, and other resources that enable the Legal Department and its business partners to operate efficiently.
  • Partner with attorneys and business stakeholders to develop and implement scalable contracting processes, approval workflows, and escalation procedures.
  • Work as a change agent to continuously improve Legal Department operations by assessing existing policies, procedures, technology, workflows, and program effectiveness and recommending and implementing improvements.
  • Manage and maintain contract lifecycle management and other Legal Department technology, including helping develop workflows, reporting, templates, and processes that improve adoption and efficiency.
  • Assist with monitoring contractual obligations, renewals, amendments, and other significant contract requirements.
  • Maintain and assist with corporate governance records, corporate filings, policies, and other corporate records.
  • Support compliance initiatives and other cross-functional Legal Department projects as needed.
  • Prepare correspondence and other documentation in support of Legal, Sales, Finance, Procurement, and other business functions.
  • Serve as a resource to other members of the Legal team, including providing guidance, training, and support on contracting processes, legal technology, and departmental procedures.
  • Help develop training materials and provide training to business stakeholders regarding contracting processes and other Legal Department procedures.
  • Assist with special projects and other legal matters as the needs of the company and the Legal Department evolve.
  • Other duties as assigned.

Your Experience

  • Minimum of 6 years of relevant paralegal experience, including substantial in-house experience supporting corporate and commercial legal matters.
  • Significant hands-on experience reviewing, drafting, redlining, and negotiating commercial contracts with limited attorney supervision.
  • Experience managing contract matters directly with business stakeholders and, where appropriate, external counterparties.
  • Demonstrated ability to distinguish between matters that can be handled independently and issues requiring attorney escalation.
  • Experience designing, implementing, or materially improving legal workflows, contracting processes, templates, playbooks, or other Legal Department procedures.
  • Strong project management skills and demonstrated ability to independently manage multiple matters and competing priorities in a fast-paced environment.
  • Excellent written and verbal communication skills and the ability to communicate effectively with attorneys, business stakeholders, and external parties.
  • Strong attention to detail combined with the ability to understand broader business objectives and apply practical judgment.
  • Demonstrated ability to handle highly confidential and sensitive information.
  • Ability to work effectively both independently and collaboratively as part of a team.
  • Bachelor's or associate degree required. A paralegal certificate is considered a plus but not required with appropriate experience.
  • Proficiency with Microsoft Office, Google Workspace, Adobe Acrobat Pro, and electronic signature platforms such as DocuSign.
  • Experience with contract lifecycle management, legal operations, project management, and business systems such as Ironclad, Jira, and Salesforce is preferred.
  • Comfortable adopting new technology, including AI-enabled legal tools, and helping implement technology and process improvements.
  • Considered a plus: experience working in an in-house Legal Department, particularly at a SaaS or other technology company.

 

Benefits 

  • Multiple health/dental coverage options (100% coverage for employee, 50% for family)
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks (increases at year two!)
  • 12 company holidays + 2 floating holidays
  • Parental leave - birthing parent (16 weeks paid) non-birthing (4 weeks paid)
  • FSA & HSA options
  • Short and long term disability (short term 100% paid)
  • Community service funds
  • Professional development funds
  • Wellbeing fund - $150 quarterly
  • Business expense stipend - $125 quarterly
  • Mac laptop + new hire equipment stipend
  • Fully stocked kitchen with tons of drinks & snacks (BHM only)
  • Remote working friendly since 2012 #LI-Remote

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

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We use AI-assisted tools to support our application review process. These tools help us assess qualifications and assist our recruiting team in identifying candidates whose skills and experience closely match the job requirements we selected for this role. If you’d prefer to opt out of profiling, you can contact us at recruiting@fleetio.com, and we’ll review your application without AI assistance.

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