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⚖️Legal & Compliance
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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!
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.
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.
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.
Salary not disclosed for this role. See what similar remote roles pay →
Health Insurance
Dental Insurance
Vision Insurance
Flexible Spending Account (FSA)
Health Savings Account (HSA)
Disability Insurance
Life Insurance
Wellness Programs
Employee Assistance Program
401(k) / Retirement Plan
401(k) Match
Stock Options
Performance Bonus
PTO / Vacation
Paid Holidays
Bereavement Leave
Company Equipment
Parental Leave
Learning & Development Budget
Team Events & Social Budget
Paid Trial
Free Snacks & Drinks
Eligibility is set role by role: each posting's location label names the countries that role is open to. Fleetio has historically hired remotely across the United States, and many of its engineering and product roles have also been open to candidates in Canada and Mexico. Nothing on Fleetio's careers or engineering pages invites applications from Europe, Asia-Pacific or anywhere in the world, so treat the posting's label as the rule.
Fleetio publishes a four-stage process for engineering roles on its engineering careers page. It starts with a one-hour interview with the Lead Software Engineer and/or the hiring manager, followed by a small coding project that Fleetio pays you to complete. Next is a two-hour team interview with several engineers, which walks through your project and covers technical and team-fit questions. The last stage is a conversation with the CTO, followed by an offer. Fleetio has not published an equivalent process for non-engineering roles.
Two quarterly allowances stand out: a $150 wellbeing fund and a $125 business expense stipend, alongside a Mac laptop and a new-hire equipment stipend. Time off starts at four weeks of PTO, increasing at year two, plus 12 company holidays and 2 floating holidays. Health and dental coverage is 100% for the employee and 50% for family, and Fleetio also provides community service funds.
Fleetio does not publish a pay-transparency policy. No pay-transparency or pay-equity statement appears on its careers, culture or engineering pages, and salary ranges have not been a standard part of its job postings, so check the individual posting and ask about the range early. The one compensation element Fleetio describes as company-wide is equity: it grants all team members incentive stock options.
Fleetio does not publish them. Its careers, culture and engineering pages carry no core-hours, meeting, timezone-overlap or documentation-first policy, and there is no public employee handbook. The closest stated norm is the Work-Life Balance tenet of its engineering philosophy: focus intensely to get things done at work, then leave with enough satisfaction to focus on life. Ask each team how it handles meetings and time zones during your interviews.
Only one perk does. The fully stocked kitchen with drinks and snacks is marked "BHM only," and Fleetio lists no remote equivalent for it. None of Fleetio's other listed benefits, from the wellbeing fund to the equipment stipend, is tied to the office.
