Senior Corporate Paralegal, Fleetio
Salary not provided
+Stock options
Salesforce
JIRA
Docusign
Google Workspace
Senior and Expert level
Remote from Canada, US
Fleet management software
Posted today
Fleet management software
201-500 employees
B2BTransportNavigationSaaSMobile
Posted today
Salary not provided
+Stock options
Salesforce
JIRA
Docusign
Google Workspace
Senior and Expert level
Remote from Canada, US
201-500 employees
B2BTransportNavigationSaaSMobile
Company mission
To help organizations track, analyze and improve their fleet operations.
Role
Who you are
- 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
- 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
- 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
What the job involves
- 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
- 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
- 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
Our take
Fleetio offers software that helps organizations track, analyze, and improve their fleet operations. Fleet management is a famously complex and challenging task, so Fleetio's services unburden organizations of this, enabling them to focus time and energy on their own mission.
The company makes it easier for businesses to lease a fleet of vehicles with an app which allows managers, drivers and mechanics to access and update information, relieving users of outdated fleet software and complicated spreadsheets. This simple solution has proven effective with the start-up seeing nearly 400% growth in a three-year margin.
The company had a successful 2025 too, having raised over $450M early in the year, which also included the acquisition of Auto Integrate. With moves like this, Fleetio can certainly expect to continue its growth, especially given its stable position in a market estimated to be worth $52.4 billion by 2027.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
Top investors
18% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2025
$450m
SERIES D
May 2023
$144.7m
SERIES C
Total funding: $620m
Company benefits
- Health & Wellness: Taking care of you and your family is important to us. Our healthcare plans deliver choice and value so you can prioritize your health
- 401k Match: Plan for your future. We match your retirement contributions up to 4% of your salary each pay period
- PTO/Holidays: Four weeks of paid time off (PTO), two floating holidays, as well as 12 company holidays
- Parental Leave: We provide all our team members (birthing & non-birthday parents) time off to care for and bond with their newborn or newly adopted children
- Stock Options: At Fleetio, we grant all our team members options to acquire an ownership stake in Fleetio
- Professional Development: Team members get an annual professional development allowance to invest in their own professional growth
Company HQ
Central City, Birmingham, AL
Leadership
Jon Meachin
(CEO)Jon initially joined Fleetio as COO in 2022, becoming CEO in 2023. Prior to this, they were COO at A Cloud Guru and held VP roles at Campaign Monitor and McKissock.
Matthew Mandel
(CFO & COO)Prior to joining Fleetio in 2023, Matthew was the COO & Co-CEO at Cometeer. They also spent 3 years at Wayfair in various General Manager roles.
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