Paralegal

PerkSpot • Chicago, IL

2d • Hybrid

About The Position

PerkSpot is searching for a Paralegal to join our Legal team! At PerkSpot, our mission goes beyond discounts—it’s about empowering employees everywhere to make smarter spending decisions so they can do more of what they love. We believe every dollar saved can become a stepping stone to a brighter future, whether that’s a special family vacation, a first home, or simply extra peace of mind.
We are seeking a detail-oriented and proactive Paralegal with strong contracting and legal operations experience to support our Legal and cross-functional business teams. This role will focus on reviewing, organizing, and managing a high volume of commercial agreements while ensuring compliance with company policies and applicable laws.
This position is required to be in the office 3 days a week on Tuesday, Wednesday, and Thursday. Our office is located in the Merchandise Mart in downtown Chicago, IL.

Requirements

• Bachelor’s degree or equivalent experience
• 3-5 years of paralegal experience with significant contract review and redlining experience.
• Strong knowledge of commercial contract structures and common legal terms.
• Experience working in-house or with corporate transactional matters.
• Exceptional attention to detail and organizational skills.
• Ability to manage multiple deadlines independently.

Nice To Haves

• Paralegal certificate preferred.
• Experience supporting a SaaS or technology company.
• Familiarity with Salesforce, Jira, and AI such as ChatGPT, Claude, Harvey, or GC.AI is strongly preferred
• Experience with data privacy or compliance documentation.
• Experience with cross-border matters in Canada, Mexico, and/or the UK.

Responsibilities

• Review and revise a variety of commercial agreements, including: NDAs, Vendor agreements, Customer agreements, SaaS agreements, Statements of Work (SOWs), Amendments and addenda
• Identify and escalate legal risks or non-standard terms to counsel.
• Ensure contracts align with internal policies and risk thresholds.
• Track contract status, key dates, renewals, and termination deadlines.
• Maintain accurate contract records and version control within Salesforce.
• Support audits and due diligence requests.
• Partner with Sales, Finance, HR, Procurement, and Operations teams to facilitate timely contract execution.
• Provide guidance on contract process and documentation requirements.
• Support process improvements and standardization efforts.
• Assist with corporate governance documentation and recordkeeping.
• Ensure compliance with regulatory and internal documentation requirements.
• Support legal research and special projects as needed.

Benefits

• Competitive salary
• matching 401K
• company paid disability
• Comprehensive medical, dental, and vision insurance is effective on your first day of employment!
• 20 days off each year
• 8 paid company holidays
• office is closed from Christmas Eve through New Year's Day
• Summer Fridays
• close at 1 pm the day prior to each company holiday as “holiday eve.”
• paid Sabbatical for up to 3 months to employees at 5 years and 10 years of service.
• monthly transportation stipend
• free lunch every Wednesday
• regular outings, virtual events, fun community-interest Slack channels, and occasional happy hours.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level