Paralegal

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.

What you’ll accomplish:

Contract Management

• 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.

Cross-Functional Collaboration

• 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.

Compliance & Governance

• Assist with corporate governance documentation and recordkeeping.
• Ensure compliance with regulatory and internal documentation requirements.
• Support legal research and special projects as needed.

What we’re looking for:

• Bachelor’s degree or equivalent experience
• Paralegal certificate preferred.
• 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.

Preferred Skills & Qualifications:

• 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.

Skills & Competencies

• Strong written and verbal communication skills
• Sound judgment and ability to identify legal risk
• Process-oriented with a continuous improvement mindset
• High level of discretion and professionalism
• Ability to work collaboratively across departments

About PerkSpot:

At PerkSpot, we believe that life is about getting the most out of every dollar, every moment, and every opportunity. We don’t just see a discount; we see a doorway to craft a lifestyle that balances smart choices with meaningful experiences. We celebrate the relentless pursuit of value, the satisfaction of finding that perfect deal, and the sense of confidence that comes from spending with intention. Every dollar saved is a step closer to the life you envision—one that’s rich in memories, secure in planning, and full of everyday wins that bring joy and fulfillment.

Our journey began in Chicago back in 2006 with a vision of helping employees stretch their paychecks without sacrificing what they love. What began as a small company with a big vision has evolved into a discount shopping solution employees across the globe rely on to stretch their paychecks. In 2018, PerkSpot raised $50M from Susquehanna Growth Equity and today the business serves more than 22 million employees from top employers including Southwest Airlines, Mayo Clinic, and Humana. We saw an opportunity to do more—to build something that brought genuine, life-enhancing value to employees’ everyday financial decisions.

Your first few months as a PerkSpotter:

Providing value doesn’t have to wait, from day one we are open to your big ideas. In your first few months, you will:

• Meet the team! We think our people are pretty great so we want to ensure you’re introduced to all of the right team members to help you succeed. You’ll report to the General Counsel and spend quite a bit of time with our Sales teams.
• Get to know PerkSpot! Immerse yourself in the business, engage with internal stakeholders, and participate in monthly company-wide All Hands meetings.
• Sharpen your skills! You will become very familiar with our contracting procedures and ensure compliance with company policies and applicable laws.
• See your impact! You’ll build strong relationships with our internal business teams and own the contract management process.
• Participate in company-wide events ! Whether it’s office miniature golf or a raffle gameshow, company culture is at the forefront of our business.

The pay:

PerkSpot offers competitive industry rate salaries with the goal of retaining and growing talented individuals. We regularly review and adjust our compensation structure as needed to ensure equity and across teams and levels. The base salary range for this position is $90,000 - $110,000 plus $2k annual bonus.

The perks and benefits:

• Competitive salary, matching 401K, and company paid disability.

• Comprehensive medical, dental, and vision insurance is effective on your first day of employment!
• Time off is required. We want our team members to rest, relax, and recharge, so we encourage employees to take 20 days off each year.  Plus, we offer 8 paid company holidays and our office is closed from Christmas Eve through New Year's Day.
• Summer Fridays are great and are an annual tradition between Memorial Day and Labor Day every year.
• To help you get a jump start on company holidays, we close at 1 pm the day prior to each company holiday as “holiday eve.”
• Tenure is valued and rewarded. In addition to PTO, we offer a paid Sabbatical for up to 3 months to employees at 5 years and 10 years of service.
• Commuting can be expensive – we get it.  So, we provide a monthly transportation stipend and free lunch every Wednesday. 
• Connection and relationship building is everything. We offer regular outings, virtual events, fun community-interest Slack channels, and occasional happy hours.

How to apply:

All applications will be kept strictly confidential. Please submit a resume and cover letter telling us how you stack up to the qualifications, plus any other information you feel would be relevant to PerkSpot. Don’t be afraid to show your spark and personality!

All positions require a full background screening.

PerkSpot is an equal opportunity employer. Offering a diverse, equitable, and inclusive work environment is a priority at PerkSpot. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, or national origin, disability or protected veteran status, or any other legally protected basis, in accordance with applicable law.