Contract Helpdesk Jobs in Chicago, IL (NOW HIRING)

Note to Candidates
We meticulously craft our job descriptions to clearly define the skills necessary for success and the expected performance level of the role, resulting in detailed content. Our goal is to ensure the description accurately reflects the job you will perform.
This is a hybrid role (three days per week at our HQ in Chicago, IL) and reports to the Director of Accounting.
Who We Are
Crafty elevates workplace food and beverage programs with enhanced services managed in one innovative, centralized platform. Founded in 2015, our mission is to help companies craft better workplaces. From DraftKings to Robinhood to Zillow, we work with the world's biggest brands to foster a culture of employee connectivity and productivity. Headquartered in Chicago, with offices in New York and the Bay Area, Crafty manages food and beverage programs across 300+ offices, serving more than 300,000 employees per month.
Our commitment to crafting better workplaces starts from within. We are a team of passionate, resourceful, and hard-working trailblazers who love what we do. Our expertise spans technology, food and beverage operations, client success, fulfillment, and more. At Crafty, our people are our greatest asset, because it's our people who foster a culture that makes our company a place worth being part of. And of course, the snacks are the cherry on top!
The Role
Crafty is seeking a Contract Specialist to add capacity and rigor to our contract operations. This is a primarily internal-facing role: you will process a high volume of contract requests, strengthen the systems that support our contract lifecycle, and train internal teams on request-processing mechanics. Client interaction is limited to redlining support - client relationships and account context stay with our field and commercial teams.
This role does not own client renewals or amendments end to end. Our account management teams own the client-facing workflow - this role exists to give them the systems, training, and processing capacity that make that ownership possible.
The Team
Crafty's contract team is a two-person team of individual contributors. Our Senior Contract Specialist is the subject matter expert for the contract lifecycle and owns contract language decisions, systems configuration, and the renewal calendar. This role adds bandwidth alongside that work, focused on execution volume, data integrity, and internal enablement.
The Senior Contract Specialist will coach you, help you onboard, and be your go-to resource for complex contract questions, but will not manage your work or approve your day-to-day output. You are expected to operate independently within Crafty's established negotiation guidelines, and to bring novel or high-risk contract language to the Senior Contract Specialist as an expert resource rather than as an approver.
Key Responsibilities

• Draft, review, and negotiate client and vendor contracts, ensuring clear terms and legal compliance using the company's contract negotiation guidelines. Collaborate with legal teams as needed to protect company interests, and provide redlining support to counterparties when required.
• Maintain an organized contract database, track key dates (renewals, deadlines), and ensure proper archiving. Ensure timely follow-up on expiring or active contracts to prevent lapses and maintain compliance with terms.
• Work closely with Client Success, Sales, and Finance teams to ensure smooth contract execution, aligning on terms, deliverables, and financial arrangements. Provide contract-related guidance to internal teams as needed.
• Send notifications related to contract renewal calendar.
• Update and standardize contract templates to ensure consistency, legal compliance, and efficiency. Collaborate with legal and relevant stakeholders to revise templates as needed to align with business or regulatory changes.
• Identify potential risks in contracts, such as financial or legal issues, and escalate them to senior management or legal teams. Ensure high-risk contracts are reviewed and adjusted as needed.
• Support regulatory and internal audits related to contracts.
• Process contract requests submitted across HubSpot and Ironclad, and help reduce duplicate data entry between the two systems as our integrations mature.
• Maintain and iterate the standard operating procedures for contract renewals and amendments, and deliver recurring training to internal request owners so they can move contracts forward independently.
• Support the post-signature process, including recording contract outcomes in our internal systems, coordinating with the equipment team on equipment-related changes, and looping in Implementation on office moves.

Required Attributes
Strong Understanding of Contract Terms and Commercial Implications: In-depth knowledge of contract terminology and the ability to assess and understand the commercial and legal implications of various contract clauses.
Effective Communication:

• Team Collaboration: You work well with others to achieve shared goals, providing and receiving constructive feedback to enhance team performance.
• Clear Communication: You effectively convey information and ideas clearly and concisely, fostering understanding and engagement.

Strong Multitasking and Time Management Skills: Ability to manage and prioritize multiple contracts simultaneously while maintaining high attention to detail and meeting deadlines in a fast-paced environment.
Exceptional Attention to Detail and Organizational Skills: Ability to consistently maintain a high level of accuracy in contract preparation, review, and management while keeping organized in a fast-paced environment.
Adaptability:

• Resourcefulness: You remain flexible and proactive as circumstances evolve, demonstrating a hardworking and resourceful approach.

Ideal Experience

• Bachelor's degree preferred
• 3+ years of experience in contract administration or legal operations
• Familiarity with contract lifecycle management tools (Ironclad), CRM platforms (HubSpot), and project management tools (Notion)
• Experience working with legal and compliance teams
• Experience training or enabling non-legal stakeholders on contract processes

Don't meet all of the qualifications? We want you to consider all of your skills and experiences - both professional and personal - that would make you successful in this role. Although some qualifications are essential, others can be attained with time. We believe diverse perspectives, upbringings, and knowledge contribute to our strong company culture and we encourage you to apply.
Role Goals

• Goal #1: Contract Processing Throughput: Be fully ramped and independently carrying a share of the contract request queue by the end of your first full quarter, sustaining service levels of 2 business days from full approval to contract share for Sales, Client Success, and Partner contracts and 3-5 business days for redline review - holding those levels through peak renewal periods without backlog, and implementing at least one process change by Q4 2026 that measurably reduces average turnaround time against your first-quarter baseline.
• Goal #2: Internal Enablement & Self-Service: By Q4 2026, publish and drive adoption of at least 2 SOPs or self-service resources for account management, Sales, Client Success, and Finance teams, deliver training to each primary owning team, and establish a repeatable onboarding path so new internal request owners can be trained without one-off support - measured by a reduction in contract-related inbound questions to the contract team versus your first-quarter baseline.
• Goal #3: Contract Data Integrity & Repository Management: By Q4 2026, ensure executed contracts are consistently organized, searchable, and accurately tracked in Ironclad, with 95%+ of new contracts tagged with required metadata, renewal, expiration, owner, and counterparty fields maintained for all active contracts, a monthly review of upcoming renewals and key dates with notifications issued on schedule and zero lapsed contracts, and historical records backfilled to the same metadata standard.
• Goal #4: Applied AI-Assisted Contract Review: By Q4 2026, consistently apply the Ironclad Jurist review workflow established by the Senior Contract Specialist across your full queue - using AI to identify risk areas, summarize key terms, and support first-pass review before escalation - working from the team's clause and risk playbook, contributing documented improvements to it based on patterns seen in live review, and reporting adoption, accuracy, and turnaround-time impact across Sales, Client Success, and Partner contracts.

What we offer:
Our people mean everything to us. When you join Crafty, you're joining a team of passionate, smart, and supportive people who work incredibly hard and have a good time along the way.
We are proud to offer a compensation package that includes our Crafty healthcare plan, covering primary health, dental, and vision plans, 401k, paid time off, equipment certification courses, and parental leave. And, of course, it also includes Crafty-grade snacks, beverages, and fun events!
Lastly, this role offers a special opportunity: to have a major hand in shaping the future of a young, flourishing company. Your creativity, ambition, and work will steer the direction of our successes.
Our compensation amount for this role is targeted at $67,000 - $79,000 per year in Chicago. Final offer amounts are determined by multiple factors including cost of living based on location, candidate experience and expertise, and may vary from the amounts listed above.
Crafty provides equal employment opportunities (EEO) to all employees and applicants for employment without discriminating against race, color, religion, sex, sexual orientation, national origin, age, disability or genetics.