Senior Contracts Specialist

Cart.com•Time, IL

1d•Hybrid

About The Position

As a Senior Contract Specialist, you will serve as a strategic partner across Cart.com’s business, owning complex commercial contracting activities and elevating our contract operations across the company. Reporting to the Sr. Director of Contracts, you will lead high-impact negotiations, manage complex customer and vendor agreements, and act as a subject-matter expert for internal teams. You will mentor junior team members, drive improvements to our contract lifecycle processes, and collaborate directly with senior leaders, the General Counsel, Sales, Finance, Operations, Procurement, Product, and other cross-functional teams. This role is ideal for someone who thrives in a fast-paced, high-growth environment, brings deep contracting expertise, and is ready to step into a broader leadership-oriented position while still being hands-on.

Requirements

8+ years of professional experience drafting, reviewing, and negotiating commercial contracts.
In-house experience with Legal, Procurement, or Commercial Contracts teams.
Significant experience leading complex negotiations with enterprise customers or vendors, ideally in SaaS, ecommerce, logistics, or technology environments.
Proven track record managing multiple concurrent high-impact contracts while maintaining accuracy and meeting tight deadlines.
Experience advising cross-functional teams and providing structured risk assessments or contract recommendations.
Experience improving contracting processes, implementing templates, or supporting CLM systems.
Experience managing or mentoring junior contracting staff (formal or informal leadership).
Experience handling confidential information with discretion and professionalism.

Nice To Haves

Experience with SaaS, ecommerce, or supply chain/logistics agreements.
Experience using and managing contract lifecycle management (CLM) tools.
Background developing contract playbooks, clause libraries, or negotiation frameworks.
Experience working for a small business in a contract, procurement, or legal capacity.

Responsibilities

Contract Strategy & Execution Lead the review, drafting, redlining, and negotiation of complex commercial agreements including MSAs, SOWs, SaaS agreements, logistics/fulfillment agreements, data processing agreements, amendments, and NDAs.
Serve as the escalation point for non-standard, high-risk, or complex contract terms with material business impact.
Independently develop negotiation strategy and guide internal stakeholders on risk, alternative language, and best practices for contract structures.
Cross-Functional Leadership Act as a trusted advisor to senior executives and department leaders, providing guidance on contractual risk, compliance requirements, and deal structures.
Proactively partner with Sales, Legal, Procurement, Operations, and Finance to align contract execution with business goals and customer needs.
Mentor, coach, and support Contract Specialists on best practices, draft reviews, and negotiation preparation.
Process Improvement & Systems Ownership Drive enhancements to the contract lifecycle management (CLM) process, tools, templates, and forms.
Lead initiatives to streamline workflows, reduce contract cycle time, and improve internal compliance.
Support implementation, optimization, and administration of contract management systems.
Risk Management & Governance Ensure contract terms comply with Cart.com policies, legal requirements, data privacy standards, and customer obligations.
Identify risk issues early, develop mitigation strategies, and collaborate with the General Counsel on complex matters.
Own accuracy and completeness of contract records, reporting, version control, audit readiness, and system-based documentation.