Head of Legal

Our client, a Chicago-based nationwide retailer + e-commerce business, is seeking a commercially minded, execution‑driven Head of Legal to build and lead the company’s first in‑house legal function. This is a high‑velocity, player‑coach role for an attorney who can independently negotiate complex commercial agreements, manage outside litigation counsel, and proactively safeguard a fast‑moving national retail brand. The role provides direct legal support for:A national retail real estate portfolioA high‑volume digital marketing and e‑commerce engineA multi‑state workforceA rapidly evolving technology stackThe ideal candidate is decisive, pragmatic, and comfortable operating at “fashion speed,” providing real‑time, business‑aligned risk assessments while enabling growth. This is a hands‑on role—fully responsible for drafting, redlining, negotiating, and driving matters to completion.Core ResponsibilitiesRetail Real Estate & ExpansionDraft, review, and negotiate retail leases, renewals, amendments, subleases, and guaranties.Partner with Real Estate leadership on market entry strategy and site‑level risk evaluation.Analyze co‑tenancy, exclusivity, kick‑outs, CAM provisions, and landlord work letters.Lead lease abstracting, compliance, and portfolio risk mitigation planning.Portfolio Risk ManagementManage landlord disputes, default notices, CAM audits, and rent reconciliation issues.Coordinate outside real estate counsel as needed.Provide legal guidance on store closures, relocations, and early terminations.Facilities, Construction & Vendor AgreementsNegotiate construction contracts, contractor agreements, maintenance providers, and logistics vendors.Ensure proper indemnification, insurance, and liability protections.Technology, SaaS & IPSaaS & Technology ProcurementLead negotiation of SaaS agreements, enterprise licenses, integrations, and managed services.Negotiate data security terms, SLAs, uptime guarantees, liability caps, and indemnities.Partner with IT to balance operational speed with effective risk control.E‑Commerce & Data ComplianceProtect customer data, payment systems, e‑commerce uptime, and marketing platforms.Review vendor security posture, privacy obligations, and data‑handling practices.Intellectual PropertyManage trademark filings, renewals, and enforcement.Oversee brand‑protection efforts and coordinate outside IP counsel.Litigation & Insurance ManagementDirect outside counsel across active litigation (TCPA, ADA web accessibility, consumer, contract, employment, etc.).Assess exposure and provide executive‑level risk summaries.Lead settlement strategy and participate in mediations.InsuranceServe as primary contact for insurance carriers.Manage tendering, challenge denials, and negotiate policy renewals.Optimize coverage and recovery strategies.Employment & Marketing ComplianceAdvise on wage/hour issues, terminations, discrimination risk, multi‑state compliance, and policy updates.Provide guidance for SMS/email marketing, data usage, and privacy compliance (TCPA, CCPA, CAN‑SPAM, emerging state laws).Strategic Expectations Reduce outside counsel spend through improved matter and vendor management.Standardize contract templates and negotiation playbooks.Improve lease negotiation efficiency and response speed.Strengthen insurance recovery outcomes.Implement a risk‑prioritization and reporting framework.Establish centralized tracking for contracts, disputes, and litigation.Experience5–9 years of legal practiceBackground in commercial transactions (retail leasing and SaaS strongly preferred)Litigation management experience, including insurance‑backed defensePrior in‑house retail or technology experience preferredBusiness OrientationPragmatic, commercially minded decision‑makerProvides clear, concise executive summariesOperates with urgency without sacrificing precisionIdeal Candidate ProfileThrives in a fast‑paced, founder‑driven environmentHigh ownership and accountabilityComfortable pushing back on carriers and outside counselNot bureaucratic; decisive and execution‑focusedUnderstands both brick‑and‑mortar retail and digital/e‑commerce riskOur specialized recruiting professionals apply their expertise and utilize our proprietary AI to find you great job and candidate matches faster.