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 portfolio
• A high‑volume digital marketing and e‑commerce engine
• A multi‑state workforce
• A rapidly evolving technology stack

The 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 Responsibilities

Retail Real Estate & Expansion

• Draft, 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 Management

• Manage 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 Agreements

• Negotiate construction contracts, contractor agreements, maintenance providers, and logistics vendors.
• Ensure proper indemnification, insurance, and liability protections.

Technology, SaaS & IP

SaaS & Technology Procurement

• Lead 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 Compliance

• Protect customer data, payment systems, e‑commerce uptime, and marketing platforms.
• Review vendor security posture, privacy obligations, and data‑handling practices.

Intellectual Property

• Manage trademark filings, renewals, and enforcement.
• Oversee brand‑protection efforts and coordinate outside IP counsel.

Litigation & Insurance Management

• Direct 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.

Insurance

• Serve as primary contact for insurance carriers.
• Manage tendering, challenge denials, and negotiate policy renewals.
• Optimize coverage and recovery strategies.

Employment & Marketing Compliance

• Advise 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.

Experience

• 5–9 years of legal practice
• Background in commercial transactions (retail leasing and SaaS strongly preferred)
• Litigation management experience, including insurance‑backed defense
• Prior in‑house retail or technology experience preferred

Business Orientation

• Pragmatic, commercially minded decision‑maker
• Provides clear, concise executive summaries
• Operates with urgency without sacrificing precision

Ideal Candidate Profile

• Thrives in a fast‑paced, founder‑driven environment
• High ownership and accountability
• Comfortable pushing back on carriers and outside counsel
• Not bureaucratic; decisive and execution‑focused
• Understands both brick‑and‑mortar retail and digital/e‑commerce risk

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