Head of Legal & Compliance

AKIRA•Chicago, IL

13d•Onsite

About The Position

AKIRA is seeking a commercially driven, execution-focused Head of Legal & Compliance to build and lead the company's internal legal function. This is a high-velocity, player-coach role for a business-minded attorney who can independently negotiate complex commercial agreements, aggressively manage outside litigation counsel, and proactively protect a fast-moving national retail brand. The role will directly support: 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 successful candidate must be decisive, pragmatic, and comfortable operating at "fashion speed" - delivering real-time risk analysis while enabling growth. This position is hands-on. It is not a pure oversight role. The attorney must personally draft, redline, negotiate, and drive matters to resolution.

Requirements

Juris Doctor (J.D.)
Active Illinois Bar License (in good standing)
5–9 years of legal practice.
Combination of: Commercial transactions (retail leasing and SaaS strongly preferred), Litigation management (insurance-backed defense experience required)
Proven ability to independently redline: Retail leases, Complex SaaS agreements
Comfortable managing multiple live disputes simultaneously.
Pragmatic decision-maker.
Understands risk vs reward.
Can provide clear, executive-level summaries.
Moves quickly without sacrificing precision.

Nice To Haves

Prior in-house retail or technology company experience strongly preferred.
Comfortable in an entrepreneurial, founder-driven culture.
High accountability and ownership mindset.
Comfortable challenging insurance carriers and outside counsel.
Not bureaucratic.
Executes decisively.
Understands both brick-and-mortar retail and digital risk.

Responsibilities

Draft, review, and negotiate commercial retail leases, renewals, amendments, subleases, and guaranties.
Partner with the Real Estate team on new market entry strategy and site risk assessment.
Analyze and negotiate co-tenancy clauses, kick-outs, exclusives, CAM language, and landlord work letters.
Lead lease abstract review and risk mitigation planning.
Manage landlord disputes, default notices, CAM audits, and rent reconciliation matters.
Coordinate outside real estate counsel when required.
Provide risk analysis for store closures, relocations, and early terminations.
Review and negotiate construction contracts, contractor agreements, maintenance vendors, and logistics providers.
Ensure indemnification, insurance, and limitation-of-liability protections are properly structured.
Lead legal review and negotiation of: SaaS agreements, Enterprise licenses, Technology integrations, IT managed service contracts
Negotiate: Data security provisions, Service level agreements (SLAs), Uptime guarantees, Liability caps, Indemnification protections
Partner with IT leadership to balance risk vs operational speed.
Ensure contracts adequately protect AKIRA's: Customer data, Payment systems, E-commerce uptime, Marketing platforms
Review vendor security posture and privacy terms.
Manage trademark portfolio (filings, renewals, enforcement).
Oversee brand protection matters in fast-fashion enforcement scenarios.
Coordinate outside IP counsel on infringement disputes.
Direct outside counsel on: TCPA class actions, ADA website accessibility claims, Consumer protection disputes, Contract disputes, Employment claims
Evaluate exposure and provide executive-level risk assessments.
Develop litigation strategy aligned with cost control and brand protection.
Act as primary liaison with carriers (CNA, Travelers, EMC).
Manage tenders and challenge coverage denials.
Review and negotiate policy renewals with brokers.
Optimize coverage positioning and recovery strategy.
Lead settlement strategy discussions.
Participate in mediations.
Drive cost-effective closure of active matters.
Advise HR and executive leadership on: Wage & hour compliance, Termination strategy, Multi-state employment issues, Discrimination and retaliation risk mitigation
Review employment agreements and policy updates.
Provide guardrails for: SMS marketing, Email marketing, Consumer data usage
Ensure compliance with: TCPA, CCPA, CAN-SPAM, Emerging state privacy regulations