Head of Legal & Compliance

AKIRA Head of Legal & Compliance

In 2002, AKIRA opened the doors to its first women's clothing boutique in Chicago. Since then, the company has extended its reach to 40+ stores across the United States, as well as a thriving eCommerce business (shopAKIRA.com). AKIRA is extremely well-poised for sustained growth as we continue to build a nationally recognized brand. AKIRA's culture has one very large, distinct difference from other high fashion competitors: Other-Worldly Customer Service and Fanatical, Obsessive Attention to the consumer's needs and desires. The core principle for all employees at AKIRA is to Act and Think Like an Owner, and this belief can be reflected across all areas of the company.

The Position: Head of Legal & Compliance

Location: Chicago, IL- Full-time Onsite

Position Summary:

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.

Core Responsibilities:

Retail Real Estate & Expansion Strategy

• 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.

Portfolio Risk Management

• 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.

Portfolio Risk Management

• 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.

Facilities & Vendor Agreements

• Review and negotiate construction contracts, contractor agreements, maintenance vendors, and logistics providers.
• Ensure indemnification, insurance, and limitation-of-liability protections are properly structured.

Technology, SaaS & Intellectual Property

SaaS & IT Procurement

• 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.

E-Commerce & Data Compliance

• Ensure contracts adequately protect AKIRA's:
  • Customer data
  • Payment systems
  • E-commerce uptime
  • Marketing platforms
• Review vendor security posture and privacy terms.

Intellectual Property Protection

• Manage trademark portfolio (filings, renewals, enforcement).
• Oversee brand protection matters in fast-fashion enforcement scenarios.
• Coordinate outside IP counsel on infringement disputes.
  
  

Litigation Management & Insurance Strategy

AKIRA maintains active federal and state litigation matters typical of large retail and digital brands.

Strategic Litigation Oversight

• 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.

Insurance Recovery & Coverage Advocacy

• 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.

Resolution & Settlement

• Lead settlement strategy discussions.
• Participate in mediations.
• Drive cost-effective closure of active matters.
  
  

Employment Law & Marketing Compliance

Employment Risk Advisory

• 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.

Marketing & Privacy Compliance

• Provide guardrails for:
  • SMS marketing
  • Email marketing
  • Consumer data usage
• Ensure compliance with:
  • TCPA
  • CCPA
  • CAN-SPAM
  • Emerging state privacy regulations
    

STRATEGIC EXPECTATIONS

Within 12 months, this role should:

• Reduce outside counsel spend through improved matter management.
• Standardize contract templates and playbooks.
• Improve lease negotiation efficiency.
• Strengthen insurance recovery outcomes.
• Implement a risk-prioritization framework for leadership.
• Establish a centralized legal tracking system for active matters.
  
  

REQUIRED QUALIFICATIONS

Education

• Juris Doctor (J.D.)
• Active Illinois Bar License (in good standing)

Experience

• 5–9 years of legal practice.
• Combination of:
  • Commercial transactions (retail leasing and SaaS strongly preferred)
  • Litigation management (insurance-backed defense experience required)
• Prior in-house retail or technology company experience strongly preferred.

Technical Capability

• Proven ability to independently redline:
  • Retail leases
  • Complex SaaS agreements
• Comfortable managing multiple live disputes simultaneously.

Business Orientation

• Pragmatic decision-maker.
• Understands risk vs reward.
• Can provide clear, executive-level summaries.
• Moves quickly without sacrificing precision.
  
  

IDEAL CANDIDATE PROFILE

• 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.
  
  

TEAM STRUCTURE

• Direct report to COO.
• Will manage outside counsel across:
  • Real estate
  • Litigation
  • IP
  • Employment
• No direct reports initially; opportunity to build legal team over time.

Benefits and Perks:
AKIRA offers competitive benefits for full-time employees, including Medical, Dental, Vision, Pet Insurance, Life, LTD, FSA/HSA/Dependent Care FSA, Flex Transit (CTA), 401(k), and a generous employee discount. We're committed to internal growth, providing meaningful development and career advancement opportunities.

Compensation:
At AKIRA, we are committed to fair and transparent compensation practices. Compensation for this position will be determined based on experience, qualifications, and other job-related factors. Additional compensation and benefits may also apply and will be discussed during the hiring process. Job Type: Full-Time

Salary

• $165,000 - $180,000/per base