Experienced Senior Counsel – Digital Products, Data Analytics & Intellectual Property

Full Job Description:

About arenaflex

Welcome to arenaflex, a leading integrated healthcare, pharmacy, and retail pioneer with a rich legacy dating back to 1901. Founded with a commitment to caring for communities, arenaflex has grown from a small neighborhood store on Chicago's South Side to become one of the nation's most trusted names in healthcare and retail pharmacy. Today, we operate nearly 9,000 retail stores across America, Puerto Rico, and the U.S. Virgin Islands, serving millions of customers and patients every single day. Our mission is simple yet profound: to create happier lives through better health.

At arenaflex, we believe that our people are our greatest asset. We take immense pride in our diverse team of pharmacists, healthcare professionals, technology innovators, and business strategists who work collaboratively to deliver an omnichannel experience that truly makes a difference in the communities we serve. Our commitment to equitable access to healthcare and our focus on innovation have made us a cornerstone of the American healthcare system.

As part of the arenaflex Digital Products and Data Analytics teams, you will have the opportunity to shape the future of healthcare technology while working alongside passionate professionals who are dedicated to transforming how patients and customers experience care. Join us and become part of a culture that values excellence, integrity, innovation, and community impact.

Position Overview

arenaflex is currently seeking a highly skilled and experienced Senior Counsel to join our Digital Products, Data Analytics, and Intellectual Property team. This is a pivotal role that offers the chance to provide strategic legal counsel to executive leadership and management across various specialized business units. You will be instrumental in navigating complex legal matters that directly impact our business activities and operations, particularly in the areas of technology transactions, product guidance, intellectual property, marketing, and security regulations.

This position requires a legal professional who thrives in a fast-paced, dynamic environment and possesses the ability to quickly master new areas of law and legal skills. You will serve as a trusted advisor, offering end-to-end product guidance while structuring and negotiating a wide variety of business agreements that support our Digital and Data Analytics organizations.

Key Responsibilities

As a Senior Counsel at arenaflex, you will be responsible for:

• Strategic Legal Advisory: Provide sound counsel and recommendations to operational leaders and management within various specialty units regarding matters of varying complexity (fundamental to transitional) that have or may affect business activities and operations.
• Technology Transactions Expertise: Demonstrate mastery in technology transactions, product guidance, intellectual property, marketing, security, and privacy laws. You must be prepared to act as a generalist and rapidly learn new areas of regulation and legal skills while providing comprehensive end-to-end product guidance.
• Business Agreement Negotiation: Structure and negotiate a wide range of business agreements on behalf of arenaflex's Digital and Data Analytics/Business Insights organizations, including master service agreements, supplier agreements, data licensing/integration, and supply agreements.
• Cross-Functional Collaboration: Partner with teams across arenaflex Digital Product and Data Analytics groups, as well as close external partners who are building, deploying, and operating technology for use by our customers and patients.
• Cross-Functional Partnership: Work cross-functionally with business, product, marketing, insurance, security, and technology teams to bring our digital product and service offerings to market successfully.
• Product and Technology Understanding: Develop and maintain a thorough understanding of arenaflex's digital product and service offerings, technology infrastructure, security/data protection systems and policies, and standard business and various contracts to provide a foundation for offering legal support throughout arenaflex Digital teams.
• Intellectual Property Strategy: Maintain awareness of arenaflex's business objectives, technology, and product goals and challenges to establish and execute intellectual property portfolio strategies that facilitate those goals, capture investments in innovation, and minimize legal risk, working closely with external counsel.
• Legal Documentation Review: Review and prepare legal documents before presentation to management for execution to ensure accurate articulation of the legal substance.
• Legal Research and Analysis: Research legal principles and precedents, engage with and manage outside counsel, draft legal documents, gather relevant case-related information using multiple sources and methods, and provide work direction to other professional, paraprofessional, and clerical staff in developing solutions to issues presented.
• Risk Mitigation: Collaborate with the specialty units you serve to achieve corporate objectives and mitigate unnecessary business risk while maintaining current knowledge of legal and business trends that could impact those specialty units.

Essential Qualifications

To be considered for this position, you must meet the following requirements:

• Education: Juris Doctorate (J.D.) from an accredited law school.
• Experience: Minimum of 5 years of post-bar attorney legal work experience in a combination of law firm and corporate settings.
• Bar Admission: Active licensure to practice law in at least one U.S. state. Illinois bar admission or active bar membership in at least one U.S. jurisdiction is required.
• Time Management: Strong time management skills, including the ability to prioritize/organize and track details while meeting deadlines for multiple tasks with varying completion dates.
• Financial Acumen: Minimum of 5 years of experience contributing to financial decisions in the workplace.
• Leadership Experience: Minimum of 5 years of direct leadership, indirect leadership, and/or cross-functional team leadership experience.

Preferred Qualifications

While not required, the following qualifications would strengthen your application:

• Experience working in a fast-paced environment where prioritization and the ability to work independently are essential for success.
• Background in healthcare, pharmacy, or retail technology law.
• Experience with data privacy and protection regulations, including HIPAA compliance.
• Knowledge of intellectual property portfolio management and strategy.
• Familiarity with technology licensing, SaaS agreements, and data analytics partnerships.

Skills and Competencies

Successful candidates will demonstrate:

• Exceptional analytical and problem-solving abilities.


• Excellent written and verbal communication skills.


• Strong organizational and multitasking capabilities.


• Business acumen with the ability to understand commercial objectives.


• Proactive approach to identifying legal risks and developing mitigation strategies.


• Ability to build relationships and collaborate effectively across departments.


• Sound judgment and the ability to provide practical, business-oriented legal advice.


• Adaptability and willingness to learn new areas of law quickly.

Career Growth and Development Opportunities

At arenaflex, we are committed to the professional development and growth of our team members. As a Senior Counsel in our Digital Products and Data Analytics division, you will have access to:

• Exposure to cutting-edge digital health technology and innovation initiatives.


• Opportunities to work on high-profile projects that shape the future of healthcare delivery.


• Mentorship from senior legal leaders and business executives.


• Continuing education opportunities in emerging areas of law, including data privacy, artificial intelligence, and digital health regulations.


• Career advancement potential within our Legal Department and across the broader organization.


• Networking opportunities with external partners, including technology vendors, startups, and industry associations.

Work Environment and Culture

arenaflex fosters a collaborative, inclusive, and innovative work environment where diverse perspectives are valued and celebrated. Our Legal team is known for its collegial atmosphere, commitment to excellence, and focus on delivering practical legal solutions that support business objectives.

We offer:

• Flexible work arrangements, including remote and hybrid options.


• Comprehensive onboarding and training programs.


• Access to state-of-the-art technology and resources.


• A supportive team culture that encourages open communication and idea-sharing.


• Exposure to a wide range of legal matters across multiple business units.

Compensation and Benefits

arenaflex offers a competitive compensation package that includes:

• Base salary range: $20-$30 per hour (commensurate with experience and qualifications).


• Annual performance bonuses.


• Comprehensive health, dental, and vision insurance.


• 401(k) retirement plan with company match.


• Paid time off and holidays.


• Employee assistance program.


• Professional development reimbursement.


• Various employee discounts and perks.

How to Apply

If you are a motivated legal professional seeking a challenging and rewarding opportunity to make a significant impact at a leading healthcare and retail company, we encourage you to apply.

To be considered, please submit your application through our official careers portal. Ensure you have the following documents ready:

• Resume/Curriculum Vitae


• Cover letter highlighting your relevant experience and qualifications


• Law school transcript


• Bar admission documentation


• List of references

arenaflex is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.

Join Our Team

This is an exceptional opportunity to join a world-class organization and contribute to our mission of creating happier lives through better health. If you are ready to take the next step in your legal career and make a meaningful impact in the healthcare industry, we invite you to apply today.

Come be part of something bigger. Come grow with arenaflex.