Experienced Senior Counsel – Digital Products, Data Analytics & Intellectual Property Legal Strategist (Full-Time, Remote-Enabled)

About arenaflex

arenaflex is a forward-thinking, purpose-driven organization that has grown from humble beginnings into a recognized leader in its industry. Founded on the principles of innovation, integrity, and an unwavering commitment to the communities it serves, arenaflex has built a legacy of more than a century of meaningful impact. Today, arenaflex operates thousands of locations and digital touchpoints across the United States, serving millions of customers and patients each day.

At arenaflex, our mission is to create happier lives through better health, better technology, and better access to essential services. We are proud to be a neighborhood destination where customers, patients, and partners can find comprehensive solutions supported by cutting-edge digital platforms. Our integrated physical and digital ecosystems are designed to deliver exceptional products, services, and experiences to communities nationwide.

arenaflex’s digital products and data analytics divisions are at the heart of our transformation into a modern, technology-forward organization. As we continue to expand our digital footprint, we are seeking a seasoned legal professional to help guide, shape, and protect the innovations that define our future. This is an extraordinary opportunity to join a company that values both legacy and innovation, and where your legal expertise will directly influence products used by millions.

Position Overview

arenaflex is hiring a Senior Counsel, Digital Products, Data Analytics & Intellectual Property to provide expert legal guidance to senior leadership, product teams, and business units on a wide range of matters affecting our digital, data, and technology operations. This role is ideal for an experienced attorney with a strong background in technology transactions, intellectual property, privacy, and product counseling who thrives at the intersection of law, technology, and business strategy.

Reporting to senior legal leadership, you will serve as a trusted advisor on legal issues ranging from foundational to complex, including technology agreements, intellectual property strategy, data licensing, marketing law, security regulations, and general commercial matters. The ideal candidate is a quick learner, a strategic thinker, and a collaborative partner who can operate independently in a fast-paced, evolving environment.

Key Responsibilities

• Provide high-quality, practical legal counsel and recommendations to business leaders and the board on a wide spectrum of legal issues affecting digital product and data analytics operations.
• Demonstrate deep expertise in technology transactions, product counseling, intellectual property, marketing law, security and privacy regulations, and general commercial contracting.
• Act as a flexible generalist capable of rapidly learning new areas of law and providing end-to-end product guidance across multiple business lines.
• Draft, review, and negotiate a wide variety of business agreements in support of arenaflex’s Digital and Data Analytics/Insights organizations, including master services agreements, vendor agreements, data licensing agreements, integration agreements, and supply contracts.
• Collaborate closely with internal Digital Product and Data Analytics teams, as well as external partners, to support the design, deployment, and operation of technology used by customers and patients.
• Work cross-functionally with business, product, marketing, insurance, security, and technology stakeholders to bring digital products and services to market efficiently and compliantly.
• Develop a thorough understanding of arenaflex’s digital product and service offerings, technology infrastructure, security and data protection systems, policies, and standard business agreements to provide consistent legal support across the organization.
• Maintain a clear understanding of arenaflex’s business objectives, technology roadmap, and operational challenges in order to develop and execute intellectual property portfolio strategies that advance business goals, protect innovation investments, and minimize legal risk.
• Leverage deep knowledge of legal specialties to provide practical advice while continuously building expertise in the business context in which arenaflex operates.
• Review and prepare legal documents prior to board presentation to ensure accurate articulation of legal substance, risk, and recommendations.
• Partner with specialty units to achieve corporate objectives while mitigating unnecessary business risk.
• Conduct legal research, analyze precedents, engage and manage outside counsel, draft legal documents, gather relevant information from multiple sources, and provide work direction to other professionals and paraprofessional staff in developing solutions to complex issues.
• Stay current on legal and business trends that may impact the specialty units served, proactively advising stakeholders on emerging risks and opportunities.

Essential Qualifications

• Juris Doctorate (JD) from an accredited law school.
• A minimum of 5 years of post-bar attorney legal work experience in a combination of law firm and corporate settings.
• Active licensure to practice law in at least one U.S. state.
• Active Illinois bar membership, or active bar membership in good standing in at least one U.S. jurisdiction.
• Demonstrated experience with time management skills, including prioritizing, organizing, and managing multiple tasks with varying deadlines.
• At least 5 years of experience contributing to financial decision-making in a professional environment.
• At least 5 years of direct leadership, indirect leadership, and/or cross-functional team leadership experience.

Preferred Qualifications

• Proven ability to thrive in a fast-paced, evolving environment where prioritization and independent judgment are critical to success.
• Strong interpersonal and communication skills, with the ability to influence stakeholders at all levels of the organization.
• Experience working within retail, healthcare, pharmacy, or consumer-facing digital product organizations is a plus.

Skills and Competencies for Success

• Exceptional analytical, drafting, and negotiation skills.
• Strong business acumen paired with deep legal expertise.
• Ability to distill complex legal issues into clear, actionable guidance for non-legal stakeholders.
• Comfort navigating ambiguity and rapidly shifting priorities.
• High emotional intelligence and a collaborative, team-first mindset.
• Detail-oriented with a commitment to delivering high-quality work under tight deadlines.

Why Join arenaflex?

Joining arenaflex means becoming part of an organization that is reshaping the future of digital health and data-driven consumer experiences. We offer more than just a job — we offer a career path with purpose, impact, and opportunity.

Career Growth and Learning Opportunities

At arenaflex, you’ll work alongside some of the brightest minds in digital products, data analytics, and legal strategy. We invest in our people through mentorship programs, continuing legal education support, leadership development, and exposure to high-impact projects. Whether you aspire to deepen your expertise in technology law or expand into broader executive leadership, arenaflex provides the platform and resources to help you achieve your goals.

Work Environment and Culture

arenaflex fosters a culture of inclusion, collaboration, and innovation. We believe that diverse perspectives drive better outcomes, and we are committed to creating a workplace where every team member feels valued and empowered. Our hybrid and remote-enabled work model provides flexibility while maintaining strong team connection and engagement.

Compensation and Benefits

• Competitive hourly compensation ranging from $20 to $30 per hour, commensurate with experience.
• Annualized earning potential of approximately $70,000–$80,000 based on hours worked and performance.
• Comprehensive health, dental, and vision insurance options.
• Retirement savings plan with company match.
• Generous paid time off and holiday schedule.
• Professional development and continuing education support.
• Employee wellness programs and resources.

How to Apply

If you are a seasoned legal professional ready to make a meaningful impact at one of the most dynamic organizations in the industry, we encourage you to apply today. To be considered, please have the following documents ready:

• Updated resume detailing your legal experience and qualifications.
• Law school transcripts and bar admission documentation.
• Professional certifications or licenses, if applicable.
• Passport-size photograph and signature for application records.

Please review the official application instructions carefully, complete the application form, attach all required documents, and submit your application. We look forward to reviewing your qualifications and welcoming you to the arenaflex team.

Take the next step in your career — apply to arenaflex today and help shape the legal foundation of the future of digital products and data innovation.