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Senior Legal Counsel – Digital Products & Data Analytics (Remote, Work‑From‑Home) – Compliance, Privacy & Technology Leadership

Remote, USA Full-time Posted 2026-06-12
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About arenaflex

arenaflex is a pioneering leader in the retail pharmacy and health‑services sector, operating a nationwide network of more than 9,000 stores and a robust digital platform that serves millions of customers daily. Founded over a century ago, arenaflex has continuously evolved, embracing cutting‑edge technology, data‑driven insights, and a customer‑centric approach to deliver seamless omnichannel experiences. Our mission is to improve lives through better health, and we achieve this by blending physical locations with innovative digital services, advanced analytics, and a commitment to equitable access to care.

Position Overview

arenaflex is seeking a highly skilled and strategic Senior Legal Counsel to join our Digital Products & Data Analytics team. This remote, work‑from‑home role will serve as a trusted advisor on complex legal matters that intersect technology, data privacy, product development, and regulatory compliance. You will partner with cross‑functional leaders—including product managers, engineers, data scientists, security, and marketing—to shape the legal framework that enables safe, innovative, and compliant digital solutions for our customers.

Key Responsibilities

  • Provide proactive, business‑focused legal counsel on a broad range of issues, including data privacy, cybersecurity, product liability, intellectual property, and regulatory compliance across multiple jurisdictions.
  • Lead the development, negotiation, and execution of technology contracts, vendor agreements, data licensing arrangements, and service‑level agreements that support arenaflex’s digital initiatives.
  • Collaborate closely with the Digital Product and Data Analytics teams to embed legal risk assessments early in the product lifecycle, ensuring that compliance considerations are integrated into design, development, and launch phases.
  • Draft, review, and maintain internal policies, standard operating procedures, and best‑practice guidelines related to data handling, privacy, security, and emerging technologies such as AI/ML and cloud services.
  • Act as the primary liaison with external counsel, managing relationships, overseeing deliverables, and ensuring alignment with arenaflex’s strategic objectives and risk tolerance.
  • Monitor and interpret evolving legislation, regulations, and industry standards (e.g., GDPR, CCPA, HIPAA, state privacy laws) and translate these requirements into actionable recommendations for business units.
  • Conduct internal investigations, respond to regulatory inquiries, and support litigation matters that arise from digital product offerings or data‑related disputes.
  • Provide training and education to internal stakeholders on legal implications of emerging technologies, data protection obligations, and compliance best practices.
  • Contribute to the development of arenaflex’s enterprise‑wide technology risk management framework, helping to balance innovation speed with legal safeguards.
  • Maintain a deep understanding of arenaflex’s business goals, technology roadmap, and market dynamics to anticipate legal challenges and propose forward‑looking solutions.

Essential Qualifications

  • Juris Doctor (JD) from an accredited law school and active admission to the bar in at least one U.S. jurisdiction (Illinois bar membership preferred).
  • Minimum of 5 years of post‑bar experience providing legal counsel in corporate environments, with a focus on technology, data privacy, and regulatory compliance.
  • Demonstrated expertise in drafting and negotiating complex technology contracts, data sharing agreements, and vendor arrangements.
  • Strong analytical skills with the ability to synthesize large volumes of legal and technical information into clear, actionable guidance.
  • Proven track record of working effectively in fast‑paced, cross‑functional teams and influencing senior leadership without direct authority.
  • Exceptional written and verbal communication skills, capable of translating legal concepts for non‑legal audiences.
  • Experience managing external counsel and coordinating multi‑jurisdictional legal projects.
  • Ability to prioritize competing demands, meet tight deadlines, and maintain high quality under pressure.

Preferred Qualifications

  • Additional certifications or coursework in data privacy (e.g., CIPP/US, CIPP/E), cybersecurity, or technology law.
  • Experience with health‑care regulations such as HIPAA, HITECH, or state‑specific health data statutes.
  • Background in product development or digital transformation initiatives within a large retail or consumer‑focused organization.
  • Familiarity with emerging technologies such as artificial intelligence, machine learning, blockchain, and cloud computing, and their associated legal considerations.
  • Demonstrated ability to lead or contribute to enterprise‑wide compliance programs or privacy impact assessments.

Core Skills & Competencies

  • Strategic Thinking: Ability to align legal advice with business objectives and long‑term product strategy.
  • Collaboration: Strong interpersonal skills to build relationships across product, engineering, data science, security, and marketing teams.
  • Risk Management: Proactive identification and mitigation of legal and regulatory risks.
  • Negotiation: Skilled in negotiating favorable terms while preserving strong partnerships with vendors and service providers.
  • Adaptability: Comfortable navigating a rapidly changing regulatory landscape and evolving technology stack.
  • Project Management: Ability to manage multiple, concurrent legal projects with clear timelines and deliverables.
  • Ethical Judgment: Commitment to upholding the highest standards of integrity and confidentiality.

Career Growth & Learning Opportunities

arenaflex invests heavily in the professional development of its legal talent. As a Senior Counsel, you will have access to:

  • Mentorship from senior executives and seasoned attorneys within the global legal organization.
  • Continuous learning programs, including certifications in privacy, cybersecurity, and emerging technology law.
  • Opportunities to lead high‑visibility projects that shape the future of digital health services.
  • Cross‑functional rotations that broaden your expertise across product, data analytics, and compliance functions.
  • Participation in industry conferences, webinars, and thought‑leadership forums to stay at the forefront of legal innovation.

Work Environment & Culture at arenaflex

Our remote‑first culture empowers employees to work from anywhere while staying deeply connected to the mission. arenaflex fosters an inclusive, collaborative environment where diverse perspectives are celebrated. Key cultural pillars include:

  • Innovation with Purpose: We encourage bold ideas that improve health outcomes and enhance customer experiences.
  • Integrity & Trust: Ethical conduct and transparency are non‑negotiable in everything we do.
  • Employee Well‑Being: Comprehensive wellness programs, flexible schedules, and mental‑health resources support a healthy work‑life balance.
  • Community Impact: arenaflex is committed to social responsibility, offering volunteer opportunities and community outreach initiatives.
  • Continuous Feedback: Regular performance conversations and peer recognition ensure growth and satisfaction.

Compensation, Benefits & Perks

arenaflex offers a competitive total rewards package that reflects the importance of this role, including:

  • Base salary range of $35,000 – $40,000 per year (adjusted for experience and location).
  • Performance‑based bonuses tied to individual and company success.
  • Comprehensive health, dental, and vision insurance plans.
  • Retirement savings options with company matching contributions.
  • Generous paid time off, holidays, and parental leave.
  • Remote‑work stipend covering home office setup, internet, and ergonomic equipment.
  • Professional development budget for certifications, courses, and conferences.
  • Employee assistance programs, wellness apps, and mental‑health resources.

Application Process

To be considered for this exciting opportunity, please follow these steps:

  1. Review the official job posting on the arenaflex careers portal.
  2. Prepare the required documents: a copy of your JD degree, bar admission certificate, official transcripts, and a recent passport‑size photograph.
  3. Complete the online application form, attaching your resume, cover letter, and the required documents.
  4. Submit the application and await a confirmation email with next steps.
  5. If selected, you will participate in a multi‑stage interview process, including a technical legal interview, a case study exercise, and a cultural fit discussion.

Why Join arenaflex?

At arenaflex, you will be at the nexus of law, technology, and health‑care, shaping products that directly impact the well‑being of millions. You will work alongside visionary leaders, cutting‑edge technologists, and passionate advocates for better health. If you thrive in a dynamic, remote environment and are eager to drive compliance while fostering innovation, arenaflex offers the platform to accelerate your career and make a meaningful difference.

Ready to Make an Impact?

If you are a strategic, detail‑oriented legal professional with a passion for digital products and data analytics, we invite you to apply today. Join arenaflex and help us build a safer, smarter, and more compassionate digital health ecosystem.

Apply Now

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