Assistant General Counsel, Technology Transactions & Product (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life-changing impact that enriches lives and helps build a better future. Learn more at inspirafinancial.com.
We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday). This requirement does not apply to support specialist positions.
Don't meet every single requirement? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey. We look forward to receiving your application.
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The Assistant General Counsel will report to the Associate General Counsel in the Legal Department. The position will provide legal advice and guidance on a wide variety of commercial, contractual, and regulatory legal matters, with a focus on technology transactions and consumer-directed benefit solutions. The ideal incumbent will provide legal advice on a wide variety of specialized areas of law, including but not limited to: ERISA, IRS and DOL regulations, federal healthcare laws, privacy and intellectual property.

• Structure, draft and negotiate contracts for commercial technology transactions, including (i) SaaS agreements, (ii) API, licensing and subscription agreements, (iii) business development, co-development/co-marketing, and other strategic alliance arrangements, (iv) content, data, software procurement (via inbound licenses or purchases) and other types of inbound licensing and purchase agreements with third party providers, (v) data protection agreements, and (vi) end-user agreement terms.
• Work with business clients on contractual and regulatory exposures and risks related to the development of new customer offerings or services and related customer agreement terms, and existing enterprise and individual sales activities.
• Provide legal counsel on various corporate, regulatory compliance and intellectual property matters impacting Inspira, including legal trends and issues related to HIPAA compliance, privacy and consumer protection laws, and general federal and state healthcare regulatory schemes.
• Provide legal counsel on a full spectrum of corporate, commercial, and regulatory matters including guidance regarding appropriate risk allocation for strategic and core business initiatives.
• Coordinate with internal and external resources to provide support, including risk assessment and contract drafting, for data privacy and cyber security matters.
• Establish a strong rapport and working relationship with Inspira teams to help drive the delivery of effective and high-quality legal services appropriately linked to the Company's business objectives.
• Monitor and proactively communicate legal trends, industry standards and best practices for topics that could affect the Company.
• Develop a thorough understanding of, and familiarity with Inspira, and its markets, customers, and competitors, in order to identify trends and formulate structures and strategies accordingly.
• Establish a rapport and working relationship with employees at all levels in order to encourage and continue the proactive use of in-house counsel.
• Other duties as assigned.

Preferred Qualifications
Education & Experience:

• 6-10 years of experience with commercial transactions, including experience with technology and SaaS transactions
• Juris Doctorate Degree required

Skills & Abilities:

• Working knowledge of the financial services and consumer directed benefits industries and applicable regulatory regimes

• Experience with some of the following preferred: HSAs and consumer directed benefit products
• Ability to work collaboratively and effectively at all levels of the organization

• Excellent communication and presentation skills

• Strong time and case management skills; ability to shift quickly between substantive areas of law and the requirements of the different lines of business in a fast-paced environment

• Commitment to professionalism

• High level of integrity exercised internally and in representing the firm to outside parties

Other Requirements:

• Infrequent travel (less than 10%)
  • Ability to provide personal transportation from time to time
• Prolonged periods of sitting at a desk and working on a computer

Compensation & Benefits
$160,000 - $215,000 per year