Jobs › TruStage

Senior Counsel, Transactions (Hybrid)

TruStage · Madison, WI · $135,500–$203,300 a year · Full time

Posted Sep 11, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about the most complex commercial negotiation you led. What made it hard and how did you close it?

What they are checking: Whether they have handled senior-level deals with real stakes and can describe their own role in the outcome.

Tell me about a time you mentored a less experienced attorney. What did you focus on?

What they are checking: Whether they develop others, which the leadership part of this senior role requires.

Tell me about a time you built trust with a business partner who originally saw legal as a roadblock.

What they are checking: Whether they can build the partnerships the role names, turning Legal into a trusted advisor instead of a gate.

What would you do

A business leader wants to sign a deal that you think carries too much risk. How do you advise them?

What they are checking: Whether they give clear risk advice while respecting that the business owns the final decision.

Two business units want different terms with the same vendor. How do you resolve it?

What they are checking: Whether they can align internal stakeholders and present one coherent position to the vendor.

How do you decide when to bring in other legal specialists, like privacy or regulatory counsel, on a transaction?

What they are checking: Whether they know where their expertise ends and coordinate across the legal department well.

About the work

Walk me through how you would structure a strategic partnership agreement with a distribution partner for insurance products.

What they are checking: Whether they understand partner deals beyond vendor contracts, including exclusivity, compensation and regulatory roles.

How do you build a contract playbook so business teams and junior attorneys can handle routine deals without you?

What they are checking: Whether they think about scaling legal support through standards and fallbacks instead of reviewing everything personally.

What contract provisions are especially important when a partner will market or service insurance products to members?

What they are checking: Whether they understand licensing, marketing approval, complaint handling and regulatory compliance terms in insurance deals.

How do you handle a technology vendor contract that involves AI or heavy data use?

What they are checking: Whether they stay current on newer risks like data rights, model training and output liability in vendor deals.

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The full job description

As published by TruStage.

At TruStage, we’re on a mission to make a brighter financial future accessible to everyone. We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Job Purpose: The role of Senior Counsel is for a legal professional who will be responsible for utilizing legal expertise to advise the activities of all levels of management, including all those who are conducting company business. A successful individual filling this Senior Counsel role will effectively build partnerships with business customers, have solid leadership skills and will have expertise and primary responsibility and accountability for the transactional activities with TruStage's strategic partners and vendors, including drafting negotiating, and reviewing commercial contracts. This individual will also work collaboratively across the organization and with business partners, shared services partners, and other attorneys in other areas of responsibility within the legal department. Job Responsibilities: • Ensure protection of the legal rights of TruStage. • Demonstrate proficiency in building relationships, consultant and influence skills. • Partner with clients on business initiatives. • Provide business focused legal options and opinions to facilitate reaching corporate objectives. • Determine, investigate, research, and analyze relevant legal aspects of projects. • Draft, review, and negotiate legal documents, including commercial contracts and related transaction documents. • Direct, manage, and supervise outside counsel • Develop legal expertise and high degree of knowledge of TruStage. • Participate in cross functional teams, committees, task forces and special projects. • Ensure appropriate corporate legal compliance across all areas of the law in collaboration with subject matter experts. • Inform and advise business regarding legal issues to enable informed business decision-making. • Work collaboratively across the Legal Transactions team and other Legal stakeholders to ensure efficient and effective provision of legal services. • Challenge self and others in a continuous-improvement environment. • Demonstrate TruStage corporate values - Do the right thing; Look for a better way; Make a difference; and Be Inclusive. • Utilize and cultivate experience in connecting on a personal level with others; adjusting style as needed to foster this connection; and being sensitive to group dynamics and respected roles. • Proactively listen without interrupting; ask clarifying questions; and effectively use verbal and non-verbal communication. • Cultivate s a fundamental understanding of financials and dynamics of supported business unit(s). The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time. Job Requirements: • Juris Doctor degree and continuing legal education within areas of specialty and responsibility. • Authorized to practice law in the State of Wisconsin or applicable jurisdiction. • Generally, five to eight years of legal experience with overall expert status in corporate law and transactional legal matters including communicating contracting. • Developing knowledge and experience in TruStage operations and corporate affairs, including objectives, strategies, products and programs. • Strong negotiation, analysis, reasoning, creativity, and judgment skills. • Excellent written and verbal communication skills. • Excellent project management and leadership skills. • Demonstrated ability to present oneself and interact with others in a manner that inspires trust and invites consultation. • Demonstrated ability to think and act quickly and perform under significant pressure and deadlines. • Demonstrated sound organizational and planning skills. • Demonstrated ability to work harmoniously and professionally with others. • Technical Skills • Uses legal training to analyze issues, provide legal advice to the company, complete assignments and resolve issues. Demonstrates command of the law and legal framework applicable to assigned subject area(s) and keeps current on legal developments. • Understands and effectively uses available technology to receive requests for advice, document recommendations, and store records. • Monitors trends related to innovation and technology in the legal profession and embraces opportunities for improving department operations and delivery of service. • Demonstrates progressively more sophisticated understanding and analysis of legal processes, legal concepts, legal risks and risk mitigation strategies, and the professional obligations of an in-house counsel role. Uses legal acumen to address increasingly complex business problems. Demonstrates progressively deeper understanding of the company’s business strategies. Assumes increasing responsibility for delivery of legal services and developing effective client relationships. • Accountability • Actively works toward meeting client needs and addressing client issues. Obtains relevant information from the client necessary to address and solve problems. Takes personal responsibility for getting things done and involves others as appropriate. Completes work in a timely manner. Assists others in meeting client, department and company objectives. Manages deadlines appropriately, including actively communicating about and resolving conflicting priorities when necessary. • Professionalism • Acts with integrity and honesty in interactions with others. Follows through on commitments. Adheres to the professional rules of conduct. Models respectful and inclusive behaviors towards others regardless of status or personal differences. Displays sound judgment when making recommendations to others. Listens to others. Balances the needs of relevant stakeholders including business areas, the department and the company. Participates in discussions and shares information and expertise with others. • Provides constructive feedback and willingly accepts feedback from others. • Performs some pro bono or other community service activities. • Business Acumen • Understands business goals and key business drivers to achieve those goals. Prioritizes activities that grow the top line, translate into long term profitability, and support business priorities. • Understands the client’s significant legal and business risks and associated risk management strategies. • Actively monitors industry-changing business and legal developments and trends. • Client Relationship • Demonstrates understanding of client goals and objectives; actively works toward meeting client needs and addressing client issues. Is accessible to clients and maintains regular communication with them. Obtains relevant information from the client necessary to address and solve business problems. Presents advice to the client in a clear and useful manner. Works collaboratively toward shared goals. • Communicates effectively about legal issues one-on-one and to small and large groups. Connects on a personal level with others. Adjusts style as needed to foster connection. Is sensitive to group dynamics and respective roles. Proactively listens without interrupting. Asks clarifying questions. Considers both verbal and non-verbal communication. • Engages with client on business issue as well as legal issues. Partners with clients on business initiatives. Uses information about external legal and business developments to develop recommendations for improvement of company practices and processes. Identifies problems and issues and proactively develops actionable recommendations for improvement. • Possesses a fundamental understanding of financials and dynamics of client’s business area. • Translates legal advice into business-focused terms understood by the client(s). • Actively monitors industry legal and business developments identifies and drives business changes given developments in area of expertise and businesses impacted. #LI-LT If you’re ready to help make a difference, apply today. A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool. This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward. Candidates may choose to opt out of this process. Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status. Base Salary Range: $135,500.00 - $203,300.00 At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan. Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees. We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when “life happens,” you can focus on what’s most important. Accommodation request TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department.

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