Jobs › TruStage

Counsel, Commercial Transactions (Hybrid)

TruStage · Madison, WI · $111,800–$167,700 a year · Full time

Posted Jun 22, 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 a negotiation where the business wanted to sign quickly and you saw a real risk. How did you handle it?

What they are checking: Whether they can balance deal speed with protection and explain risk in business terms leaders can weigh.

Tell me about a time you managed several contracts with tight deadlines at once. How did you prioritize?

What they are checking: Whether they manage their own workload reliably, which the posting names as a core expectation.

How would you build your knowledge of TruStage's business, products and customers in your first months?

What they are checking: Whether they see business understanding as part of good legal advice rather than an optional extra.

What would you do

A strategic vendor refuses to accept uncapped liability for data breaches. How would you negotiate that?

What they are checking: Whether they can find middle ground like super caps or insurance while protecting the company's real exposure.

How do you decide what to escalate to your managing attorney and what to handle yourself?

What they are checking: Whether they know their limits and use supervision well, which this role explicitly builds in.

The vendor sends back a redline that changes key terms without marking them. What do you do?

What they are checking: Whether they catch unmarked changes through careful comparison and address them directly with the other side.

About the work

Walk me through how you review a vendor's master services agreement for the first time. What do you look at first?

What they are checking: Whether they have a disciplined approach that hits liability, indemnity, data and termination before smaller points.

What contract terms matter most when a vendor will handle personal or financial data for an insurance company?

What they are checking: Whether they know data security, audit rights, breach notice and regulatory cooperation clauses that insurers need.

How do you explain a complex indemnity clause to a business partner with no legal background?

What they are checking: Whether they can make contract terms understandable so the business makes informed decisions.

What's the difference between a limitation of liability and an indemnification clause, and how do they interact?

What they are checking: Whether they understand how these clauses work together, which drives most real risk allocation 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: This position has responsibility for completing assigned legal work for the business of TruStage, focusing primarily on drafting and negotiating commercial transactions documents with strategic vendors and partners. This Position will develop legal expertise and establish primary responsibility and accountability for identified projects and/or legal work. The position has responsibility in assisting in the handling of complex legal matters, under the supervision and guidance of a managing attorney. This individual will also work collaboratively across the organization with business partners, shared service partners, and other attorneys within the Legal Department. Job Responsibilities: • Builds knowledge of the company, processes and customers. • Manages own workload and provides informal guidance to colleagues with less experience; may lead small projects with manageable risks and resource requirements. • Solves moderate problems. • Proposes ideas for process improvements. • Approaches changes with flexibility. • Works independently, receives moderate guidance. • Provide legal advice, opinions and counseling to TruStage. • Determine, investigate, research, and analyze all legal aspects of projects. • Negotiate and draft legal documents including commercial contracts. • Direct, manage and supervise outside counsel. • Develop legal expertise and high degree of knowledge of TruStage. • Develop and interact with key outside contacts. • Participate in cross functional teams, committees, task forces and special projects. • Developing a fundamental understanding of financials and dynamics of the specific TruStage entities/business units to which you provide support. • Translates legal advice into terms that are business focused. 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, three to five years of legal experience with overall expert (or developing expert) status in corporate law and commercial transactions. • Effective negotiation, analysis, reasoning, creativity, and judgment skills. • Excellent written and verbal communication skills. • Effective 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. • Developing knowledge and experience in TruStage operations and corporate affairs, including objectives, strategies, products and programs. • 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. • Accountability • Actively works toward meeting client needs and addressing client issues. Obtains relevant information from the client necessary to address and solve client 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 translate into long term growth and 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. #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: $111,800.00 - $167,700.00 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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