Corporate Business Paralegal

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Join Sentry's team as a Corporate Business Paralegal!

Sentry’s Corporate and Transactional Paralegals perform a variety of complex legal activities, including reviewing and helping negotiate a variety of commercial agreements, assisting with maintenance of Sentry’s trademark portfolio, and mergers and acquisitions activities.

What You'll Do

As a Corporate and Transactional Paralegal, you will:

Review and negotiate legal agreements, providing guidance and recommendations to business stakeholders on agreement terms and alternative provisions to resolve differences between the organization and external parties.
Champion the adoption of new legal technologies, including AI, into Sentry’s corporate and transactional practice area by actively reviewing, evaluating, and implementing them into legal workflows. This involves providing thoughtful guidance on responsible technology use while fostering continuous innovation and evolution of processes and tools.
Assist in the due diligence and drafting of documents from beginning to end for complex commercial transactions, mergers and acquisitions, and restructuring. Draft closing checklists and ancillary agreements necessary for closing, review regulatory requirements and advise on necessary approvals thereof, draft filings and coordinates with internal regulatory groups and regulatory authority to ensure all necessary approvals are received and processes are finalized.
Manage and advise on all aspects of Sentry’s patent and trademark portfolio, including assisting with the procurement and enforcement of Sentry’s intellectual property rights.
Research and interpret statutory and case law for various specialized areas, such as insurance regulatory, economic sanctions laws (OFAC, Export Controls, FinCen, AML), financial institutions, investments and securities, privacy, environmental laws, employment, advertising and marketing, hospitality, and intellectual property.
Draft, implement, and oversee processes for company policies, governance documents, and regulatory filings to ensure adherence to internal and external requirements. Focus areas may include, but are not limited to board minutes/resolutions, Corporate Governance Annual Disclosure Statements, Corporate Authority to do Business, Securities, code of conduct & ethics, and conflicts of interest.
Research and advise business stakeholders on contract interpretation, intellectual property rights, and regulatory compliance matters to maintain adherence with state and federals laws relevant to operations.
Respond to business area questions regarding the interpretation of applicable laws to ensure the business maintains a strong understanding.

What it Takes

Bachelors Degree or equivalent work experience.
Minimum of 5 years related work experience.
American Bar Association-certified paralegal training or equivalent work experience.
Advanced knowledge of case management, litigation processes and knowledge of, and ability to perform legal research.
Excellent communication skills with demonstrated experience producing written communication in a clear, concise, organized, and convincing manner for intended audience.
Strong interpersonal skills with the ability to effectively work with all level of company management, stakeholders, customers, and outside counsel.
Strong organizational skills.
Ability to protect and maintain confidentiality and privilege of all legal matters including the most confidential human resources, business, and Board matters handled within the Company.

What You'll Receive

At Sentry, your total rewards go beyond competitive compensation. Below are some benefits and perks that you’ll receive.

Sentry is happy to offer flexibility through a scheduled Hybrid work model. Monday and Friday work from home if you choose to, Tuesday through Thursday you’ll work in office.
As a Sentry associate, you will have an in-office workspace and materials for your home office. In addition to the laptop, you will receive prior to your start, Sentry will provide equipment for your home office.
Meal Subsidy available for associates who report to an office.
401(K) plan with a dollar for dollar match on your first eight percent, plus immediate vesting to help strengthen your financial future.
Continue your education and career development through Sentry University (SentryU) and utilize our Tuition Reimbursement program
Generous Paid-Time Off plan for you to enjoy time out of the office as well as Volunteer-Time off
Group Medical, Dental, Vision, Life insurance, Parental leave, and our Health and Wellness benefits to encourage a healthy lifestyle.
Well-being and Employee Assistance programs
Sentry Foundation gift matching program to encourage charitable giving.

About Sentry

We take great pride in making Forbes’ list of America’s Best Midsize Employers. A lot of different factors go into that honor, many of which contribute to your job satisfaction.

Our bright future is built on a long track record of success. We got our start in 1904 and have been helping businesses succeed and protect their futures ever since. Because of the trust placed in us, we’re one of the largest and financially strongest mutual insurance companies in the United States. We’re rated A+ by A.M. Best, the industry's leading rating authority.

Our headquarters is in Stevens Point, Wisconsin, with offices located throughout the United States. From sales to claims, and information technology to marketing, we enjoy a rewarding and challenging work environment with opportunities for ongoing professional development and growth.

Get ready to own your future at Sentry. Opportunities await!

Talent Acquisition Specialist

Thank you for your interest in Sentry!

Joe Larsen

Joe.Larsen@sentry.com

Equal Employment Opportunity

Sentry is an Equal Opportunity Employer. It is our policy that there be no discrimination in employment based on race, color, national origin, religion, sex, disability, age, marital status, or sexual orientation.

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5 Questions You Should Ask During the Interview

Here are 5 questions we think you could ask during your interview. Use them as a guide to help you write your own questions.

Remember: Always have at least 5 questions prepared for the interview. If you do not, you run the risk of looking unprepared.

What does success look like in this role, and how is it measured?

Why ask this? You want to ensure you have a clear understanding of expectations before accepting the role. Knowing how success is measured helps you hit the ground running and avoid surprises about performance evaluations. It also signals to the employer that you're results-driven.

Can you describe the team dynamic and the company culture?

Why ask this? Skills and experience matter, but if the work environment isn’t a good fit, you won’t be happy or productive. This question helps you gauge whether the company values collaboration, how teams interact, and whether the culture aligns with your work style and values.

What are the biggest challenges facing the person in this role right now?

Why ask this? Every job has challenges, and it’s better to know them upfront. This helps you assess whether the role is a good fit for your strengths and whether the company is realistic about its expectations. If they hesitate to answer, it could be a red flag.

How does the company support work-life balance and employee well-being??

Why ask this? Burnout is real, and some companies expect employees to sacrifice personal time for the job. By asking this, you’ll get a sense of how they value work-life balance, flexibility, and well-being—things that are crucial for job satisfaction and long-term success.

These questions help you make an informed decision while also showing your professionalism and strategic thinking!

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