Jobs › Health Care Service Corporation

Sr Contract Specialist

Health Care Service Corporation · Chicago, IL · $63,300–$114,300 a year · Full time

Posted Oct 2, 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 time you trained a new team member on document drafting.

What they are checking: Whether they can teach detailed work clearly, which this role requires.

Tell me about a time you had to act as the go-between for your team and management on a concern.

What they are checking: Whether they can carry concerns honestly in both directions as a liaison.

Tell me about a judgment call you made on a document without clear guidance.

What they are checking: Whether they use sound independent judgment and know when to ask for help.

What would you do

A group asks for non-standard language in their booklet. How do you review that request?

What they are checking: Whether they can spot risk in custom language and know when to refer it to senior staff.

A teammate keeps making the same error in documents. How do you address it?

What they are checking: Whether they handle peer issues directly and fairly while acting as a lead.

You have several documents due the same day and one is very complex. How do you plan your work?

What they are checking: Whether they manage deadlines realistically and raise risks early.

Another department disagrees with how you drafted a section. How do you work it out?

What they are checking: Whether they communicate across departments to resolve issues without defensiveness.

About the work

Walk me through how you draft an account-specific contract or benefit booklet from a standard template.

What they are checking: Whether they can draft accurately and know which parts can change and which cannot.

How do you set up random audits so they actually catch errors without slowing the team down?

What they are checking: Whether they design quality checks that are practical and find real problems.

How do you make sure the language in a document matches what the group actually purchased?

What they are checking: Whether they verify drafts against source information instead of assuming the template is right.

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The full job description

As published by Health Care Service Corporation.

At HCSC, our employees are the cornerstone of our business and the foundation to our success. We empower employees with curated development plans that foster growth and promote rewarding, fulfilling careers. Join HCSC and be part of a purpose-driven company that will invest in your professional development. Job Summary This position is responsible for drafting account-specific documents; reviewing non-standard document language requests; referring issues to senior staff as required; coordinating and overseeing training of staff; conducting random audits to endure accuracy and consistency; leading day-to-day operations of team; consulting with team and elevating concerns to management; and acting as liaison between staff and management. Required Job Qualifications: *Bachelor degree or 4 years work experience in a position involving independent judgment and initiative. *1 year experience and skills in drafting standard or customized contracts or booklet documents with no guidance *PC experience including Microsoft Office. *Experience in deadline driven environment and completing tasks on time. *Judgment and problem resolution skills. *Verbal and written communication skills to interface with staff from other departments, draft document language and handle issue resolution Preferred Job Qualifications: *Referral preference given to applicants able to take and meet testing criteria. *Experience developing corporate project plans. Skills in project management Are you being referred to one of our roles? If so, ask your connection at HCSC about our Employee Referral process! Pay Transparency Statement: At Health Care Service Corporation, you will be part of an organization committed to offering meaningful benefits to our employees to support their life outside of work. From health and wellness benefits, 401(k) savings plan, pension plan, paid time off, paid parental leave, disability insurance, supplemental life insurance, employee assistance program, paid holidays, tuition reimbursement, plus other incentives, we offer a robust total rewards package for employees. Learn more about our benefit offerings by visiting https://careers.hcsc.com/totalrewards . The compensation offered will vary depending on your job-related skills, education, knowledge, and experience. This role aligns with an annual incentive bonus plan subject to the terms and the conditions of the plan. Flex employees are expected to be in the office a minimum of three days a week. Management will have discretion to modify an employee's weekly schedule for exigent circumstances. HCSC Employment Statement: We are an Equal Opportunity Employment employer dedicated to providing a welcoming environment where the unique differences of our employees are respected and valued. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, protected veteran status, or any other legally protected characteristics. We are a drug-free and smoke-free workplace. Employment may be contingent upon successful completion of drug screening in accordance with applicable law. Base Pay Range $63,300.00 - $114,300.00 Exact compensation may vary based on skills, experience, and location.

Apply at Health Care Service Corporation