Job Location:
Chicago, IL

The Transwestern companies together comprise a privately held, diversified real estate services, investment management and development organization.

A unique approach underlies our success. We do business differently by empowering our team members with the resources and independence to deliver extraordinary results to our clients. It’s simple. We start with hiring hard-working, smart, genuinely good people, and organize them in collaborative cross-functional teams. We give them the support to outperform and the freedom to take ownership as they work to exceed our clients’ expectations. We do business differently, and that makes us Transwestern.

The Human Resources Generalist is responsible for assisting with the administration of leaves of absences and recruiting initiatives. 

The HR Generalist will review and approve leaves in compliance with applicable state, local and federal laws, as well as company policies, procedures, and standards. The HR Generalist is responsible for accurately documenting communications and interactions related to leaves in the case management system and online files, and to ensure that on-going claim management is within company service standards and industry best practices. This role will ensure high-level of service is provided to all team members, while handling sensitive and confidential information. 

The HR Generalist will provide support with candidate sourcing, development of candidate pipelines, resume review, candidate pre-screening and candidate engagement all while fostering a collaborative environment to ensure a great candidate experience. The HR Generalist will also assist in a wide range of candidate branding efforts to drive the overall talent strategy for the company.

It is also the responsibility of the HR Generalist not only to exhibit legendary customer service when communicating with tenants, prospective tenants, owners, and vendors but also to focus on productivity and results.


Leave of Absence:

  • Communicate clearly and concisely with team members while identifying their need for leave/ accommodations and educate them on leave concepts, available benefits and next steps.

  • Demonstrate respect, empathy, confidentiality, and understanding for the team member’s circumstance while maintaining professionalism at all times.

  • Ensure that team members are aware of their responsibilities and of any documentation and notice required to qualify for and take leave/accommodation.

  • Handle the leave administration process from the team member’s initial notice of the need for leave to the return to work. This includes gathering and completing all required documentation, determining leave eligibility, designating leave as FMLA-qualifying, requesting medical certification as needed, and accounting for intermittent and reduced schedule leave use.

  • Analyze leave claims to determine eligibility and certification in compliance with local, state and federal guidelines and in coordination with Company policies and standards.

  • Provide efficient and professional follow-up via phone and email to ensure timely processing of leave requests.

  • Maintain communication with team members on leave to facilitate smooth and timely return to work; as needed, relay communication between team members and their manager during leave.

  • Follow through on each case, monitors case duration to ensure receipt of relevant documentation, issues timely and accurate responses, and escalate case when appropriate.

  • As needed, contact medical providers to obtain or clarify medical facts supporting the need for a leave of absence

  • Accurately draft leave of absence correspondence for team member leave notifications, approvals, and requests for medical certifications.

  • Coordinate with Payroll department ensuring compensation transactions (tracking hours used/taken) are accurate to ensure pay is accurate and correct.  Monitor this for the duration of the leave.

  • Partner with Managers and HR Business Partners to determine next steps on leaves that have exhausted state and federal entitlements.

  • Recognize when there is a need to escalate to upper management and/or legal.

  • Organize files and track leave of absence documentation separate from other personnel records. Preserve confidentiality of team member medical documentation and files.

  • Run basic reports to identify upcoming leaves and returns to work, as well as Ad-hoc reports when needed.

  • Maintain knowledge of all applicable leave and accommodation laws including the FMLA, ADA, and other federal, state, and local laws.


  • Partner with Human Resources and hiring managers to assist with the development and the execution of tactical sourcing strategies aimed at generating candidate flow to meet overall recruiting goals, as well as pipelines for upcoming searches

  • Source and review candidate resumes to make sure they align with the job responsibilities.

  • Schedule initial candidate phone screenings and manage interview scheduling.

  • Manage candidate relationships and provide interview status updates with candidates while creating a memorable candidate experience.

  • Monitor the status of active job postings and ensure candidates status is appropriately designated.

  • Audit, update and maintain job requisition and post status.

  • Partner with candidates and HR throughout the interview process, scheduling in-person interviews, conducting manager and candidate debriefs.

  • Assist with generating and maintain reports on key talent acquisition metrics.

  • Assist with miscellaneous projects related to on campus recruiting, summer internship program, employment branding, temporary hiring, and other recruiting activities.

  • Manage Transwestern employee referral program.

  • Support new hire onboarding initiatives.

  • Provide innovative ideas that can support the ongoing growth of the leave of absence process and recruiting.

  • Perform other duties and special projects as assigned.


  • A bachelor’s degree in human resources, business, or related degree field.

  • At least two (2) years of HR or leave of absence administrative experience.

  • Knowledge of state and federal FMLA regulations

  • Experience with Workday and leave of absence case management system preferred.

  • Must have intermediate to advanced Microsoft 365 Word, PowerPoint, and Excel proficiencies.

  • Stay up to date with regulatory changes and industry trends, make recommendations on how to improve our current leave policies and program.

  • Strong analytical and technical ability to create and maintain metrics, reports, and schedules.  

  • Ability to maintain confidential information and have a high degree of accuracy in processing all leave information.

  • Exceptional communication and organization skills, with strong focus on customer service.

  • Time management skills and ability to handle multiple projects, changing priorities and a continually heavy workload.

  • Foster a positive working environment for team members.

  • Excellent customer service skills and ability to communicate complicated processes.

  • Strong interpersonal skills and ability to interact will all levels of the organization with diplomacy and professionalism.

  • Strong desire to succeed in an entrepreneurial environment.





Chicago, IL

We Are Transwestern!

Transwestern’s Guiding Principles are woven into the fabric of our firm and underscore the value of each individual team member. We embrace diversity, equity and inclusion — not only as the right thing to do, but as a reflection of who we are. It is our responsibility and heartfelt desire to create an environment that elevates the human spirit and brings out the best in everyone. Transwestern offers an exciting work environment, competitive salary and excellent benefits, which include medical, dental and vision coverage, as well as a 401(K) plan. Transwestern is an Equal Opportunity Employer.