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Headquarters: 190 S. LaSalle St., Suite 3800 | Chicago, IL 60603-3432

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Human Resources Generalist

(View all jobs)

Wanted: an Olympically Meticulous Curator of Employee Experience

(also known as a Human Resources Generalist)


We invite you to join Entara and further your career journey with us our Human Resources Generalist. The heart of any company is its people, and here at Entara, we perform the art of cultivating and supporting our people with extreme care. To be top-tier in our service delivery, we must enable our employees by being a world-class employer, period. This type of culture wasn’t built overnight, and it takes considerable tending. There is plenty of qualitative work to be done, but we also need to dot our ‘i’s and cross our ‘t’s.  

This is where our Human Resources Generalist comes into play. Inherent in every employee’s positive experience with Entara is the company’s ability to supply managers and employees alike with the right information, the right guidance, and the right tools. Our Generalist ensures this flow of activities is happening within a framework that honors our standards while adapting thoughtfully to new challenges. Our human resources function doesn’t just check a box; it provides meaningful order and organization inside of company moving at light speed.  

Our ideal Human Resources Generalist is an early-career professional with some solid HR experience under their belts but with a strong ambition to take on more accountability and to gain broad exposure. We’re looking for an enterprising, resourceful team player who wants to work alongside our Director of Finance and Talent Acquisition Manager to keep our team happy and healthy as we scale. Our Generalist bleeds excellence, nails deliverables, and prioritizes communication. Does this sound like you?


(Otherwise known as the fine print, the list of job tasks and responsibilities.)

The Human Resources Generalist will own primary facets of the human resources and workforce management functions of the company. This role includes many traditional responsibilities but offers a uniquely comprehensive level of interaction with employees and managers. Reporting to the Director of Finance, the Human Resources Generalist executes recurring processes for training and surveying, team benefits and compensation,  employee lifecycle management, and company communications. The Human Resources Generalist will also be responsible for working with managers to address individual matters related to employment, career paths, and performance; maintaining and adapting our policies and procedures for a highly-performing remote workforce; and ensuring the integrity of our compliance, documentation, and human capital data.   

  • Employee Engagement and Communications:
    • Oversee the initiatives outlined in the employee engagement strategy and ensure progress and consistency throughout the organization.
    • Execute certain components of our employee engagement plans, such as extension of tools/technology or recognition to employees.
    • Organize the employee wellness program, drive participation, and provide ongoing communications .
    • Compile, edit, and publish firm-wide updates and news related to pay, benefits, workplace, policies, guidelines, and culture, for both real-time and periodic distribution on our designated platforms.
    • Assist with the administrative planning and coordination of employee events.
    • Take the lead on escalated employment issues, communicate appropriately during the course of resolution, apply relevant facts and standards, and work with Director of Finance to promote a positive outcome.
    • Ensure quarterly cadences are followed with respect to the company EOS structure and prepare messaging before and after meetings.
    • Drive consistent adoption of management practices and frameworks with company supervisors.
  • Payroll and Benefits Administration:
    • Handle enrollment/unenrollment in all company benefit plans for new, converted, and departing employees using the HRIS platform and the processes of various benefits providers.
    • Process the semi-monthly company payroll accurately and on time through the HRIS platform, accounting for any earnings, deductions, or changes specific to a particular pay period.
    • Determine and monitor eligibility for employee participation in all company benefit plans
    • Document changes in compensation and benefits using standard processes and ensure all stakeholders receive proper confirmation.
    • Analyze benefits plans annually, in tandem with brokers, to compare, select, and integrate all benefit plans into the HRIS platform and the open enrollment process.
    • Understand trends and usage of compensation and benefits in the company to advisor senior leadership as needed.
    • Research and recommend modifications to benefits and compensation offerings to better serve company needs.
  • Policies and Compliance
    • Maintain and update the Employee Policy Manual as needed to thoroughly reflect all company expectations, guidelines, and policies related to employment, including those items specific to particular states.
    • Draft and maintain various policy and procedure documents as required to provide direction to employees.
    • Monitor the human resources compliance calendar and ensure that all necessary compliance activities (including filings/reporting to government agencies and benefits providers) are completed in a timely fashion.
    • Understand which factors—including updates to federal and local laws—would change the company’s compliance obligations, and work with the Director of Finance to prepare for anticipated changes.
    • Utilize outlets for news and information related to human resources to draw from the latest trends, recommendations, updated requirements, and approaches when crafting company policies and procedures.
    • Discuss and plan for major policy changes or initiatives with the Director of Finance and corporate counsel.
  • Training and Development:
    • Oversee the new employee onboarding workflow and ensure new hires are equipped with the necessary standard resource sets from the company in time for their start date.
    • Assist with the preparation of new hire training plan templates in coordination with hiring managers and perform first-week scheduling for essential training, as needed.
    • Serve as a secondary resource to give new hire orientation training, ensuring a positive first experience with the company.
    • Update and assist with the development of materials or instructions used in new hire training for the employees of various departments.
    • Manage the content and assignments in the LMS training catalog, including required compliance training for new hires.
    • Consult with company managers to identify organizational needs and gaps related to training and development for employees.
    • Track certifications and professional achievements of employees.
    • Manage tools used by managers to assess the skills and professional attainment of technical employees.
  • Surveying and Analysis:
    • Launch and administer periodic and pulsing surveys of various employee groups to gather feedback; report results to designated senior managers.
    • Collaborate with the Talent Acquisition Manager to develop and evolve the methods used to gather information on the employee experience.
    • Review results of surveying to decipher trends that affirm or show opportunities for improvement; prepare summaries and recommendations for managers as needed.
    • Distribute quarterly culture survey results to team after assembling data and the accompanying report.
    • Serve as needed on the company’s Culture Committee to collaborate with employees, keep apprised of thought patterns, and provide guidance on topics related to enhancing company culture.
  • HRIS Management and Documentation
    • Act as subject matter expert and chief administrator of the company HRIS platform and related HR toolsets, performing all necessary tasks, maintaining the integrity of data, and ensuring consistency of process.
    • Audit areas of information to assess accuracy, completeness, relevance, and utility.
    • Manage the flow of information to and from the HRIS platform as needed.
    • Make updates and enhancements to accessible modules of the HRIS platform to optimize the employee experience.
    • Provide training and direction to employees or managers regarding use of the platform.
    • Understand the means and limitations of reporting and quickly respond to management requests for information.
    • Produce and maintain complete and accurate records of employment, including changes in status, eligibility, membership, compensation and benefits, etc.
    • Manage and maintain internal and external HR data to ensure compliance, retention, and privacy obligations are met.
  • Recruitment Assistance:
    • Perform project management for any hiring cases that involve immigration considerations, coordinating the process and communicating with all stakeholders.
    • Assist the Talent Acquisition Manager occasionally with mapping, defining, and planning for new roles in the organization.
    • Provide assistance with targeted sourcing or review of applications for company job roles under the direction of the Talent Acquisition Manager.
    • Provide oversight of Talent Team’s crafting of new or updated job descriptions while collaborating with hiring managers.
    • Evaluate and classify roles based on both internal and agency criteria for applicability of federal and local statute.


  • You have a four-year degree, preferably in a field that’s business oriented. Your affinity for excellence resulted in a high GPA or other academic accolades, and your pursuit for knowledge hasn’t been quenched yet.
  • You have 2-3 years of experience in a dedicated human resources role that included a significant focus on compliance and policy, employee relations, and benefits administration.
  • You are a master of the pen (or keyboard, as it were). Communicating clearly, effectively, and persuasively is an ability you are proud of. You wield words with intention and precision, adapting to a variety of different audiences as needed. You consider your professional communication—and writing, in particular—to be impeccable, effective, and appropriately tailored for the context.
  • You are accomplished with the tools and applications used by HR professionals, such as a modern HRIS system. You also have a knack for learning new software without much formal training; technology in its various forms is something you “get” and understand how to use to your advantage.
  • Your attention to detail and mastery of nuance are manifested in the quality of the work that you produce. You have been entrusted with highly exacting assignments that require precise information and an appreciation for how language and presentation can impact outcomes.
  • You maintain an acute awareness and composure relative to the personal or confidential information that you may come across in your role. You insist on handling confidential information in a professional manner and with the utmost care.
  • You are open to a 45-55 hour work week—for you, it’s about your personal follow through, regardless of the time or steps it takes to get there.
  • You have a dedicated, private space for a home office and already have in place a reliable, private internet connection with at least 25MBPS bandwidth. Public Wi-Fi and shared common spaces do not meet these standards. Entara will supply you with the other necessary tools and hardware to complete your tasks remotely.


  • Judge, not jury. Along with your keen ability to weigh competing input and requirements, you are invested in fully understanding a situation before taking major action. But when it comes time to make a decision or tow a hard line, you are prepared to apply the “law of the land” (in whatever context) and are capable of separating what is right or required from what is going to be most popular with others.
  • Hungry for Knowledge. You’re always on the lookout for the next intellectual addition to your arsenal. You like and want to work in a managed-knowledge organization that promotes from within, and you take these opportunities to glean insight from other members of the team.
  • Corporate Usain Bolt. You’re capable of moving rapidly from task to task without getting rattled. Your desk is clear, your email inbox is empty, your kitchen counters aren’t cluttered, and you never spend 15 minutes tearing around the house in a desperate hunt for your car keys or train pass. You are a lean, mean, well-oiled machine.
  • Accountable & Self-Driven. When you screw up, the person who is most disappointed is always you. You take great pride in the quality of your work and the way in which you deliver it. “Very good” may do for most people, but you’re out for excellence. You are self-motivated with respect to your work because you view it as a reflection of yourself and what you have to offer. You often find that the standards you set for yourself are even higher than what others expect of you, and you learn from your mistakes. You have a refined system for getting things done and the thought of pushing off responsibilities gives you hives.
  • A Trusted Confidant. You are genuinely reliable, respectful, thoughtful, and responsible. You pride yourself on quickly building trust with company leadership, based on your follow through, perceptive listening, and discretion with sensitive information. Your strong backbone and constant eye for professionalism equip you to navigate occasional conflicts and sticky situations while maintaining composure and a business-minded thought process.
  • A Combo Meal. Your style is winningly ambidextrous. While you are known to be creative, social, and improvisational, you also insist on being extremely organized and highly detailed. If Dance Dance Revolution and Microsoft Excel had a love child, it would be you.

We’re serious about these qualities. If they don’t apply to you, you won’t be happy at Entara and we won’t be happy with you. We’ll part ways sooner rather than later.  Let’s avoid all that discomfort by agreeing you won’t contort yourself to meet requirements that just don’t fit. You are who you are, and that’s okay.


Entara is a new kind of IT Managed Services Company. We’re built from the ground up to provide the strategic vision, platforms, processes and people to travel with our clients on the path to their best IT future. We partner with mid-sized organizations to make technology work brilliantly for our clients.

We launched in 2001, as the niche firm YJT Solutions (You Just Trade) helping to solve some of the IT challenges of Chicago’s most intense trading environments. Because of our success working in the financial industry, we branched out to serve other industries over a decade ago.

In 2018, we rebranded to Entara because our company has grown and evolved far beyond its original roots. We are doubling down on making investments in our future to better serve our clients. We are evaluating new toolsets, selecting and integrating the best ones for our future-facing IT Service Management platform, EntaraWorks. We are hiring tomorrow’s leaders, giving them the opportunity to grow beyond what they ever imagined.

We’ve been formally recognized as one of Chicago’s Best and Brightest Companies to Work For since 2017. We’ve also been named in the INC 5000 Top Growing Companies for the past three years! We’re also ranked among MSPmentor’s Top 200 global IT managed services providers, and our influence has expanded beyond the Chicago arena. Our sole focus is excellence. If you are fond of the phrase “close enough,” please don’t apply for this job. Our success is built on developing exceptional relationships with fellow co-workers and clients alike, as we collaboratively chart our best paths forward to the future.


You’ll have a direct impact on our operations, our clients, and our fellow EntaraCorps members. Because of that impact, you’ll get our respect and gratitude for the role you play in making Entara the best it can be.

We’ll provide you with skills, training, responsibility and opportunities to grow, both at Entara and wherever your career takes you in the future. (However, we hope you’ll be successful here for a good, long time.)

We consider mentoring and participating in the continual learning of others to be absolutely essential for both you and your co-workers. You’ll benefit by developing your leadership skills—and by having a replacement ready when you’re ready to move up to another position.

We know that’s not enough.

Here are some of the employee benefits we currently offer:

  • Remote working options!
  • BCBS Gold-level PPO Medical Insurance, premiums paid 100% by us
  • Generous and flexible Paid Time Off policy
  • 401k Corporate Matching Program
  • Reimbursement for approved certification tests and training, seminars, conferences and more
  • Dental Insurance
  • Disability Insurance
  • Life Insurance
  • Healthcare Savings Account (HSA)
  • Dependent Care FSA
  • Tax-advantaged Commuter Benefit Plans
  • Company-wide outings throughout. Recent examples include Ravinia concerts, rooftop barbecues, floating the Chicago River, bowling & bocce, laser tag, and vintage gaming at Headquarters, among other things!

And there’s more…

Virtual “Fridays at Four” and bi-weekly Wellness coaching sessions. Combine that with the chance to work with a variety of clients in some of the most interesting industries around, solve big problems, create new pathways in managed services, and help to lead our clients and ourselves deep into the future, and Entara becomes one IT company that’s hard to beat.

And there’s even more...                                

Our spirit is what makes us different. We work hard. We play hard. We care about each other because we respect where each of us comes from and who we are. We have a more evolved notion of teamwork--solving client problems together and scouring the horizon for new ideas together. We recognize the journey we’re all on, from our clients to ourselves. We’re all at different places on that journey, and each stop requires support, knowledge and courage to move on. It’s why we bring the best tools and support to our clients. And why we treat and reward our EntaraCorps the way we do.