BigTime Software is looking for a full-time HR Generalist to join our People & Culture team. This is a broad, high-impact role that spans the full employee lifecycle — from recruiting and onboarding to performance management, enablement, and HR operations. We're looking for someone who is not only process-oriented and people-first, but also excited about designing and scaling AI-powered People operations. This role will act as a force multiplier for the People team—leveraging AI, automation, and systems thinking to improve efficiency, decision-making, and employee experience.
This is a great opportunity for someone passionate about building great employee experiences and eager to grow across multiple dimensions of People & Culture. This is a hybrid role based at our Chicago headquarters.
What you will be responsible for:
Employee Experience
Own the New Hire Experience, including orientation, our New Hire Ambassador program, and a seamless onboarding process for employees and managers alike
Manage benefits administration, including new hire enrollment, qualifying life events, and monthly insurance invoice audits
Maintain accurate employee records and manage HRIS system administration (address changes, time-off approvals, profile updates, employee change requests)
Support the termination and offboarding process
Manage and update the Employee Referral Bonus Tracker
Be a culture ambassador and embody BigTime's Core Values
Design automated workflows for onboarding, offboarding, and employee lifecycle events
Implement AI-powered self-service solutions (e.g., internal HR chatbot, knowledge base automation)
Recruiting
Support full-cycle recruiting efforts, including job postings, candidate screening, interview scheduling, and coordinating the offer process
Partner with hiring managers to ensure a consistent and positive candidate experience
Help maintain and improve recruiting workflows and tracking
Leverage AI tools to enhance sourcing, screening, and candidate communication workflows
Experiment with AI-assisted interview evaluation, job description optimization, and talent insights
Human Resources
Own and coordinate the performance management process, including review cycles, goal-setting frameworks, and manager/employee communications
Serve as a go-to resource for employees and managers on HR policies, procedures, and people-related questions
Support the Director of People in educating and enforcing HR policies across the organization
Use AI tools to analyze engagement, performance trends, and attrition signals
Support managers with AI-assisted feedback, goal-setting, and performance insights
Enablement
Assist in developing and delivering lightweight enablement content — manager training, onboarding resources, policy guides, and more
Partner with team leads to identify skill or knowledge gaps and help design scalable learning solutions
Maintain and organize a library of People & Culture resources accessible to all employees
Create AI-powered learning content and just-in-time enablement resources
Build scalable knowledge systems (e.g., Notion + AI, internal copilots)
AI & Process Innovation
Proactively identify manual or repetitive People team processes and lead efforts to automate or streamline them using AI tools and agents
Stay current on emerging HR tech, AI tools, and automation best practices — and bring recommendations to the team
Serve as the People team's internal champion for thoughtful, responsible AI adoption
Our ideal candidate will have:
Bachelor's degree or equivalent experience
2+ years of experience in an HR, People Operations, or related role
Demonstrated interest or experience in recruiting, HR, or enablement
Curiosity and enthusiasm for AI tools, automation, and process improvement
Excellent verbal and written communication skills
Strong interpersonal and customer service orientation
Exceptional organizational skills and attention to detail
Ability to manage multiple priorities in a fast-paced, high-growth environment
Proficiency with Microsoft Office Suite, Google Workspace, or related tools; HRIS experience a plus
Working at BigTime has its benefits!
Competitive salary and bonus potential
Company-paid benefits, including medical, dental, vision, disability, and life insurance
Generous time off and paid company holidays
Company-provided latest technology & software tools
Hybrid schedule (combination of remote and in-office at our Chicago HQ)
Compensation & Benefits
The pay range for this position is $70,000.00-$80,000.00 annually. Actual compensation will be determined based on experience, skills, and qualifications.
Equal Opportunity Employer
BigTime Software, Inc. is an equal opportunity employer and is committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion, sex, gender identity, sexual orientation, national origin, age, disability, veteran status, or any other protected status under applicable law.
Reasonable Accommodations
If you require a reasonable accommodation during the application or interview process, please contact Elaina Johnsen, Senior Manager of People & Culture ([email protected]).
Employment Eligibility
All applicants must be authorized to work in the United States.
Additional Information
This position may be subject to a background check in accordance with applicable laws. Employment with BigTime Software, Inc. is at-will and may be terminated at any time, with or without cause or notice.
Skills Required
- Bachelor's degree or equivalent experience
- 2+ years of experience in an HR, People Operations, or related role
- Demonstrated interest or experience in recruiting, HR, or enablement
- Excellent verbal and written communication skills
- Strong interpersonal and customer service orientation
- Exceptional organizational skills and attention to detail
- Proficiency with Microsoft Office Suite, Google Workspace, or related tools
- HRIS experience
BigTime Software, Inc. Compensation & Benefits Highlights
-
Healthcare Strength — Company‑paid medical, dental, and vision are highlighted, and the health plan is described as strong. Wellness‑oriented healthcare additions such as mental health benefits and FSAs further broaden coverage.
-
Leave & Time Off Breadth — Generous time off and holidays are promoted, with flexible PTO, sick days, volunteer time, and two additional “Refresh Days.” Paid parental leave and a post‑parental return‑to‑work program are also included.
-
Wellbeing & Lifestyle Benefits — Perks include weekly lunch stipends or catered meals, snacks and drinks, gym membership access in Chicago, weekly yoga, fitness stipends, commuter/Divvy benefits, and company outings. Structured DEI programming and ERGs are also part of the offering.
BigTime Software, Inc. Insights
What We Do
Leading a successful professional service firm is an art. Running a profitable firm is a business. We understand this because our founder ran an IT Consulting firm for over 15 years. He grappled with the same challenges that professional service firm owners face today. How do I know what my employees are working on? How can I connect time and expenses to clients or projects for billing? What resources do I have available? How can I see relevant reports on the firm’s performance? The list goes on. The problems our founder faced drove the development of an AI-powered professional services automation platform specific to the needs of operational and financial leaders in professional services firms. We know that time tracking is more than timesheets. Time is information. We connect time with every part of your firm’s workflow so that all of the data you’ve collected with BigTime is the basis for metrics-driven reporting that informs your decisions. We live by our founder’s purpose - to help professional service firms combine the art of leadership with the business of being profitable.
Why Work With Us
At BigTime, we foster a culture that values and listens to what employees have to say. We are a high growth company where each employee has the ability to make an impact and develop personally and professionally and grow from within.
Gallery
BigTime Software, Inc. Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
