People Operations Specialist

| Chicago

About Showpad

At Showpad, personalities and cultures connect across oceans to create something extraordinary. As a top 10 software company in the Inc. 5,000 Europe list, Showpad is changing the game when it comes to sales enablement. Our employees create the engagement and impact that drives our success as we expand globally.

In the morning, we’re drinking San Francisco cold brew coffee with a side of Portland doughnuts – English scones for afternoon tea, and in the evening we’re toasting success with Belgian tripel Westmalle to a Chicago house tune.

Key responsibilities as a People Operations Specialist at Showpad

  • Drive employee onboarding and offboarding processes; identify and administer innovation tools and systems that support rapid scale and growth.
  • Work closely with our third-party PEO to administer Showpad benefits, employee leaves, workman’s compensation and payroll.
  • Own payroll for 75+ employees ensuring that internal reporting systems are optimized and executed accurately.
  • Identify and administer valuable HR and employee engagement programs and processes that continue to build an extraordinary employee experience.
  • Maintain employee records and ensure they are kept accurate and up-to-date.
  • Engage in compensation best practices, programs and systems
  • Ensure enrollment and compliance with federal and state programs (Worker’s Compensation, Unemployment Insurance, California Family and Medical Leave Act, Federal Medical Leave Act, and COBRA) and counsel employees applying for benefits under these programs.
  • Function as an advocate and resource for Showpad employees. Advise staff regarding employment basics and Showpad policies, conferring with counsel as necessary.
  • Partner with our global People operations counterparts to support our global strategies.

Skills we are looking for

  • 3+ years of experience as an HR generalist/People Operations specialist.
  • Knowledge of people analytics, HRIS & ATS systems.
  • High level of organizational, communication and interpersonal skills.
  • Strong analytical and project management skills, proven ability to design clear processes, and detail oriented yet flexible approach to problem solving.
  • Experience implementing people programs including compensation, performance feedback, HR compliance, and professional growth.
  • Deep sense of empathy and ability to communicate across diverse groups.
  • Experience within a fast paced work environment.
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Technology we use

  • Sales & Marketing
    • WordpressCMS
    • SageCRM
    • SalesforceCRM
    • MarketoLead Gen


Centrally located in the Loop and easy to get to for all commuters. Plus, right above Revival Food Hall, there are plenty of delicious lunch options.
125 S Clark Street , Chicago, IL 60603

Insider's spotlight

What’s the vibe like in the office?

The vibe in our Chicago office is unlike any other startup I've ever been a part of. Everyone is smart, humble and effective. Even though we are all busy, everyone is always willing to offer help or guidance - even if it outside of their wheelhouse. We all genuinely enjoy each other's company and want to see our teammates succeed.


Office Manager

How do you collaborate with other teams in the company?

Collaboration is absolutely key for my team, since we’re tasked with bringing many different groups together. And as an international organization, we’re building relationships not only across departments, but across the world too. The key for us is to show how we provide value and prove how our collaboration impacts both revenue and culture.


Head of Global Business Development and Alliances

What makes someone successful on your team?

On my team, we grit, we grind. We’re resilient and ambitious. We do what it takes to succeed, while ensuring we maintain a thoughtful and genuine approach. We know the buyer experience starts with us and the people that succeed are equal parts authentic and motivated.


Senior Manager of Sales Development

We’re building the future of sales & marketing success, by empowering sales & marketing teams to sell the way buyers want to buy. We’re delivering a better buyer experience, intelligent sales content and an analytics-powered platform that’s smarter than traditional sales enablement.


President & COO

What are Showpad Perks + Benefits

Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Retirement & Stock Options Benefits
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Some Meals Provided
Happy Hours
Pet Friendly
Fitness Subsidy
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