February

11th

2026

7:00pm

—

10:00pm

2026 Rippling on the Road Chicago

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2026 Rippling on the Road Chicago

June

–

June

2025

Rippling on the Road returns to Chicago!

Join us live and in-person for our future of work conference. Two days full of insights that will challenge how you think about work - and give you the tools to do it better. You’ll meet HR pros, IT execs, and finance leaders for live events, 1:1 product demos, and brand-new ways you can streamline everything you do. Passes are free for customers, $199 for all others - or claim a free pass with an invite code.

The Future of Work Conference

Here is your chance to see the future, operate leaner, smarter, and faster, & build your community.

Join us for

- Two days of tactical sessions, not just ideas
- New playbooks for streamlining HR, IT and Finance
- A first look at new Rippling products transforming work
- Hands-on demos with Rippling product teams
- 1:1 consults to solve your toughest business problems
- Live insights from Rippling experts and industry leaders
- New connections, a professional headshot, and swag

We look forward to having you join us in Chicago!

The countdown begins

Name: 2026 Rippling on the Road Chicago
Start: 2026-03-11T09:30:00-04:00
End: 2026-03-12T17:00:00-04:00
Location: Convene Willis Tower

The Final Countdown!

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Wednesday, March 11th

9:30 AM

Registration Opens

Get settled before content kicks off! Take a headshot while you're looking fresh, meet with our partner sponsors, check out the Rippling product and enjoy a light breakfast.

10:15 AM – 12:00 PM

General Sessions

Rippling 2.0 is here. Learn about how we solve your toughest business problems in one workforce operating system. Plus you'll get a first look at our newest Rippling products launching soon, directly from our COO, Matt MacInnis.

12:00 PM – 1:15 PM

Lunch + Rippling Expo

Connect with your peers over lunch and check out our Rippling Expo with partners across all areas of your business operations. Plus get answers to your toughest questions in private consults with product experts.

1:15 PM - 3:00 PM

Expert Sessions + Workshops

Choose your own learning path. Topics include:

• How HR Wins in the Age of AI: Automate the Mundane, Humanize the Complex

• Designing a Talent Advantage: Hiring for Trajectory, Not Experience

• The Hidden Cost of Treating Finance and HR as Separate Back Office Functions

• Why onboarding sucks (even when you're trying your best)

And many more!

3:00 PM – 4:30 PM

General Sessions + Customer Awards

Head back to the main stage to hear from experts in the industry on how teams architect culture, performance, and connection to scale the business.

We'll also be highlighting some of the super users who have leveraged Rippling to fuel their career growth and transform their day-to-day work.

4:30 PM – 6:00 PM

Happy Hour

Unwind and connect with your new community of operators, builders, and future-minded leaders.

Thursday, March 12th

9:30 AM

Registration Opens

Get settled before content kicks off! Take a headshot while you're looking fresh, meet with our partner sponsors, check out the Rippling product and enjoy a light breakfast.

10:15 AM – 11:00 AM

General Sessions

In this fireside chat with Ryan Kaiser, Aly Wagner will share what her career has taught her about resilience, momentum, and architecting your own path - how to make smart bets, recover from setbacks, and design a career that evolves as you do. This is a conversation about ambition, reinvention, and building a career that lasts.

11:00 AM - 2:30 PM

Expert Sessions + Workshops

Choose your own learning path. Topics include:

• Succession Without the Sabotage: 12 Metrics for Building a Unified Empire Across HR, IT, and Finance

• Get a Seat at the Table: How AI and Employee Experience Help HR Earn Influence

• Networking Table Talks

• The Rippling Rundown: 2026 Product Roadmap

Lunch will be available from 12 - 1 PM and the Rippling Expo, headshots, and 'Office Hours' with our Rippling experts will remain open throughout the day for you to design a day that provides the most value to enhance the way you work.

Speakers

Matt MacInnis

Chief Product Officer, Rippling

Matt MacInnis is President and Chief Product Officer of Rippling. He leads the development efforts behind Rippling's growing portfolio of products, which collectively help the most successful companies in the world run themselves. Matt was previously founder and CEO of mobile publishing company Inkling, and a marketing executive at Apple.

Ally Wagner

Co-Founder + Co-Chair, Bay FC & Olympian

Aly Wagner is a two-time Olympic gold medalist who’s built an extraordinary career by reinventing herself at every turn. From world-class athlete to trailblazing broadcaster to entrepreneur innovating in women's sports to co-founder and co-chair of Bay FC, Aly has navigated high-pressure moments, setbacks, and reinvention on some of the biggest stages in the world.

Sarah Kulhanek

People Operations Manager, brightwheel

Sarah Kulhanek is a strategic People Operations Manager at brightwheel, driving impactful HR initiatives, policy design, and systems improvements. With a background spanning HR generalist and executive support roles, she excels in optimizing processes and supporting organizational growth. She holds a BA in Sport Management from the University of Michigan.

Sara Wong

HR Analyst, Root Inc.

Sara is an HR leader with a decade of experience supporting Seed to Series D startups, including serving as first HR hire at four companies. She builds scalable people strategies for high-growth teams and partner with founders through change. Passionate about empowering employees and advancing the broader People Operations community.

Sharon Ray

Chief Human Resources Officer, HealthSnap

Sharon Ray, Chief HR Officer at HealthSnap, Inc. brings 20+ years of expertise in human capital management across diverse industries. She is passionate about building strong teams, increasing employee engagement and working closely with leaders to enhance company growth, retention and organizational transformations.

Convene Willis Tower

Frequently asked questions

Is there a fee to attend this event?

Rippling on the Road is free for Rippling customers and $199 for non-customers. If you've received an invite code from your Rippling contact, be sure to include that in your registration form above to claim your complimentary pass.

Should I bring my laptop?

Sessions are meant to be interactive, particularly the Rippling Workshops which are designed for customers to follow along in your own Rippling instance. If you'll be participating in those, we encourage you to bring your laptop, follow along and learn new Rippling skills.

Are meals provided?

Yes, breakfast, lunch and snacks will be provided throughout both days. Plus we'll end Day 1 with a happy hour inclusive of drinks and appetizers.

Can I bring my colleagues?

Yes! And remember there will be IT and Finance content tracks also so invite them along. Please send them this page to RSVP so we can account for space and meals accordingly.

Will you offer SHRM or HRCI Recertification Credits?

Rippling is a recertification provider for both SHRM & HRCI. If you're an HRCI member, you can receive 3.5 credits for attending Rippling on the Road. If you're a SHRM member, you'll receive 2.75 Professional Development Credits for attending Day 1 and 2 credits for attending Day 2. We’ll have signs with the codes at the event.

I am traveling to Chicago. Do you have a room block?

Yes, we have an event room block at the Canopy by Hilton Chicago Central Loop. If you would like to book, please do so here by 2/23/2026.

Will I earn CPE Credits for Attending the Accounting Breakout Session?

Yes! Please see below for details on the CPE that you are eligible for:

Field of Study: Management Services
Prerequisites: None
Course Level: Basic
CPE available: 2.0
Instructional Method: Group Live

CPE is provided by CPAacademy.org and will be available within one week of the event. You will be sent a link to your certificate via the email address used to enroll for this event. CPAacademy.org (Sponsor Id#: 111889) is registered with the National Association of State Boards of Accountancy (NASBA) as a sponsor of continuing professional education on the National Registry of CPE Sponsors. State boards of accountancy have final authority on the acceptance of individual courses for CPE credit. Complaints regarding registered sponsors may be submitted to the National Registry of CPE Sponsors through its website: www.nasbaregistry.org.