Introducing Summer’s first Chief Innovation Officer, Don Weinstein, and Summer’s Advisory Board

May 8, 2024

It’s been a blockbuster few months at Summer. In addition to the $9M in funding and our industry-leading integration with ADP, the company is proud to share two more exciting updates! 

Up first: Summer is thrilled to welcome Don Weinstein, the former Global Chief Product & Technology Officer of ADP, as our first Chief Innovation Officer. 

Formerly the Global Chief Product & Technology Officer at ADP, Don brings a wealth of experience and a proven track record of technological innovation in the workplace. With his deep industry knowledge, Don is ideally positioned to guide Summer in delivering innovative solutions that meet the diverse needs of employers and their workforces.

During his tenure at ADP, Don was responsible for all aspects of ADP’s global technology strategy and delivery. In this role, he gained a comprehensive understanding of the needs of employers, both large and small, and the HCMs trying to serve their diverse human capital management needs. Throughout his career, Don successfully introduced numerous new products and innovations that delivered rapid success in terms of market adoption and revenue acceleration, including ADP Mobile, ADP Analytics and the ADP Marketplace. Before his most recent role, he served as ADP’s Chief Strategy Officer where he incubated several successful new business ventures, including ADP’s Data Solutions business. 

As Summer scales to support over 1,000 employers this year, we know that Don will be an invaluable member of the Summer leadership team. We look forward to the myriad ways in which his decades of experience will contribute to the success of our business and the development of our products. 

We’re also announcing Summer’s Advisory Board. 

In working with employers (currently more than 800 employers including Fortune 500s, hospitals, and state governments and municipalities), we’ve come to understand how important it is to hear directly from HR leaders as we build solutions to meet the needs of rapidly evolving workforces. 

These professionals have unique insight into their employee base and their struggles and concerns, and they understand the needs of the business –– their perspectives are invaluable. HR pros can also be powerful change agents within their own organizations and for the business community at-large, thanks to those insights. 

Summer is incredibly lucky to have made some amazing friends in the HR world along the way, and now eight of these folks are joining us in a more official capacity, as the first iteration of the Summer Advisory Board. These folks will give us rich insights into a truly diverse range of employees, all of whom are grappling with the stress of college costs and student debt in one form or another. They’ll serve as a sounding board for Summer’s product development, a resource for our customers looking to advocate for their employees, and a voice in the industry as the conversations around student debt, college cost and tuition-related benefits heat up. 

With that said, it’s our honor to introduce you to the Summer Advisory Board:


Joe Bosch
Former CHRO of DIRECTV and Tenet Healthcare

Joe, currently serving as an Executive Advisory Board Member to SemperVirens Venture Capital and as a Human Capital Consultant with Optimum Associates, has been working in HR since 1983. He worked for PepsiCo in a variety of HR roles before transferring to Pizza Hut, another PepsiCo company. In 1997, Joe was appointed the Chief People Officer of Pizza Hut. After leaving Pizza Hut, he served as the CHRO for Tenet Healthcare, then Centex Homes, and later, for DIRECTV. He also served as the Interim Chief Human Resource Officer at Mattel, Inc, in 2017. Joe is also a member of the HR Hall of Fame and a Fellow in the National Academy of HR. 


Mike Clementi (Chairman of the Board)
CHRO of PetVet Care Centers and Former CHRO of Unilever 

Mike spent 25+ years at Unilever, working both in the US and internationally in various HR roles.  Most recently he held the title of “EVP/CHRO Global Markets & Organization Transformation.” In 2023, he joined PetVet Care Centers as CHRO, leading the HR function for the fast-growing, purpose-driven organization. His career in HR has led him to a passion for building future-fit businesses that create value and level the playing field for everyone. Mike believes that by focusing on what matters most for our organizations, culture, and talent, we can unlock new levels of performance and create environments where people and teams can thrive.

Mike is also a Board Member for the Jackie Robinson Foundation, which delivers scholarship grants and hands-on mentoring to the next generation of talent in the US.  


Dr. Grace Ingram
Wellbeing Manager of City of Alexandria, Virginia

Dr. Grace Ingram is the Wellbeing Program and Employee Engagement Manager for the City of Alexandria in Northern Virginia. Prior to her role with the City, Dr. Grace was a wellness consultant with Harden & Associates, where she provided wellness program consulting and expertise to over 30 different companies throughout the Southeast region of the U.S. Dr. Ingram holds a Bachelor’s in Biology from Spelman College, a Master’s in Exercise Science with a concentration in Health Promotion from Georgia State University and a Doctorate in Health Science with a concentration in Global Health. Dr. Ingram is a member of the American College of Sports Medicine and is a Certified Exercise Physiologist®. She is also a Certified Worksite Wellness Specialist with the National Wellness Institute.


Dermot O’Brien
Former CHRO of ADP and Former CHRO of TIAA

Dermot was most recently the Chief Transformation Officer at ADP, having served as CHRO at ADP from 2012 until 2018. With close to 20 years reporting to CEOs and over 30 years leading global HR teams, Dermot has deep operating business experience and a proven ability to lead global organizations through transformational change by fostering a culture of collaboration, inclusion, and teamwork. He started his HR career at Morgan Stanley, where he spent nearly 9 years, and later held senior roles at Merrill Lynch before serving as the Executive Vice President, Human Resources at TIAA. In 2018, Dermot was named a Fellow by the National Academy of Human Resources (NAHR).


Cindy Olson
Founder & CEO of the Executive Strategic Alliance

Cindy leads Executive Strategic Alliance, LLC, a community of Executives that offers world-class thought leadership, executive briefings on next generation worktech startups, and a board positioning program. Cindy's passion for building and protecting cultures that foster innovation, values, and engagement stems from her life-changing career as Chief Global Human Resources and Community Relations Officer.


Maggie Ruvoldt
CHRO of Learn Behavioral

Maggie is currently the CHRO at LEARN Behavioral, a national organization dedicated to nurturing the potential of children and young adults with autism and special needs; she’s also an HR Venture Advisor to SemperVirens Venture Capital, where she leverages her more than 30 years of experience in HR roles. Maggie also advises companies (from seed-stage to venture-backed) in the health, wellness, human resources, and education sectors; founders seek her guidance in product development, building for scale, human resources strategy, hyper-growth, and account management. 


Mike Theilmann
EVP & CHRO of Albertsons Companies

Mike joined Albertsons in 2019 and serves as the Company’s Executive Vice President and Chief Human Resources Officer. In leading the Human Resources function, Mike is the company’s resident culture authority and cheerleader. 

Prior to joining the Albersons, Mike was with Heidrick & Struggles, most recently as Global Practice Managing Partner of the Human Resources Officers Practice, working with clients to ensure that HR leaders and their teams were equipped with the right qualifications to lead and manage in this rapidly changing global environment. He also served as Group Executive Vice President of JCPenney, leading human resources, store operations, supply chain management, and communications. Prior to joining JCPenney, Mike had been with Yum Brands and its predecessor PepsiCo since 1993, serving in senior human resources positions throughout the world for Taco Bell, Pizza Hut, Yum corporate and the Yum International division.


Katie Watson
Former CHRO of Solidigm and Gilead Sciences

Katie Watson is a global Human Resources leader with 25 years of experience across life sciences, technology, and investment banking. She was most recently the CHRO of Solidigm Technologies, a $9B spin-off from Intel. She previously spent 17 years at Gilead Sciences, where she led the Human Resources function and partnered closely with the CEO, Board of Directors, and other top-level executives on strategies to enable organizational growth, establish an engaged workforce, and create a mission-based culture that aligns with the company’s core values. 

Katie is a Graduate of Stanford’s Board of Directors’ Governance Program, a Certified Compensation Professional (CCP), and a Certified Executive Coach. She was named one of SF Business Times’ “Most Influential Women in Business 2017.” 

We’re over the moon about what we’ll be able to accomplish with these folks as part of our extended team. If you’re ready to learn more about the impact Summer can have for your employee base grappling with student loan debt and college cost planning, reach out today!

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